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Journal articles on the topic 'Enzymatic acylation'

Author: Grafiati
Published: 4 June 2021
Last updated: 11 March 2023

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1

MURUI, Tateo, Hiroaki TSUJI, and Yuri ARAI. "Enzymatic Acylation of Sterylglycosides." Journal of Japan Oil Chemists' Society 44, no. 3 (1995): 211–14. http://dx.doi.org/10.5650/jos1956.44.211.

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2

Chebil, Latifa, Catherine Humeau, Aude Falcimaigne, Jean-Marc Engasser, and Mohamed Ghoul. "Enzymatic acylation of flavonoids." Process Biochemistry 41, no. 11 (November 2006): 2237–51. http://dx.doi.org/10.1016/j.procbio.2006.05.027.

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3

Alissandratos, Apostolos, and Peter J. Halling. "Enzymatic acylation of starch." Bioresource Technology 115 (July 2012): 41–47. http://dx.doi.org/10.1016/j.biortech.2011.11.030.

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4

BAÑÓ, M. Carmen, S. Caroline JACKSON, and I. Anthony MAGEE. "Pseudo-enzymatic S-acylation of a myristoylated Yes protein tyrosine kinase peptide in vitro may reflect non-enzymatic S-acylation in vivo." Biochemical Journal 330, no. 2 (March 1, 1998): 723–31. http://dx.doi.org/10.1042/bj3300723.

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Covalent attachment of a variety of lipid groups to proteins is now recognized as a major group of post-translational modifications. S-acylation of proteins at cysteine residues is the only modification considered dynamic and thus has the potential for regulating protein function and/or localization. The activities that catalyse reversible S-acylation have not been well characterized and it is not clear whether both the acylation and the deacylation steps are regulated, since in principle it would be sufficient to control only one of them. Both apparently enzymatic and non-enzymatic S-acylation of proteins have previously been reported. Here we show that a synthetic myristoylated c-Yes protein tyrosine kinase undecapeptide undergoes spontaneous S-acylation in vitro when using a long chain acyl-CoA as acyl donor in the absence of any protein. The S-acylation was dependent on myristoylation of the substrate, the length of the incubation period, temperature and substrate concentration. When COS cell fractions were added to the S-acylation reaction no additional peptide:S-acyltransferase activity was detected. These results are consistent with the possibility that membrane-associated proteins may undergo S-acylation in vivo by non-enzymatic transfer of acyl groups from acyl-CoA. In this case, the S-acylation-deacylation process could be controlled by a regulated depalmitoylation mechanism.
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5

Intra, Annalisa, Adriana Bava, Gianluca Nasini, and Sergio Riva. "Regioselective enzymatic acylation of polyhydroxylated sesquiterpenoids." Journal of Molecular Catalysis B: Enzymatic 29, no. 1-6 (June 2004): 95–98. http://dx.doi.org/10.1016/j.molcatb.2003.10.009.

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6

Simerská, Pavla, Andrea Pišvejcová, Marek Kuzma, Petr Sedmera, Vladimı́r Křen, Silvia Nicotra, and Sergio Riva. "Regioselective enzymatic acylation of N-acetylhexosamines." Journal of Molecular Catalysis B: Enzymatic 29, no. 1-6 (June 2004): 219–25. http://dx.doi.org/10.1016/j.molcatb.2003.10.018.

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7

Nicotra, F., S. Riva, F. Secundo, and L. Zucchelli. "ω-Functionalized Esters by Enzymatic Acylation." Synthetic Communications 20, no. 5 (March 1990): 679–85. http://dx.doi.org/10.1080/00397919008052310.

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8

Gonzalo, Gonzalo de, Iván Lavandera, Rosario Brieva, and Vicente Gotor. "Enzymatic acylation reactions on ω-hydroxycyanohydrins." Tetrahedron 60, no. 46 (November 2004): 10525–32. http://dx.doi.org/10.1016/j.tet.2004.06.134.

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9

Roychoudhury, S., R. E. Kaiser, D. N. Brems, and W. K. Yeh. "Specific interaction between beta-lactams and soluble penicillin-binding protein 2a from methicillin-resistant Staphylococcus aureus: development of a chromogenic assay." Antimicrobial Agents and Chemotherapy 40, no. 9 (September 1996): 2075–79. http://dx.doi.org/10.1128/aac.40.9.2075.

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We investigated the enzymatic acylation of penicillin-binding protein 2a (PBP 2a) from methicillin-resistant Staphylococcus aureus by beta-lactams. Using a purified, soluble form of the protein (PBP 2a'), we observed beta-lactam-induced in vitro precipitation following first-order kinetics with respect to protein concentration. We used electrospray mass ionization spectrometry to show that the protein precipitate predominantly contained PBP 2a', with the beta-lactam bound to it in a 1:1 molar ratio. Using nitrocefin, a chromogenic beta-lactam, we confirmed the correlation between PBP 2a' precipitation and its beta-lactam-dependent enzymatic acylation by monitoring the absorbance associated with the precipitate. Finally, dissolving the precipitate in urea, we developed a simple in vitro chromogenic assay to monitor beta-lactam-dependent enzymatic acylation of PBP 2a'. This assay represents a significant improvement over the traditional radioactive penicillin-binding assay.
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10

Lee, Donghyun, Kyung-Chul Kim, and Mahn-Joo Kim. "Selective enzymatic acylation of 10-Deacetylbaccatin III." Tetrahedron Letters 39, no. 49 (December 1998): 9039–42. http://dx.doi.org/10.1016/s0040-4039(98)02049-8.

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11

Lay, Luigi, Luigi Panza, Sergio Riva, Malika Khitri, and Salvatore Tirendi. "Regioselective acylation of disaccharides by enzymatic transesterification." Carbohydrate Research 291 (September 1996): 197–204. http://dx.doi.org/10.1016/s0008-6215(96)00157-7.

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12

Lay, L. "Regioselective acylation of disaccharides by enzymatic transesterification." Carbohydrate Research 291, no. 1 (September 23, 1996): 127–39. http://dx.doi.org/10.1016/0008-6215(96)00157-7.

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13

Zhu, Song, Baoshuang Du, Dejian Huang, Yongmei Xia, Shangwei Chen, and Yue Li. "Highly Efficient Regioselective Acylation of Dihydromyricetin Catalyzed by Lipase in Nonaqueous Solvents." Processes 10, no. 7 (July 13, 2022): 1368. http://dx.doi.org/10.3390/pr10071368.

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This study aimed to explore the enzymatic acylation of dihydromyricetin (DHM) to synthesized DHM derivatives with a different substituted carbon chain to improve its liposolubility. In the presence of Lipozyme TL IM, DHM was butyrylated in a 96.28% conversion in methyl tert-butyl ether under the optimized conditions (molar ratio of DHM to vinyl butyrate, 1:20; lipase dosage, 0.4 U/mg DHM; temperature, 50 °C; stirrer speed, 200 rpm; reaction time, 72 h). Liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR) spectroscopy revealed that two acylation products were formed; these were 7-O-acyl-DHM and 3-O-acyl-DHM. In addition, the liposolubility of the DHM derivatives increased with the increase in the substituted carbon chain length; their antioxidant activities were higher than that of DHM in the lecithin peroxidation system, and C8-DHM had a better effect. Therefore, enzymatic acylation broadens the application of DHM in a lipid system in the food field.
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14

Chamberlain, Luke H., and Michael J. Shipston. "The Physiology of Protein S-acylation." Physiological Reviews 95, no. 2 (April 2015): 341–76. http://dx.doi.org/10.1152/physrev.00032.2014.

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Protein S-acylation, the only fully reversible posttranslational lipid modification of proteins, is emerging as a ubiquitous mechanism to control the properties and function of a diverse array of proteins and consequently physiological processes. S-acylation results from the enzymatic addition of long-chain lipids, most typically palmitate, onto intracellular cysteine residues of soluble and transmembrane proteins via a labile thioester linkage. Addition of lipid results in increases in protein hydrophobicity that can impact on protein structure, assembly, maturation, trafficking, and function. The recent explosion in global S-acylation (palmitoyl) proteomic profiling as a result of improved biochemical tools to assay S-acylation, in conjunction with the recent identification of enzymes that control protein S-acylation and de-acylation, has opened a new vista into the physiological function of S-acylation. This review introduces key features of S-acylation and tools to interrogate this process, and highlights the eclectic array of proteins regulated including membrane receptors, ion channels and transporters, enzymes and kinases, signaling adapters and chaperones, cell adhesion, and structural proteins. We highlight recent findings correlating disruption of S-acylation to pathophysiology and disease and discuss some of the major challenges and opportunities in this rapidly expanding field.
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15

Sereti, V., H. Stamatis, E. Koukios, and F. N. Kolisis. "Enzymatic acylation of cellulose acetate in organic media." Journal of Biotechnology 66, no. 2-3 (December 1998): 219–23. http://dx.doi.org/10.1016/s0168-1656(98)00085-6.

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16

Sergeev, Maxim E., and Tatiana L. Voyushina. "Enzymatic acylation of nucleosides—Novel route to nucleopeptides." Journal of Molecular Catalysis B: Enzymatic 62, no. 1 (January 2010): 104–6. http://dx.doi.org/10.1016/j.molcatb.2009.09.006.

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17

Cruz Silva, M. Manuel, Sergio Riva, and M. Luisa Sá e Melo. "Regioselective enzymatic acylation of vicinal diols of steroids." Tetrahedron 61, no. 12 (March 2005): 3065–73. http://dx.doi.org/10.1016/j.tet.2005.01.104.

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18

Gill, Iqbal I., Jagbandhu Das, and Ramesh N. Patel. "Enantioselective enzymatic acylation of 1-(3′-bromophenyl)ethylamine." Tetrahedron: Asymmetry 18, no. 11 (June 2007): 1330–37. http://dx.doi.org/10.1016/j.tetasy.2007.05.039.

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19

Pérez, José Andrés, Juan Manuel Trujillo, Hermelo López, Zulma Aragón, and Carlos Boluda. "Regioselective Enzymatic Acylation and Deacetylation of Secoiridoid Glucosides." CHEMICAL & PHARMACEUTICAL BULLETIN 57, no. 8 (2009): 882–84. http://dx.doi.org/10.1248/cpb.57.882.

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20

Dąbkowska, Katarzyna, and Krzysztof W. Szewczyk. "Kinetics of enantioselective enzymatic acylation of mandelic acid." Journal of Biotechnology 131, no. 2 (September 2007): S79—S80. http://dx.doi.org/10.1016/j.jbiotec.2007.07.139.

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21

Xiao, Yong Mei, Pu Mao, Zhen Zhao, Liang Ru Yang, and Xian Fu Lin. "Regioselective enzymatic acylation of troxerutin in nonaqueous medium." Chinese Chemical Letters 21, no. 1 (January 2010): 59–62. http://dx.doi.org/10.1016/j.cclet.2009.08.017.

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22

Hilgers, Roelant, Jean-Paul Vincken, and Mirjam A. Kabel. "Facile enzymatic Cγ-acylation of lignin model compounds." Catalysis Communications 136 (March 2020): 105919. http://dx.doi.org/10.1016/j.catcom.2019.105919.

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23

Chua, Lee-Suan, and Mohamad Roji Sarmidi. "Enzymatic Enantioselective Acylation of Sterically Aromatic Secondary Alcohol." Developments in Chemical Engineering and Mineral Processing 13, no. 5-6 (May 15, 2008): 605–16. http://dx.doi.org/10.1002/apj.5500130510.

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24

Iribarren, Adolfo M., and Luis E. Iglesias. "An update of biocatalytic selective acylation and deacylation of monosaccharides." RSC Advances 6, no. 20 (2016): 16358–86. http://dx.doi.org/10.1039/c5ra23453k.

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PAMs synthesis requires highly selective reactions, provided by hydrolases. This review updates research on enzymatic acylation and deacylation of monosaccharides, focusing on synthetic useful PAMs and drug-monosaccharide conjugates involving PAMs.
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25

Li, Xiufang, Ceng Zhang, Lingshuang Wang, Caili Ma, Weichao Yang, and Mingzhong Li. "Acylation Modification ofAntheraea pernyiSilk Fibroin Using Succinic Anhydride and Its Effects on Enzymatic Degradation Behavior." Journal of Chemistry 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/640913.

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The degradation rate of tissue engineering scaffolds should match the regeneration rate of new tissues. Controlling the degradation behavior of silk fibroin is an important subject for silk-based tissue engineering scaffolds. In this study,Antheraea pernyisilk fibroin was successfully modified with succinic anhydride and then characterized by zeta potential, ninhydrin method, and FTIR.In vitro, three-dimensional scaffolds prepared with modified silk fibroin were incubated in collagenase IA solution for 18 days to evaluate the impact of acylation on the degradation behavior. The results demonstrated that the degradation rate of modified silk fibroin scaffolds was more rapid than unmodified ones. The content of theβ-sheet structure in silk fibroin obviously decreased after acylation, resulting in a high degradation rate. Above all, the degradation behavior of silk fibroin scaffolds could be regulated by acylation to match the requirements of various tissues regeneration.
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26

LIAU, Y. H., J. ZIELENSKI, S. R. CARTER, A. SLOMIANY, and B. L. SLOMIANY. "Enzymatic Acylation of Mucus Glycoprotein in Rat Salivary Glands." Annals of the New York Academy of Sciences 494, no. 1 Third Colloqu (May 1987): 345–47. http://dx.doi.org/10.1111/j.1749-6632.1987.tb29568.x.

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27

Galletti, Paola, Fabio Moretti, Chiara Samorì, and Emilio Tagliavini. "Enzymatic acylation of levoglucosan in acetonitrile and ionic liquids." Green Chemistry 9, no. 9 (2007): 987. http://dx.doi.org/10.1039/b702031g.

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28

Djeghaba, Zeineddine, Hervé Deleuze, Bernard De Jeso, Djeloul Messadi, and Bernard Maillard. "Enzymes in organic synthesis VII: enzymatic acylation of amines." Tetrahedron Letters 32, no. 6 (February 1991): 761–62. http://dx.doi.org/10.1016/s0040-4039(00)74878-7.

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29

Xu, Qing, Yongli Xie, Xiaohong Geng, and Peiran Chen. "Enzymatic kinetic resolution of racemic cyanohydrins via enantioselective acylation." Tetrahedron 66, no. 3 (January 2010): 624–30. http://dx.doi.org/10.1016/j.tet.2009.11.074.

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30

Berger, B., C. G. Rabiller, K. Königsberger, K. Faber, and H. Griengl. "Enzymatic acylation using acid anhydrides: Crucial removal of acid." Tetrahedron: Asymmetry 1, no. 8 (January 1990): 541–46. http://dx.doi.org/10.1016/s0957-4166(00)80545-5.

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31

Chen, Zhi-Gang, Min-Hua Zong, Zhen-Xin Gu, and Yong-Bin Han. "Effect of ultrasound on enzymatic acylation of konjac glucomannan." Bioprocess and Biosystems Engineering 31, no. 4 (October 26, 2007): 351–56. http://dx.doi.org/10.1007/s00449-007-0171-7.

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32

Khmelnitsky, Yuri L., Cheryl Budde, J. Michael Arnold, Alexander Usyatinsky, Douglas S. Clark, and Jonathan S. Dordick. "Synthesis of Water-Soluble Paclitaxel Derivatives by Enzymatic Acylation." Journal of the American Chemical Society 119, no. 47 (November 1997): 11554–55. http://dx.doi.org/10.1021/ja973103z.

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33

Paravidino, Monica, and Ulf Hanefeld. "Enzymatic acylation: assessing the greenness of different acyl donors." Green Chemistry 13, no. 10 (2011): 2651. http://dx.doi.org/10.1039/c1gc15576h.

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34

Heba, Monika, Anna Wolny, Anna Kastelik-Hryniewiecka, Dominika Stradomska, Sebastian Jurczyk, Anna Chrobok, and Nikodem Kuźnik. "Green Dynamic Kinetic Resolution—Stereoselective Acylation of Secondary Alcohols by Enzyme-Assisted Ruthenium Complexes." Catalysts 12, no. 11 (November 9, 2022): 1395. http://dx.doi.org/10.3390/catal12111395.

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Dynamic kinetic resolution allows for the synthesis of enantiomerically pure asymmetric alcohols. Cyclopentadienyl-derived ruthenium catalysts were immobilized with an ionic liquid, [BMIM][NTf2], on multiwall carbon nanotubes and used for the racemization of chiral secondary alcohols. This successful approach was combined with the enantioselective enzymatic acylation of secondary alcohols (1-phenylethanol and 1-(1-naphthyl)ethanol) using Novozyme® 435. The resulting catalytic system of the ruthenium racemization catalysts and enzymatic acylation led to chiral esters being obtained by dynamic kinetic resolution. The immobilized catalytic system in the ionic liquid gave the same activity of >96% yield within 6 h and a selectivity of 99% enantiomeric excess as the homogeneous system, while allowing for the convenient separation of the desired products from the catalyst. Additionally, the process can be regarded as green, since the efficient reuse of the catalytic system was demonstrated.
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35

Porfyris, Athanasios, Constantine D. Papaspyrides, Natnael Behabtu, Cristian Lenges, and Alexander Kopatsis. "High-Solids, Solvent-Free Modification of Engineered Polysaccharides." Molecules 26, no. 13 (July 2, 2021): 4058. http://dx.doi.org/10.3390/molecules26134058.

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The nature-identical engineered polysaccharide α-(1,3) glucan, produced by the enzymatic polymerization of sucrose, was chemically modified by acylation with succinic anhydride. This modification reaction was initially performed at the micro scale in a TGA reactor to access a range of reaction conditions and to study the mechanism of the reaction. Subsequently, the best performing conditions were reproduced at the larger laboratory scale. The reaction products were characterized via coupled TGA/DSC analysis, FT-IR spectroscopy, solution viscosity and pH determination. The acylation path resulted in partially modifying the polysaccharide by altering its behavior in terms of thermal properties and solubility. The acylation in a solvent-free approach was found promising for the development of novel, potentially melt-processable and fully bio-based and biodegradable ester compounds.
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36

Miyazawa, Toshifumi, Manabu Hamada, and Ryohei Morimoto. "Candida antarctica lipase B-catalyzed regioselective deacylation of dihydroxybenzenes acylated at both phenolic hydroxy groups." Canadian Journal of Chemistry 94, no. 1 (January 2016): 44–49. http://dx.doi.org/10.1139/cjc-2015-0335.

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Candida antarctica lipase B proved to be highly active in the deacylation of substituted hydroquinones and resorcinols acylated at both phenolic hydroxy groups. The deacylation reactions were much faster than the corresponding direct acylations of these dihydroxybenzenes catalyzed by the same lipase. More importantly, they took place generally in a markedly regioselective manner: the acyloxy group remote from the substituent was preferentially cleaved. The main or exclusive products obtained were the regioisomers of those produced through the direct acylation of the dihydroxybenzenes. In the case of alkyl-substituted hydroquinone derivatives, the regioselectivity increased with an increase in the bulk of the substituent. In the case of 4-substituted diacylated resorcinols, the 3-O-monoacyl derivatives were obtained generally as the sole products. Quite interestingly, some secondary alcohols proved to act as better acyl acceptors than the corresponding primary alcohols in these enzymatic deacylations.
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37

Du, Li-Hua, Jia-Hong Shen, Zhen Dong, Na-Ni Zhou, Bing-Zhuo Cheng, Zhi-Min Ou, and Xi-Ping Luo. "Enzymatic synthesis of nucleoside analogues from uridines and vinyl esters in a continuous-flow microreactor." RSC Advances 8, no. 23 (2018): 12614–18. http://dx.doi.org/10.1039/c8ra01030g.

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We achieved the effective controllable regioselective acylation of the primary hydroxyl group of uridine derivatives catalyzed by Lipase TL IM from Thermomyces lanuginosus with excellent conversion and regioselectivity.
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38

Pulido, Rosalino, Fernando L�pez Ortiz, and Vicente Gotor. "Enzymatic regioselective acylation of hexoses and pentoses using oxime esters." Journal of the Chemical Society, Perkin Transactions 1, no. 21 (1992): 2891. http://dx.doi.org/10.1039/p19920002891.

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39

Ulijn, Rein V., Nicola Bisek, and Sabine L. Flitsch. "Enzymatic optical resolution via acylation–hydrolysis on a solid support." Organic & Biomolecular Chemistry 1, no. 4 (January 28, 2003): 621–22. http://dx.doi.org/10.1039/b211887d.

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40

RIVA, SERGIO, GIACOMO CARREA, GIANLUCA OTTOLINA, FRANCESCO SECUNDO, BRUNO DANIELI, and PAOLO BELLIS. "Enzymatic Regioselective Acylation of Polyhydroxylated Natural Compounds in Organic Solvents." Annals of the New York Academy of Sciences 613, no. 1 Enzyme Engine (December 1990): 712–16. http://dx.doi.org/10.1111/j.1749-6632.1990.tb18251.x.

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41

Menéndez, Emma, and Vicente Gotor. "Acylation and Alkoxycarbonylation of Oximes Through an Enzymatic Oximolysis Reaction." Synthesis 1993, no. 01 (1993): 72–74. http://dx.doi.org/10.1055/s-1993-25798.

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42

Hong, Shin Yee, Li Theng Ng, Li Fang Ng, Takao Inoue, Nicholas S. Tolwinski, Thilo Hagen, and Jan Gruber. "The Role of Mitochondrial Non-Enzymatic Protein Acylation in Ageing." PLOS ONE 11, no. 12 (December 29, 2016): e0168752. http://dx.doi.org/10.1371/journal.pone.0168752.

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43

MARTINS, M., J. JORGE, and M. CRUZ. "Acylation of l-asparaginase with total retention of enzymatic activity." Biochimie 72, no. 9 (September 1990): 671–75. http://dx.doi.org/10.1016/0300-9084(90)90050-q.

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44

Panza, Luigi, Monica Luisetti, Emanuela Crociati, and Sergio Riva. "Selective Acylation of 4,6-O-Benzylidene Glycopyranosides by Enzymatic Catalysis." Journal of Carbohydrate Chemistry 12, no. 1 (January 1993): 125–30. http://dx.doi.org/10.1080/07328309308018546.

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45

González-Sabín, Javier, Roberto Morán-Ramallal, and Francisca Rebolledo. "Regioselective enzymatic acylation of complex natural products: expanding molecular diversity." Chemical Society Reviews 40, no. 11 (2011): 5321. http://dx.doi.org/10.1039/c1cs15081b.

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46

Liu, Bo-Kai, Na Wang, Qi Wu, Chuan-Ying Xie, and Xian-Fu Lin. "Regioselective enzymatic acylation of ribavirin to give potential multifunctional derivatives." Biotechnology Letters 27, no. 10 (May 2005): 717–20. http://dx.doi.org/10.1007/s10529-005-5188-x.

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47

Park, Hyun Gyu, Jin Hwan Do, and Ho Nam Chang. "Regioselective enzymatic acylation of multi-hydroxyl compounds in organic synthesis." Biotechnology and Bioprocess Engineering 8, no. 1 (February 2003): 1–8. http://dx.doi.org/10.1007/bf02932891.

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48

Gremos, Stavros, Dimitra Zarafeta, Dimitris Kekos, and Fragiskos Kolisis. "Direct enzymatic acylation of cellulose pretreated in BMIMCl ionic liquid." Bioresource Technology 102, no. 2 (January 2011): 1378–82. http://dx.doi.org/10.1016/j.biortech.2010.09.021.

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49

Kulkarni, Rhushikesh A., Andrew J. Worth, Thomas T. Zengeya, Jonathan H. Shrimp, Julie M. Garlick, Allison M. Roberts, David C. Montgomery, et al. "Discovering Targets of Non-enzymatic Acylation by Thioester Reactivity Profiling." Cell Chemical Biology 24, no. 2 (February 2017): 231–42. http://dx.doi.org/10.1016/j.chembiol.2017.01.002.

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50

DJEGHABA, Z., H. DELEUZE, B. MAILLARD, and B. DE JESO. "ChemInform Abstract: Enzymatic Pathway for the Regioselective Acylation of Spermidine." ChemInform 26, no. 31 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199531105.

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