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Journal articles on the topic 'Wax ester synthesis'

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Published: 4 June 2025

Last updated: 23 June 2025

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1

Kawiński, Adam, Magdalena Miklaszewska, Szymon Stelter, Bartosz Głąb, and Antoni Banaś. "Lipases of germinating jojoba seeds efficiently hydrolyze triacylglycerols and wax esters and display wax ester-synthesizing activity." BMC Plant Biology 21, no. 1 (2021): 50. https://doi.org/10.1186/s12870-020-02823-4.

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<strong>Background: </strong> <i>Simmondsia chinensis</i> (jojoba) is the only plant known to store wax esters instead of triacylglycerols in its seeds. Wax esters are composed of very-long-chain monounsaturated fatty acids and fatty alcohols and constitute up to 60% of the jojoba seed weight. During jojoba germination, the first step of wax ester mobilization is catalyzed by lipases. To date, none of the jojoba lipase-encoding genes have been cloned and characterized. In this study, we monitored mobilization of storage reserves during germination of jojoba seeds and performed detailed characterization of the jojoba lipases using microsomal fractions isolated from germinating seeds.<strong>Results: </strong>During 26 days of germination, we observed a 60–70% decrease in wax ester content in the seeds, which was accompanied by the reduction of oleosin amounts and increase in glucose content. The activity of jojoba lipases in the seed microsomal fractions increased in the first 50 days of germination. The enzymes showed higher activity towards triacylglycerols than towards wax esters. The maximum lipase activity was observed at 60 °C and pH around 7 for triacylglycerols and 6.5–8 for wax esters. The enzyme efficiently hydrolyzed various wax esters containing saturated and unsaturated acyl and alcohol moieties. We also demonstrated that jojoba lipases possess wax ester-synthesizing activity when free fatty alcohols and different acyl donors, including triacylglycerols and free fatty acids, are used as substrates. For esterification reactions, the enzyme utilized both saturated and unsaturated fatty alcohols, with the preference towards long chain and very long chain compounds.<strong>Conclusions: </strong>In in vitro assays, jojoba lipases catalyzed hydrolysis of triacylglycerols and different wax esters in a broad range of temperatures. In addition, the enzymes had the ability to synthesize wax esters in the backward reaction. Our data suggest that jojoba lipases may be more similar to other plant lipases than previously assumed.

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2

Yu, Dan, Ellen Hornung, Tim Iven, and Ivo Feussner. "High-level accumulation of oleyl oleate in plant seed oil by abundant supply of oleic acid substrates to efficient wax ester synthesis enzymes." Biotechnology for Biofuels 11, no. 1 (2018): 53. https://doi.org/10.1186/s13068-018-1057-4.

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<strong>Background: </strong>Biotechnology enables the production of high-valued industrial feedstocks from plant seed oil. The plant-derived wax esters with long-chain monounsaturated acyl moieties, like oleyl oleate, have favorite properties for lubrication. For biosynthesis of wax esters using acyl-CoA substrates, expressions of a fatty acyl reductase (FAR) and a wax synthase (WS) in seeds are sufficient.<strong>Results: </strong>For optimization of the enzymatic activity and subcellular localization of wax ester synthesis enzymes, two fusion proteins were created, which showed wax ester-forming activities in <i>Saccharomyces cerevisiae</i>. To promote the formation of oleyl oleate in seed oil, WSs from <i>Acinetobactor baylyi</i> (<i>Ab</i>WSD1) and <i>Marinobacter aquaeolei</i> (<i>Ma</i>WS2), as well as the two created fusion proteins were tested in Arabidopsis to evaluate their abilities and substrate preference for wax ester production. The tested seven enzyme combinations resulted in different yields and compositions of wax esters. Expression of a FAR of <i>Marinobacter aquaeolei</i> (<i>Ma</i>FAR) with <i>Ab</i>WSD1 or <i>Ma</i>WS2 led to a high incorporation of C<sub>18</sub> substrates in wax esters. The <i>Ma</i>FAR/TM<i>Mm</i>AWAT2-<i>Ab</i>WSD1 combination resulted in the incorporation of more C<sub>18:1</sub> alcohol and C<sub>18:0</sub> acyl moieties into wax esters compared with <i>Ma</i>FAR/<i>Ab</i>WSD1. The fusion protein of a WS from <i>Simmondsia chinensis</i> (<i>Sc</i>WS) with MaFAR exhibited higher specificity toward C<sub>20:1</sub> substrates in preference to C<sub>18:1</sub> substrates. Expression of <i>Ma</i>FAR/<i>Ab</i>WSD1 in the Arabidopsis <i>fad2 fae1</i> double mutant resulted in the accumulation of oleyl oleate (18:1/18:1) in up to 62 mol% of total wax esters in seed oil, which was much higher than the 15 mol% reached by <i>Ma</i>FAR/<i>Ab</i>WSD1 in Arabidopsis Col-0 background. In order to increase the level of oleyl oleate in seed oil of <i>Camelina</i>, lines expressing <i>Ma</i>FAR/<i>Sc</i>WS were crossed with a transgenic high oleate line. The resulting plants accumulated up to >40 mg g seed<sup>−1</sup> of wax esters, containing 27–34 mol% oleyl oleate.<strong>Conclusions: </strong>The overall yields and the compositions of wax esters can be strongly affected by the availability of acyl-CoA substrates and to a lesser extent, by the characteristics of wax ester synthesis enzymes. For synthesis of oleyl oleate in plant seed oil, appropriate wax ester synthesis enzymes with high catalytic efficiency and desired substrate specificity should be expressed in plant cells; meanwhile, high levels of oleic acid-derived substrates need to be supplied to these enzymes by modifying the fatty acid profile of developing seeds.

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3

Ishige, Takeru, Akio Tani, Keiji Takabe, Kazunori Kawasaki, Yasuyoshi Sakai, and Nobuo Kato. "Wax Ester Production from n-Alkanes by Acinetobacter sp. Strain M-1: Ultrastructure of Cellular Inclusions and Role of Acyl Coenzyme A Reductase." Applied and Environmental Microbiology 68, no. 3 (2002): 1192–95. http://dx.doi.org/10.1128/aem.68.3.1192-1195.2002.

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ABSTRACT Acinetobacter sp. strain M-1 accumulated a large amount of wax esters from an n-alkane under nitrogen-limiting conditions. Under the optimized conditions with n-hexadecane as the substrate, the amount of hexadecyl hexadecanoate in the cells reached 0.17 g/g of cells (dry weight). Electron microscopic analysis revealed that multilayered disk-shaped intracellular inclusions were formed concomitant with wax ester formation. The contribution of acyl-CoA reductase to wax ester synthesis was evaluated by gene disruption analysis.

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4

Xu, Juntao, Renwei Zhang, Changsheng Liu, Fang Wang, Kaili Nie, and Li Deng. "The Application of a Rotating Packed Bed Reactor for the Synthesis of High Viscosity Wax Ester." Journal of Biobased Materials and Bioenergy 15, no. 3 (2021): 421–27. http://dx.doi.org/10.1166/jbmb.2021.2052.

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Wax esters are high value-added products and widely used in a broad range of commercial fields. The enzymatic synthesis of wax ester from plant oil is more attractive than the traditional chemical method due to being environmental-friendly and limiting the use of hazardous chemicals. However, the high mass transfer resistance from the high viscous substrate leads to a low conversion and long reaction time in the continues stirred tank reactor (CSTR). The rotating packed bed reactor (RPBR) offers high mass transfer and can be used to enhance the enzymatic wax ester synthesis process. From the results, it could be concluded that the mass transfer was enhanced with the optimization of the centrifugal factor of the RPBR. Under the optimal process conditions, the wax ester yield of 96.4% was obtained after 4 hours reaction, and the half-life of the catalyst corresponded with 64 hours, while nine batches achieved of yields above 90%. The investigation proved that the RPBR is an attractive and effective reactor for heterogeneous bio-catalysis in high viscosity of 7.39~12.27 Cst at 40 °C.

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5

Lenneman, Eric M., Janet M. Ohlert, Nagendra P. Palani, and Brett M. Barney. "Fatty Alcohols for Wax Esters in Marinobacter aquaeolei VT8: Two Optional Routes in the Wax Biosynthesis Pathway." Applied and Environmental Microbiology 79, no. 22 (2013): 7055–62. http://dx.doi.org/10.1128/aem.02420-13.

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ABSTRACTThe biosynthesis of wax esters in bacteria is accomplished by a unique pathway that combines a fatty alcohol and a fatty acyl coenzyme A substrate. Previousin vitroenzymatic studies indicated that two different enzymes could be involved in the synthesis of the required fatty alcohol inMarinobacter aquaeoleiVT8. In this study, we demonstrate through a series of gene deletions and transcriptional analysis that either enzyme is capable of fulfilling the role of providing the fatty alcohol required for wax ester biosynthesisin vivo, but evolution has clearly selected one of these, a previously characterized fatty aldehyde reductase, as the preferred enzyme to perform this reaction under typical wax ester-accumulating conditions. These results complement previousin vitrostudies and provide the first glimpse into the role of each enzymein vivoin the native organism.

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6

MANKURA, Mitsumasa, and Mitsu KAYAMA. "Wax Ester Synthesis by Carp Hepatopancreas Preparation." Journal of Japan Oil Chemists' Society 36, no. 4 (1987): 244–53. http://dx.doi.org/10.5650/jos1956.36.244.

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7

Aizouq, Mohammed, Helga Peisker, Katharina Gutbrod, Michael Melzer, Georg Hölzl, and Peter Dörmann. "Triacylglycerol and phytyl ester synthesis inSynechocystissp. PCC6803." Proceedings of the National Academy of Sciences 117, no. 11 (2020): 6216–22. http://dx.doi.org/10.1073/pnas.1915930117.

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Cyanobacteria are unicellular prokaryotic algae that perform oxygenic photosynthesis, similar to plants. The cells harbor thylakoid membranes composed of lipids related to those of chloroplasts in plants to accommodate the complexes of photosynthesis. The occurrence of storage lipids, including triacylglycerol or wax esters, which are found in plants, animals, and some bacteria, nevertheless remained unclear in cyanobacteria. We show here that the cyanobacteriumSynechocystissp. PCC6803 accumulates both triacylglycerol and wax esters (fatty acid phytyl esters). Phytyl esters accumulate in higher levels under abiotic stress conditions. The analysis of an insertional mutant revealed that the acyltransferase slr2103, with sequence similarity to plant esterase/lipase/thioesterase (ELT) proteins, is essential for triacylglycerol and phytyl ester synthesis inSynechocystis. The recombinant slr2103 enzyme showed acyltransferase activity with phytol and diacylglycerol, thus producing phytyl esters and triacylglycerol. Acyl-CoA thioesters were the preferred acyl donors, while acyl-ACP (acyl carrier protein), free fatty acids, or galactolipid-bound fatty acids were poor substrates. The slr2103 protein sequence is unrelated to acyltransferases from bacteria (AtfA) or plants (DGAT1, DGAT2, PDAT), and therefore establishes an independent group of bacterial acyltransferases involved in triacylglycerol and wax ester synthesis. The identification of the geneslr2103responsible for triacylglycerol synthesis in cyanobacteria opens the possibility of using prokaryotic photosynthetic cells in biotechnological applications.

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8

Holtzapple, Erik, and Claudia Schmidt-Dannert. "Biosynthesis of Isoprenoid Wax Ester in Marinobacter hydrocarbonoclasticus DSM 8798: Identification and Characterization of Isoprenoid Coenzyme A Synthetase and Wax Ester Synthases." Journal of Bacteriology 189, no. 10 (2007): 3804–12. http://dx.doi.org/10.1128/jb.01932-06.

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ABSTRACT Marinobacter hydrocarbonoclasticus DSM 8798 has been reported to synthesize isoprenoid wax ester storage compounds when grown on phytol as the sole carbon source under limiting nitrogen and/or phosphorous conditions. We hypothesized that isoprenoid wax ester synthesis involves (i) activation of an isoprenoid fatty acid by a coenzyme A (CoA) synthetase and (ii) ester bond formation between an isoprenoid alcohol and isoprenoyl-CoA catalyzed, most likely, by an isoprenoid wax ester synthase similar to an acyl wax ester synthase, wax ester synthase/diacylglycerol acyltransferase (WS/DGAT), recently described from Acinetobacter sp. strain ADP1. We used the recently released rough draft genome sequence of a closely related strain, M. aquaeolei VT8, to search for WS/DGAT and acyl-CoA synthetase candidate genes. The sequence information from putative WS/DGAT and acyl-CoA synthetase genes identified in this strain was used to clone homologues from the isoprenoid wax ester synthesizing Marinobacter strain. The activities of the recombinant enzymes were characterized, and two new isoprenoid wax ester synthases capable of synthesizing isoprenoid ester and acyl/isoprenoid hybrid ester in vitro were identified along with an isoprenoid-specific CoA synthetase. One of the Marinobacter wax ester synthases displays several orders of magnitude higher activity toward acyl substrates than any previously characterized acyl-WS and may reflect adaptations to available carbon sources in their environments.

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9

Gunawan, Erin Ryantin, and Dedy Suhendra. "FOUR-FACTOR RESPONSE SURFACE OPTIMIZATION OF THE ENZYMATIC SYNTHESIS OF WAX ESTER FROM PALM KERNEL OIL." Indonesian Journal of Chemistry 8, no. 1 (2010): 83–90. http://dx.doi.org/10.22146/ijc.21653.

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The synthesis of wax ester using refined, bleached and deodorized (RBD) palm kernel oil (PKO) and oley alcohol catalyzed by Lipozyme IM was carried out. Response surface methodology (RSM) based on a five-level, four-factor central composite rotatable design (CCRD) was used to evaluate the interactive effects of synthesis, of reaction time (5-20 h), temperature (20-50 oC), amount of enzyme (0.1-0.2 g) and substrate molar ratio (palm kernel oil to oleyl alcohol, 1:1-1:5) on the percentage yield of wax esters. The optimum condition conditions derived via RSM were reaction time 8.46 h, temperature 44.4 oC, amount of enzyme 0.182 g, substrate molar ratio 1 to 3.7. The actual experimental yield was 92.9 % under optimum condition, which good accordance to the maximum predicted value of 92.4 %. Keywords: response surface methodology, central composite rotatable design, palm kernel oil, lipozyme, alcoholysis, wax ester

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10

Gao, Xiang, Yuandan Zhang, Zhe Li, Xinmin Wang, and Yingna Du. "Study on synthesis and properties of polyacrylate wax inhibitor." Journal of Physics: Conference Series 2723, no. 1 (2024): 012013. http://dx.doi.org/10.1088/1742-6596/2723/1/012013.

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Abstract Synthesis and properties of polyacrylate ester paraffin inhibitior based on polyacrylate ester start from dodecanol, tetradecanol, hexadecanol, octadecanol respectively were introduced in this paper. Hexadecyl polyacrylic showed the most potent paraffin inhibition, and then the optimum reaction condition of it was ascertained. The percentage inhibition of hexadecyl polyacrylic, synthesized under the optimized conditions, reached to 79.3%. Then crosslinked polyacrylate ester paraffin inhibitiors were synthesized and screened by static wax precipitation experiment, and find the percentage inhibition of crosslinked hexadecyl polyacrylic reached to 88.4%.

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11

Dunstone, RL, A. Benzioni, ML Tonnet, P. Milthorpe, and A. Shani. "Effect of Temperature on the Synthesis of Jojoba Wax." Functional Plant Biology 12, no. 4 (1985): 355. http://dx.doi.org/10.1071/pp9850355.

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Seed was collected from jojoba [Simmondsia chinensis (Link) Schneider] plants growing at three field sites in two years. The wax percentage was determined by nuclear magnetic resonance and the compositions of the wax and the ethanolysis products (one site only) were determined by gas chromatography. The mean wax concentration varied from 49.2 to 55.1% over all sites and years. The percentage of long-chain wax esters (>C40) decreased linearly with increase in mean maximum temperature during the period of linear seed growth (r� = 0.93). The decrease in long-chain esters was associated with a decrease in the C22 and C24 fatty acids and alcohols. Data from controlled environment studies and from field studies were used to assess the effect of temperature on the percentage elongation, reduction and esterification of acyl-CoAs of carbon lengths 18-22. High temperature lowered the specificity for elongation of C20-C22 and of C22-C,24 and increased the specificity for reduction of the C20 acid to its corresponding alcohol. The amount of C42 wax ester was greater than would be expected by random association of the alkoxy-acyl groups but this preference was not as great at high temperatures.

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12

MANKURA, Mitsumasa, and Mitsu KAYAMA. "Synthesis and Hydrolysis of Wax Ester in Mullet." Journal of Japan Oil Chemists' Society 38, no. 5 (1989): 394–404. http://dx.doi.org/10.5650/jos1956.38.394.

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13

Gunawan, Erin Ryantin, and Dedy Suhendra. "WAX ESTERS PRODUCTION BY ALCOHOLYSIS OF PALM OIL FRACTIONS." Indonesian Journal of Chemistry 8, no. 3 (2010): 356–62. http://dx.doi.org/10.22146/ijc.21591.

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The lipase synthesis of wax esters using palm oil fractions (palm oil and palm kernel oil) and long chain alcohol as substrates was carried out. The present work focuses on the synthesis of wax esters using Lipozyme. Five parameters such as reaction time, temperature, amount of enzyme, molar ratio of substrates and various organic solvents of the reaction system were investigated. The optimum yields were achieved at the reaction temperature of 40 - 50 °C for palm oil (PO) and 40 °C for palm kernel oil (PKO) alcoholysis, a reaction time of 5 - 7 h for PO and 7 - 10 h for PKO alcoholysis, 0.15 g of enzyme for both PO and PKO alcoholysis, molar ratio at 3:1 (alcohol: PO or PKO), and the best solvent for the reactions was hexane. Percentage yields of esters obtained at these optimum reaction conditions was 83% refined, bleached and deodorized (RBD) palm oil alkoholysis and 87% for RBD palm kernel oil alcoholysis respectively Keywords: palm oil, palm kernel oil, enzymatic, alcoholysis, wax ester, oleyl alcohol

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14

Berghuis, Nila Tanyela, Zayed Abdulmalik Marwan, Agus Astra Pramana, and Jati Arie Wibowo. "Synthesis of Oleic Acid Derivatives as Pour Point Depressant (PPD)." Jurnal Kimia Sains dan Aplikasi 28, no. 1 (2025): 23–30. https://doi.org/10.14710/jksa.28.1.23-30.

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Crude oil is widely used worldwide as an energy source in various fields. Over the years, crude oil production has decreased due to one major problem that continues to occur, namely wax deposition. Wax deposits tend to occur due to the composition of the crude oil itself. Crude oil mostly consists of large amounts of hydrocarbon compounds, such as paraffins. Therefore, an additive, such as a pour point depressant (PPD), is needed to inhibit or prevent wax formation. This study compares the performance of various PPDs synthesized using oleic acid as a base material. The esterification of oleic acid with alcohols yielded PPD-Ester Butanol (96.72%) and PPD-Ester Decanol (72.21%). Further esterification with oleic acid resulted in PPD-Ester Butanol + Oleic Acid (47.30%) and PPD-Ester Decanol + Oleic Acid (22.56%). These derivatives can undergo additional reactions, such as epoxidation, diol formation, and esterification, to produce a PPD. Pour point measurements on crude oil samples were conducted following ASTM D-5853. The blank sample had a pour point of 39°C. PPD-Ester Decanol reduced the pour point by 3°C, while all PPD-Esters further esterified with oleic acid lowered it by 9°C. Chemical characterization via FTIR analysis confirmed the presence of C=C, C=O, and aliphatic C-H functional groups. GC-MS analysis of PPD-Ester Decanol + Oleic Acid (decyl 9-monooleate, 10-hydroxy oleate) identified three major compounds: 1-decanol, oleic acid, and decyl oleate. Physical characterization revealed that the synthesized PPDs had densities ranging from 850 to 1,066 kg/m3.

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15

Wahlen, Bradley D., Whitney S. Oswald, Lance C. Seefeldt, and Brett M. Barney. "Purification, Characterization, and Potential Bacterial Wax Production Role of an NADPH-Dependent Fatty Aldehyde Reductase from Marinobacter aquaeolei VT8." Applied and Environmental Microbiology 75, no. 9 (2009): 2758–64. http://dx.doi.org/10.1128/aem.02578-08.

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ABSTRACT Wax esters, ester-linked fatty acids and long-chain alcohols, are important energy storage compounds in select bacteria. The synthesis of wax esters from fatty acids is proposed to require the action of a four-enzyme pathway. An essential step in the pathway is the reduction of a fatty aldehyde to the corresponding fatty alcohol, although the enzyme responsible for catalyzing this reaction has yet to be identified in bacteria. We report here the purification and characterization of an enzyme from the wax ester-accumulating bacterium Marinobacter aquaeolei VT8, which is a proposed fatty aldehyde reductase in this pathway. The enzyme, a 57-kDa monomer, was expressed in Escherichia coli as a fusion protein with the maltose binding protein on the N terminus and was purified to near homogeneity by using amylose affinity chromatography. The purified enzyme was found to reduce a number of long-chain aldehydes to the corresponding alcohols coupled to the oxidation of NADPH. The highest specific activity was observed for the reduction of decanal (85 nmol decanal reduced/min/mg). Short-chain and aromatic aldehydes were not substrates. The enzyme showed no detectable catalysis of the reverse reaction, the oxidation of decanol by NADP+. The mechanism of the enzyme was probed with several site-specific chemical probes. The possible uses of this enzyme in the production of wax esters are discussed.

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Al-Arafi, Naowara, Nadia Salih, and Jumat Salimon. "SYNTHESIS OF OLEYL OLEATE WAX ESTER USING ACIDIC HETEROGENEOUS CATALYSTS." Rasayan Journal of chemistry 14, no. 03 (2021): 1809–15. http://dx.doi.org/10.31788/rjc.2021.1436222.

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Kalscheuer, Rainer, Heinrich Luftmann, and Alexander Steinbüchel. "Synthesis of Novel Lipids in Saccharomyces cerevisiae by Heterologous Expression of an Unspecific Bacterial Acyltransferase." Applied and Environmental Microbiology 70, no. 12 (2004): 7119–25. http://dx.doi.org/10.1128/aem.70.12.7119-7125.2004.

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ABSTRACT The bifunctional wax ester synthase/acyl-coenzyme A:diacylglycerol acyltransferase (WS/DGAT) is the key enzyme in storage lipid accumulation in the gram-negative bacterium Acinetobacter calcoaceticus ADP1, mediating wax ester, and to a lesser extent, triacylglycerol (TAG) biosynthesis. Saccharomyces cerevisiae accumulates TAGs and steryl esters as storage lipids. Four genes encoding a DGAT (Dga1p), a phospholipid:diacylglycerol acyltransferase (Lro1p) and two acyl-coenzyme A:sterol acyltransferases (ASATs) (Are1p and Are2p) are involved in the final esterification steps in TAG and steryl ester biosynthesis in this yeast. In the quadruple mutant strain S. cerevisiae H1246, the disruption of DGA1, LRO1, ARE1, and ARE2 leads to an inability to synthesize storage lipids. Heterologous expression of WS/DGAT from A. calcoaceticus ADP1 in S. cerevisiae H1246 restored TAG but not steryl ester biosynthesis, although high levels of ASAT activity could be demonstrated for WS/DGAT expressed in Escherichia coli XL1-Blue in radiometric in vitro assays with cholesterol and ergosterol as substrates. In addition to TAG synthesis, heterologous expression of WS/DGAT in S. cerevisiae H1246 resulted also in the accumulation of fatty acid ethyl esters as well as fatty acid isoamyl esters. In vitro studies confirmed that WS/DGAT is capable of utilizing a broad range of alcohols as substrates comprising long-chain fatty alcohols like hexadecanol as well as short-chain alcohols like ethanol or isoamyl alcohol. This study demonstrated the highly unspecific acyltransferase activity of WS/DGAT from A. calcoaceticus ADP1, indicating the broad biocatalytic potential of this enzyme for biotechnological production of a large variety of lipids in vivo in prokaryotic as well as eukaryotic expression hosts.

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18

Al-Arafi, Naowara, Nadia Salih, and Jumat Salimon. "Synthesis, Characterization and Optimization of Oleyl Oleate Wax Ester Using Ionic Liquid Catalysts." Indonesian Journal of Chemistry 21, no. 3 (2021): 659. http://dx.doi.org/10.22146/ijc.59694.

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In this work, the synthesis of oleyl oleate wax ester using Brønsted acidic ionic liquid catalysts was carried out. Confirmation of oleyl oleate molecular structure has been performed using FTIR, NMR, and ESI-MS spectroscopies. The ability of ionic liquid catalysts for catalyzing the esterification reaction of oleic acid and oleyl alcohol to produce oleyl oleate was optimized. The ionic liquid catalyst ([NMP][CH3SO3]) was found to be the best catalyst for the esterification reaction of oleic acid and oleyl alcohol compared with the other acidic ionic liquids studied. The optimal reaction conditions were determined at a reaction time of 8 h; oleic acid to oleyl alcohol mole ratio of 1:1; ([NMP][CH3SO3]) with 9.9 wt.%; and reaction temperature of 90 °C. Under these conditions, the percentage yield of oleyl oleate wax ester was 86%.

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Papadaki, Aikaterini, Vasiliki Kachrimanidou, Ioanna Mandala, and Nikolaos Kopsahelis. "Valorization of Spent Coffee Grounds Oil for the Production of Wax Esters: Enzymatic Synthesis and Application in Olive Oil Oleogels." Gels 10, no. 12 (2024): 817. https://doi.org/10.3390/gels10120817.

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Spent coffee grounds, the main by-product of the coffee-brewing process, were valorized as a renewable source of lipids for the synthesis of novel wax esters and as an alternative and sustainable oil-structuring agent for the production of oleogels. The lipase-catalyzed reactions were implemented using fatty alcohols both under solvent-free conditions and with limonene as an environmentally friendly solvent. Wax esters were evaluated for their ability to formulate olive oil oleogels through the determination of the physical properties of oleogels. Results showed that high conversion yields were achieved when cetyl and behenyl alcohols were applied under solvent-free conditions, achieving a maximum yield of 90.3% and 91.7%, respectively. In the presence of limonene, the highest conversion yields were 88.9% and 94.5% upon the use of cetyl and behenyl alcohols, respectively. The behenyl wax esters exhibited greater oil-structuring properties, regardless of whether they were derived from solvent or solvent-free conditions. Rheological curves showed that the produced oleogels exhibited a strong gel strength, which was enhanced as the wax ester concentration increased. Frequency sweep curves confirmed the formation of a stable three-dimensional oleogel network and revealed the low dependence of the storage modulus on frequency. Overall, this study demonstrated that producing wax esters from renewable lipid sources has the potential to serve as an effective circular economy paradigm for creating novel oleogels with a broad range of applications.

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Laschat, Sabine, Yana Galeyeva, Michael Morr, Angelika Baro, Manfred Nimtz, and Florenz Sasse. "Ex Chiral Pool Synthesis of (-)-Siphonarienone from a Methyl-Branched Wax Ester." Synthesis 2005, no. 17 (2005): 2875–80. http://dx.doi.org/10.1055/s-2005-872205.

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21

Yang, Yunqiang, Zhili Zhou, Yan Li, et al. "Uncovering the role of a positive selection site of wax ester synthase/diacylglycerol acyltransferase in two closely related Stipa species in wax ester synthesis under drought stress." Journal of Experimental Botany 71, no. 14 (2020): 4159–70. http://dx.doi.org/10.1093/jxb/eraa194.

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Abstract Natural selection drives local adaptations of species to biotic or abiotic environmental stresses. As a result, adaptive phenotypic divergence can evolve among related species living in different habitats. However, the genetic foundation of this divergence process remains largely unknown. Two closely related alpine grass species, Stipa capillacea and Stipa purpurea, are distributed in different rainfall regions of northern Tibet. Here, we analyzed the drought tolerance of these two closely related Stipa species, and found that S. purpurea was more resistance to drought stress than S. capillacea. To further understand the genetic diversity behind their adaptation to drought environments, a comprehensive gene repertoire was generated using PacBio isoform and Illumina RNA sequencing technologies. Bioinformatics analyses revealed that differential transcripts were mainly enriched in the wax synthetic pathway, and a threonine residue at position 239 of WSD1 was identified as having undergone positive selection in S. purpurea. Using heterologous expression in the Saccharomyces cerevisiae mutant H1246, site-directed mutagenesis studies demonstrated that a positive selection site results in changes to the wax esters profile. This difference may play an important role in S. purpurea in response to drought conditions, indicating that S. purpurea has evolved specific strategies involving its wax biosynthetic pathway as part of its long-term adaptation to the Qinghai–Tibet Plateau.

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Mankura, Mitsumasa, Mitsu Kayama, and Noriaki Iijima. "The role of phospholipase A2 on wax ester synthesis in carp hepatopancreas preparations." NIPPON SUISAN GAKKAISHI 52, no. 12 (1986): 2107–14. http://dx.doi.org/10.2331/suisan.52.2107.

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23

Isono, Yasuyuki, Hiroshi Nabetani, and Mitsutoshi Nakajima. "Wax ester synthesis in a membrane reactor with lipase-surfactant complex in hexane." Journal of the American Oil Chemists' Society 72, no. 8 (1995): 887–90. http://dx.doi.org/10.1007/bf02542065.

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24

Sirakova, Tatiana D., Chirajyoti Deb, Jaiyanth Daniel, et al. "Wax Ester Synthesis is Required for Mycobacterium tuberculosis to Enter In Vitro Dormancy." PLoS ONE 7, no. 12 (2012): e51641. http://dx.doi.org/10.1371/journal.pone.0051641.

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Radzi, Salina Mat, Rosfarizan Mohamad, Mahiran Basri, et al. "Kinetics of Enzymatic Synthesis of Liquid Wax Ester from Oleic Acid and Oleyl Alcohol." Journal of Oleo Science 59, no. 3 (2010): 127–34. http://dx.doi.org/10.5650/jos.59.127.

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Knez, Željko, Chiara Giulia Laudani, Maja Habulin, and Ernesto Reverchon. "Exploiting the pressure effect on lipase-catalyzed wax ester synthesis in dense carbon dioxide." Biotechnology and Bioengineering 97, no. 6 (2007): 1366–75. http://dx.doi.org/10.1002/bit.21331.

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Stöveken, Tim, Rainer Kalscheuer, Ursula Malkus, Rudolf Reichelt, and Alexander Steinbüchel. "The Wax Ester Synthase/Acyl Coenzyme A:Diacylglycerol Acyltransferase from Acinetobacter sp. Strain ADP1: Characterization of a Novel Type of Acyltransferase." Journal of Bacteriology 187, no. 4 (2005): 1369–76. http://dx.doi.org/10.1128/jb.187.4.1369-1376.2005.

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ABSTRACT The wax ester synthase/acyl coenzyme A (acyl-CoA):diacylglycerol acyltransferase (WS/DGAT) catalyzes the final steps in triacylglycerol (TAG) and wax ester (WE) biosynthesis in the gram-negative bacterium Acinetobacter sp. strain ADP1. It constitutes a novel class of acyltransferases which is fundamentally different from acyltransferases involved in TAG and WE synthesis in eukaryotes. The enzyme was purified by a three-step purification protocol to apparent homogeneity from the soluble fraction of recombinant Escherichia coli Rosetta (DE3)pLysS (pET23a::atfA). Purified WS/DGAT revealed a remarkably low substrate specificity, accepting a broad range of various substances as alternative acceptor molecules. Besides having DGAT and WS activity, the enzyme possesses acyl-CoA:monoacylglycerol acyltransferase (MGAT) activity. The sn-1 and sn-3 positions of acylglycerols are accepted with higher specificity than the sn-2 position. Linear alcohols ranging from ethanol to triacontanol are efficiently acylated by the enzyme, which exhibits highest specificities towards medium-chain-length alcohols. The acylation of cyclic and aromatic alcohols, such as cyclohexanol or phenylethanol, further underlines the unspecific character of this enzyme. The broad range of possible substrates may lead to biotechnological production of interesting wax ester derivatives. Determination of the native molecular weight revealed organization as a homodimer. The large number of WS/DGAT-homologous genes identified in pathogenic mycobacteria and their possible importance for the pathogenesis and latency of these bacteria makes the purified WS/DGAT from Acinetobacter sp. strain ADP1 a valuable model for studying this group of proteins in pathogenic mycobacteria.

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Damayanti, Sophi, Vita Yuanita, and Rahmana Emran Kartasasmita. "Optimasi Reaksi Transesterifikasi Minyak Kelapa Sawit (Elaeis guineensis Jacq.) dan Penetapan Kadar Metil Ester Asam Lemak Menggunakan Kromatografi Gas." Acta Pharmaceutica Indonesia 38, no. 1 (2013): 31–36. http://dx.doi.org/10.5614/api.v38i1.5202.

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Indonesia merupakan produsen minyak kelapa sawit (Elaeis guineensis Jacq.) terbesar di dunia. Pengolahan menjadi produk turunannya dapat meningkatkan nilai ekonomi minyak kelapa sawit. Salah satu produk turunannya adalah metil ester asam lemak yang memiliki banyak kegunaan dalam industri pangan, farmasi dan kosmetik. Metil ester asam lemak dihasilkan melalui reaksi transesterifikasi minyak kelapa sawit. Penelitian ini bertujuan untuk menentukan kondisi optimum reaksi transesterifikasi minyak kelapa sawit. Optimasi diamati berdasarkan penetapan kadar metil ester asam lemak secara semikuantitatif menggunakan metode kromatografi gas. Metil ester asam lemak disintesis dari minyak kelapa sawit menggunakan katalis natrium hidroksida dan kalium hidroksida masing-masing pada suhu 40, 50 dan 60 ºC selama 1, 2 dan 3 jam. Metil ester asam lemak yang diperoleh dinetralkan dan dicuci. Baku metil ester asam lemak disintesis dari asam palmitat. Kadar metil ester asam lemak ditentukan menggunakan kromatografi gas dengan kolom DB-Wax 30 m x 0,25 mm, detektor FID, dan kondisi oven pada suhu 50 ºC selama 1 menit, kemudian dinaikkan 25 ºC /menit sampai 200 ºC, lalu dinaikkan kembali 3 ºC /menit sampai 230 ºC dan ditahan selama 18 menit. Kadar asam lemak bebas dari minyak kelapa sawit dan metil ester asam lemak ditentukan dengan metode titrasi. Rata-rata bobot hasil reaksi transesterifikasi menggunakan katalis natrium hidroksida dan kalium hidroksida adalah masing-masing 84,63±2,63 dan 84,25±4,77 g. Rata-rata kadar asam lemak bebas metil ester asam lemak hasil reaksi transesterifikasi menggunakan katalis natrium hidroksida dan kalium hidroksida adalah 0,68±0,03% dan 0,65±0,03 %. Kondisi optimum reaksi transesterifikasi minyak kelapa sawit (Elaeis guineensis Jacq.) menggunakan katalis natrium hidroksida dan kalium hidroksida masing-masing adalah pada suhu 60 ºC selama 1 jam, sebesar 34,20% (b/v) dan pada suhu 50 ºC selama 2 jam, sebesar 32,40% (b/v).Kata kunci: Transesterifikasi, minyak kelapa sawit, metil ester asam lemak, kromatografi gas, katalis basa. AbstractIndonesia is the largest producer of crude palm oil (Elaeis guineensis Jacq.) in the world. Processing into derived products can increase the economic value of crude palm oil. One of the derived products is the fatty acid methyl esters that have many uses in the food, pharmaceuticals and cosmetic industry. Fatty acid methyl ester is produced through transesterification reaction of crude palm oil. The aim of this research is to obtain the optimum condition of transesterification reaction of crude palm oil. Optimization was observed by the assay of fatty acid methyl esters as semi-quantitative using gas chromatography method. Fatty acid methyl esters were synthesized from crude palm oil using catalysts sodium hydroxide and potassium hydroxide respectively at 40, 50 and 60 ºC for 1, 2 and 3 hours. The fatty acid methyl esters obtained were neutralized and washed. The standard of fatty acid methyl ester was made by palmitic acid synthesis. The assay of fatty acid methyl esters was carried out using gas chromatography equipped with 30 m x 0,25 mm DB-Wax column, flame ionization detector (FID), using oven temperature at 50 °C, 1 minute, 25 °C /minute to 200 °C, 3 °C /minute to 230 °C, 18 minutes and determination of free fatty acid content from crude palm oil and fatty acid methyl esters. The average mass of the result of the transesterification reaction using sodium hydroxide and potassium hydroxide as catalyst were 84.63±2.63 and 84.25±4.77 g, respectively. The average of free fatty acid content of fatty acid methyl ester synthesized using sodium hydroxide and potassium hydroxide as catalyst were 0.68±0.03 % and 0.65±0.03 %. The optimum conditions of the transesterification reaction of crude palm oil (Elaeis guineensis Jacq.) using sodium hydroxide and potassium hydroxide as catalyst were at 60 ºC for 1 hour and at 50 ºC for 2 hours, which were 34.20% (w/v) and 32.40% (w/v), respectively.Keywords: Transesterification, crude palm oil, fatty acid methyl ester, gas chromatography, base catalyst.

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Ishige, Takeru, Akio Tani, Yasuyoshi Sakai, and Nobuo Kato. "Long-Chain Aldehyde Dehydrogenase That Participates in n-Alkane Utilization and Wax Ester Synthesis in Acinetobacter sp. Strain M-1." Applied and Environmental Microbiology 66, no. 8 (2000): 3481–86. http://dx.doi.org/10.1128/aem.66.8.3481-3486.2000.

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ABSTRACT A long-chain aldehyde dehydrogenase, Ald1, was found in a soluble fraction of Acinetobacter sp. strain M-1 cells grown onn-hexadecane as a sole carbon source. The gene (ald1) was cloned from the chromosomal DNA of the bacterium. The open reading frame of ald1 was 1,512 bp long, corresponding to a protein of 503 amino acid residues (molecular mass, 55,496 Da), and the deduced amino acid sequence showed high similarity to those of various aldehyde dehydrogenases. Theald1 gene was stably expressed in Escherichia coli, and the gene product (recombinant Ald1 [rAld1]) was purified to apparent homogeneity by gel electrophoresis. rAld1 showed enzyme activity toward n-alkanals (C4 to C14), with a preference for longer carbon chains within the tested range; the highest activity was obtained with tetradecanal. Theald1 gene was disrupted by homologous recombination on theAcinetobacter genome. Although the ald1disruptant (ald1Δ) strain still had the ability to grow on n-hexadecane to some extent, its aldehyde dehydrogenase activity toward n-tetradecanal was reduced to half the level of the wild-type strain. Under nitrogen-limiting conditions, the accumulation of intracellular wax esters in the ald1Δ strain became much lower than that in the wild-type strain. These and other results imply that a soluble long-chain aldehyde dehydrogenase indeed plays important roles both in growth on n-alkane and in wax ester formation in Acinetobacter sp. strain M-1.

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30

Galeyeva, Yana, Michael Morr, Florenz Sasse, et al. "Ex Chiral Pool Synthesis from a Highly Methyl-branched Wax Ester and Biological Properties of (+)-Capensifuranone." Zeitschrift für Naturforschung B 64, no. 6 (2009): 639–45. http://dx.doi.org/10.1515/znb-2009-0608.

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Unnatural (+)-capensifuranone (+)-2 and its epimer (-)-5-epi-capensifuranone 6 were prepared from enantiopure methyl-branched aldehyde 4, employing cyclisation with 3-bromomethacrylic acid to 4-bromofuranones 5a,b followed by Negishi cross coupling. Compound 4 was obtained from the preen-gland wax-derived ester 3 after ozonolysis and reductive work-up. The configuration of 6 was determined via the X-ray crystal structure analysis of a derivative 10. Compounds (+)-2, 5a,b and 6 showed cytotoxic activity against L-929 mouse fibroblasts, and KB-3-1 HeLa and U-937 lymphoma cells.

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MANKURA, Mitsumasa, and Mitsu KAYAMA. "Comparative biochemical studies on plasma cholesterol. III. Wax ester synthesis and hydrolysis in carp plasma." NIPPON SUISAN GAKKAISHI 51, no. 1 (1985): 69–74. http://dx.doi.org/10.2331/suisan.51.69.

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32

Alves, Michelle D., Érika C. Cren, and Adriano A. Mendes. "Kinetic, thermodynamic, optimization and reusability studies for the enzymatic synthesis of a saturated wax ester." Journal of Molecular Catalysis B: Enzymatic 133 (November 2016): S377—S387. http://dx.doi.org/10.1016/j.molcatb.2017.02.011.

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33

Gunawan, Erin Ryantin, Mahiran Basri, Mohd Basyaruddin Abd Rahman, Abu Bakar Salleh, and Raja Noor Zaliha Abd Rahman. "Study on response surface methodology (RSM) of lipase-catalyzed synthesis of palm-based wax ester." Enzyme and Microbial Technology 37, no. 7 (2005): 739–44. http://dx.doi.org/10.1016/j.enzmictec.2005.04.010.

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34

Nakazawa, Masami, Hiroko Ando, Ayusa Nishimoto, et al. "Anaerobic respiration coupled with mitochondrial fatty acid synthesis in wax ester fermentation by Euglena gracilis." FEBS Letters 592, no. 24 (2018): 4020–27. http://dx.doi.org/10.1002/1873-3468.13276.

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35

Galván, Virginia, Federico Pascutti, Natalia E. Sandoval, et al. "High wax ester and triacylglycerol biosynthesis potential in coastal sediments of Antarctic and Subantarctic environments." PLOS ONE 18, no. 7 (2023): e0288509. http://dx.doi.org/10.1371/journal.pone.0288509.

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The wax ester (WE) and triacylglycerol (TAG) biosynthetic potential of marine microorganisms is poorly understood at the microbial community level. The goal of this work was to uncover the prevalence and diversity of bacteria with the potential to synthesize these neutral lipids in coastal sediments of two high latitude environments, and to characterize the gene clusters related to this process. Homolog sequences of the key enzyme, the wax ester synthase/acyl-CoA:diacylglycerol acyltransferase (WS/DGAT) were retrieved from 13 metagenomes, including subtidal and intertidal sediments of a Subantarctic environment (Ushuaia Bay, Argentina), and subtidal sediments of an Antarctic environment (Potter Cove, Antarctica). The abundance of WS/DGAT homolog sequences in the sediment metagenomes was 1.23 ± 0.42 times the abundance of 12 single-copy genes encoding ribosomal proteins, higher than in seawater (0.13 ± 0.31 times in 338 metagenomes). Homolog sequences were highly diverse, and were assigned to the Pseudomonadota, Actinomycetota, Bacteroidota and Acidobacteriota phyla. The genomic context of WS/DGAT homologs included sequences related to WE and TAG biosynthesis pathways, as well as to other related pathways such as fatty-acid metabolism, suggesting carbon recycling might drive the flux to neutral lipid synthesis. These results indicate the presence of abundant and taxonomically diverse bacterial populations with the potential to synthesize lipid storage compounds in marine sediments, relating this metabolic process to bacterial survival.

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36

Chen, Jyh-Ping, and Juin-Bin Wang. "Wax ester synthesis by lipase-catalyzed esterification with fungal cells immobilized on cellulose biomass support particles." Enzyme and Microbial Technology 20, no. 8 (1997): 615–22. http://dx.doi.org/10.1016/s0141-0229(96)00209-8.

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37

Decagny, B., S. Jan, J. C. Vuillemard, et al. "Synthesis of wax ester through triolein alcoholysis: Choice of the lipase and study of the mechanism." Enzyme and Microbial Technology 22, no. 7 (1998): 578–82. http://dx.doi.org/10.1016/s0141-0229(97)00240-8.

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38

Kannisto, Matti, Elena Efimova, Matti Karp, and Ville Santala. "Growth and wax ester production of an Acinetobacter baylyi ADP1 mutant deficient in exopolysaccharide capsule synthesis." Journal of Industrial Microbiology & Biotechnology 44, no. 1 (2016): 99–105. http://dx.doi.org/10.1007/s10295-016-1872-1.

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39

Guncheva, Maya, Emil Tashev, Diana Zhiryakova, Tania Tosheva, and Nadezhda Tzokova. "Immobilization of lipase from Candida rugosa on novel phosphorous-containing polyurethanes: Application in wax ester synthesis." Process Biochemistry 46, no. 4 (2011): 923–30. http://dx.doi.org/10.1016/j.procbio.2011.01.002.

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40

Niu, Kangren, and Kuiyan Song. "Synthesis and Characterization of Maleic Anhydride-Methyl Methacrylate Co-Monomer Grafted Polyethylene Wax for Hot Waxed Wood Process." Materials 15, no. 19 (2022): 6962. http://dx.doi.org/10.3390/ma15196962.

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The beeswax used in Chinese traditional hot waxed wood technology has several drawbacks, such as high price, scarce resources, and poor heat resistance. To expand the application of hot waxing technology in the field of wood decoration and protection, polyethylene wax was modified by a grafted maleic anhydride-methyl methacrylate co-monomer. A type of modified polyethylene wax with low cost, high melting point, high stability, and strong polarity suitable for hot waxed wood was prepared as a replacement for beeswax. The effects of the grafting conditions on the chemical properties, thermal properties, chemical structure, and crystallization properties of modified polyethylene wax were studied and compared to those of beeswax. The results show that maleic anhydride-methyl methacrylate co-monomer grafting can effectively improve the acid value of polyethylene wax. For the ratio of two monomers of 1/1, the total amount of monomer of 8 wt%, the amount of initiator of 2 wt%, the reaction temperature of 150 °C, and the acid value of modified polyethylene wax was consistent with that of beeswax, realizing the simulation of the main chemical properties of beeswax. The thermal stability and melting temperature of the modified polyethylene wax are significantly higher than those of beeswax, its crystal structure is similar to that of beeswax, and the cyclic anhydride groups and ester groups introduced by co-monomer grafting endow it with polar groups that play an important role in the wood hot waxing process.

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Turkish, Aaron R., and Stephen L. Sturley. "The genetics of neutral lipid biosynthesis: an evolutionary perspective." American Journal of Physiology-Endocrinology and Metabolism 297, no. 1 (2009): E19—E27. http://dx.doi.org/10.1152/ajpendo.90898.2008.

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The storage of fatty acids and fatty alcohols in the form of neutral lipids such as triacylglycerol (TAG), cholesteryl ester (CE), and wax ester (WE) serves to provide reservoirs for membrane formation and maintenance, lipoprotein trafficking, lipid detoxification, evaporation barriers, and fuel in times of stress or nutrient deprivation. This ancient process likely originated in actinomycetes and has persisted in eukaryotes, albeit by different molecular mechanisms. A surfeit of neutral lipids is strongly, perhaps causally, related to several human diseases such as diabetes mellitus, obesity, atherosclerosis and nonalcoholic fatty liver disease. Therefore, understanding the metabolic pathways of neutral lipid synthesis and the roles of the enzymes involved may facilitate the development of new therapeutic interventions for these syndromes.

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42

Galeyeva, Yana, Sarah Helbig, Michael Morr, et al. "Total Synthesis and Biological Evaluation of (−)-Pectinatone Employing a Methyl-Branched Wax Ester as Key Building Block." Chemistry & Biodiversity 3, no. 8 (2006): 935–41. http://dx.doi.org/10.1002/cbdv.200690096.

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43

Wenning, Leonie, Christer S. Ejsing, Florian David, Richard R. Sprenger, Jens Nielsen, and Verena Siewers. "Increasing jojoba-like wax ester production in Saccharomyces cerevisiae by enhancing very long-chain, monounsaturated fatty acid synthesis." Microbial Cell Factories 18, no. 1 (2019): 49. https://doi.org/10.1186/s12934-019-1098-9.

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<strong>Background: </strong>Fatty acids (FAs) with a chain length of more than 18 carbon atoms (> C18) are interesting for the production of specialty compounds derived from these FAs. These compounds include free FAs, like erucic acid (C22:1-Δ13), primary fatty alcohols (FOHs), like docosanol (C22:0-FOH), as well as jojoba-like wax esters (WEs) (C38-WE to C44-WE), which are esters of (very) long-chain FAs and (very) long-chain FOHs. In particular, FAs, FOHs and WEs are used in the production of chemicals, pharmaceuticals and cosmetic products. Jojoba seed oil is highly enriched in diunsaturated WEs with over 70 mol% being composed of C18:1–C24:1 monounsaturated FOH and monounsaturated FA moieties. In this study, we aim for the production of jojoba-like WEs in the yeast <i>Saccharomyces cerevisiae</i> by increasing the amount of very long-chain, monounsaturated FAs and simultaneously expressing enzymes required for WE synthesis.<strong>Results: </strong>We show that the combined expression of a plant-derived fatty acid elongase (FAE/KCS) from <i>Crambe abyssinica</i> (<i>Ca</i>KCS) together with the yeast intrinsic fatty acid desaturase (FAD) Ole1p leads to an increase in C20:1 and C22:1 FAs in <i>S. cerevisiae</i>. We also demonstrate that the best enzyme candidate for C24:1 FA production in <i>S. cerevisiae</i> is a FAE derived from <i>Lunaria annua</i> (<i>La</i>KCS). The combined overexpression of <i>Ca</i>KCS and Ole1p together with a fatty acyl reductase (FAR/FAldhR) from <i>Marinobacter aquaeolei</i> VT8 (<i>Ma</i>FAldhR) and a wax synthase (WS) from <i>Simmondsia chinensis</i> (<i>Sci</i>WS) in a <i>S. cerevisiae</i> strain, overexpressing a range of other enzymes involved in FA synthesis and elongation, leads to a yeast strain capable of producing high amounts of monounsaturated FOHs (up to C22:1-FOH) as well as diunsaturated WEs (up to C46:2-WE).<strong>Conclusions: </strong>Changing the FA profile of the yeast <i>S. cerevisiae</i> towards very long-chain monounsaturated FAs is possible by combined overexpression of endogenous and heterologous enzymes derived from various sources (e.g. a marine copepod or plants). This strategy was used to produce jojoba-like WEs in <i>S. cerevisiae</i> and can potentially be extended towards other commercially interesting products derived from very long-chain FAs.

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44

Sturtevant, Drew, Shaoping Lu, Zhi-Wei Zhou, et al. "The genome of jojoba (Simmondsia chinensis): A taxonomically isolated species that directs wax ester accumulation in its seeds." Science Advances 6, no. 11 (2020): eaay3240. http://dx.doi.org/10.1126/sciadv.aay3240.

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Seeds of the desert shrub, jojoba (Simmondsia chinensis), are an abundant, renewable source of liquid wax esters, which are valued additives in cosmetic products and industrial lubricants. Jojoba is relegated to its own taxonomic family, and there is little genetic information available to elucidate its phylogeny. Here, we report the high-quality, 887-Mb genome of jojoba assembled into 26 chromosomes with 23,490 protein-coding genes. The jojoba genome has only the whole-genome triplication (γ) shared among eudicots and no recent duplications. These genomic resources coupled with extensive transcriptome, proteome, and lipidome data helped to define heterogeneous pathways and machinery for lipid synthesis and storage, provided missing evolutionary history information for this taxonomically segregated dioecious plant species, and will support efforts to improve the agronomic properties of jojoba.

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45

Mat Radzi, Salina, Mahiran Basri, Abu Bakar Salleh, et al. "Optimisation study of large-scale enzymatic synthesis of oleyl oleate, a liquid wax ester, by response surface methodology." Journal of Chemical Technology & Biotechnology 81, no. 3 (2006): 374–80. http://dx.doi.org/10.1002/jctb.1404.

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46

Phan, Mai Thi Tuyet, Boi Van Luu та Lan Ngoc Pham. "Synthesis and elaboration of modified comb type (maleic anhydride-α-tetradecene) copolymers for cold flow improvers of biodiesel". Ministry of Science and Technology, Vietnam 63, № 2 (2021): 13–19. http://dx.doi.org/10.31276/vjste.63(2).13-19.

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The maleic anhydride-α-tetradecene copolymer (OMAC) with an approximate relative maleic anhydride to α-tetradecene composition ratio of 1:1.2 was synthesized by free radical copolymerization. The copolymers were modified by the esterification reaction between the anhydride groups and the OH- group of hexadecanol. Comb-type (-maleic acid cetyl ester-co-α-tetradecene-) copolymers (MCEC) with various ratios of alkyl group/carboxyl group (r) were investigated. Upon cooling, the MCEC changed the crystallization state of the wax crystals, and reduced the pour point of the biodiesel, which was observed by pour point and dynamic viscosity testing. The MCEC efficiency that improved the cold flow properties of the biodiesel was found to be correlated to r. MCEC with r=2.76 was found to be the most effective in improving the flow ability of the palm oil biodiesel. Our study demonstrates the ability of MCEC3 at 1000 ppm concentration to reduce the pour point of palm oil biodiesel to 10.5oC and the dynamic viscosity up to 1.04 mPa.s. A correlation was found between the number and the length of the pendant alkyl groups of additives and the compositions of the fatty acid methyl ester of the biodiesel.

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47

Al-Arafi, Naowara M., and Jumat Salimon. "Synthesis of Long Chain Wax Ester, using the Bronsted Acidic Ionic Liquid N-Methyl-2-Pyrrolidonium Methyl Sulphate ([NMP][CH3SO3])." Research Journal of Applied Sciences 6, no. 6 (2011): 361–65. http://dx.doi.org/10.3923/rjasci.2011.361.365.

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48

Hoffmeister, Meike, Markus Piotrowski, Ulrich Nowitzki, and William Martin. "Mitochondrialtrans-2-Enoyl-CoA Reductase of Wax Ester Fermentation fromEuglena gracilisDefines a New Family of Enzymes Involved in Lipid Synthesis." Journal of Biological Chemistry 280, no. 6 (2004): 4329–38. http://dx.doi.org/10.1074/jbc.m411010200.

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49

Lima, Letícia C. D., Daniela G. C. Peres, and Adriano A. Mendes. "Kinetic and thermodynamic studies on the enzymatic synthesis of wax ester catalyzed by lipase immobilized on glutaraldehyde-activated rice husk particles." Bioprocess and Biosystems Engineering 41, no. 7 (2018): 991–1002. http://dx.doi.org/10.1007/s00449-018-1929-9.

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50

Yang, Yunqiang, Yanan Pu, Xin Yin, et al. "A Splice Variant of BrrWSD1 in Turnip (Brassica rapa var. rapa) and Its Possible Role in Wax Ester Synthesis under Drought Stress." Journal of Agricultural and Food Chemistry 67, no. 40 (2019): 11077–88. http://dx.doi.org/10.1021/acs.jafc.9b04069.

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