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Journal articles on the topic 'Thioester synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Kerdraon, Florent, Gemma Bogard, Benoît Snella, et al. "Insights into the Mechanism and Catalysis of Peptide Thioester Synthesis by Alkylselenols Provide a New Tool for Chemical Protein Synthesis." Molecules 26, no. 5 (2021): 1386. http://dx.doi.org/10.3390/molecules26051386.

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While thiol-based catalysts are widely employed for chemical protein synthesis relying on peptide thioester chemistry, this is less true for selenol-based catalysts whose development is in its infancy. In this study, we compared different selenols derived from the selenocysteamine scaffold for their capacity to promote thiol–thioester exchanges in water at mildly acidic pH and the production of peptide thioesters from bis(2-sulfanylethyl)amido (SEA) peptides. The usefulness of a selected selenol compound is illustrated by the total synthesis of a biologically active human chemotactic protein,

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2

Komiya, Chiaki, Akira Shigenaga, Jun Tsukimoto, et al. "Traceless synthesis of protein thioesters using enzyme-mediated hydrazinolysis and subsequent self-editing of the cysteinyl prolyl sequence." Chemical Communications 55, no. 49 (2019): 7029–32. http://dx.doi.org/10.1039/c9cc03583d.

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3

Siebert, David C. B., Roman Sommer, Domen Pogorevc, et al. "Chemical synthesis of tripeptide thioesters for the biotechnological incorporation into the myxobacterial secondary metabolite argyrin via mutasynthesis." Beilstein Journal of Organic Chemistry 15 (December 5, 2019): 2922–29. http://dx.doi.org/10.3762/bjoc.15.286.

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The argyrins are secondary metabolites from myxobacteria with antibiotic activity against Pseudomonas aeruginosa. Studying their structure–activity relationship is hampered by the complexity of the chemical total synthesis. Mutasynthesis is a promising approach where simpler and fully synthetic intermediates of the natural product’s biosynthesis can be biotechnologically incorporated. Here, we report the synthesis of a series of tripeptide thioesters as mutasynthons containing the native sequence with a dehydroalanine (Dha) Michael acceptor attached to a sarcosine (Sar) and derivatives. Chemic

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4

Murli, Sumati, Karen S. MacMillan, Zhihao Hu, et al. "Chemobiosynthesis of Novel 6-Deoxyerythronolide B Analogues by Mutation of the Loading Module of 6-Deoxyerythronolide B Synthase 1." Applied and Environmental Microbiology 71, no. 8 (2005): 4503–9. http://dx.doi.org/10.1128/aem.71.8.4503-4509.2005.

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ABSTRACT Chemobiosynthesis (J. R. Jacobsen, C. R. Hutchinson, D. E. Cane, and C. Khosla, Science 277:367-369, 1997) is an important route for the production of polyketide analogues and has been used extensively for the production of analogues of 6-deoxyerythronolide B (6-dEB). Here we describe a new route for chemobiosynthesis using a version of 6-deoxyerythronolide B synthase (DEBS) that lacks the loading module. When the engineered DEBS was expressed in both Escherichia coli and Streptomyces coelicolor and fed a variety of acyl-thioesters, several novel 15-R-6-dEB analogues were produced. Th

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5

Coleman, Tricia M., and Faqing Huang. "RNA-Catalyzed Thioester Synthesis." Chemistry & Biology 9, no. 11 (2002): 1227–36. http://dx.doi.org/10.1016/s1074-5521(02)00264-8.

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6

Macmillan, Derek, and Durbis Castillo-Pazos. "Investigation of Cysteine as an Activator of Side-Chain N→S Acyl Transfer and Tail-to-Side-Chain Cyclization." Synlett 28, no. 15 (2017): 1923–28. http://dx.doi.org/10.1055/s-0036-1590797.

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N→S Acyl transfer is a popular method for the postsynthesis production of peptide C α-thioesters for use in native chemical ligation and for the synthesis of head-to-tail cyclic peptides. Meanwhile thioester formation at the side chain of aspartic or glutamic acids, leading to tail-to-side-chain-cyclized species, is less common. Herein we explore the potential for cysteine to function as a latent thioester when appended to the side chain of glutamic acid. Initial insights gained through study of C-terminal β-alanine as a model for the increased chain length were ultimately applied to peptide m

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7

Hahn, Frank, Nadine Kandziora, Steffen Friedrich, and Peter Francis Leadlay. "Synthesis of complex intermediates for the study of a dehydratase from borrelidin biosynthesis." Beilstein Journal of Organic Chemistry 10 (March 11, 2014): 634–40. http://dx.doi.org/10.3762/bjoc.10.55.

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Herein, we describe the syntheses of a complex biosynthesis-intermediate analogue of the potent antitumor polyketide borrelidin and of reference molecules to determine the stereoselectivity of the dehydratase of borrelidin polyketide synthase module 3. The target molecules were obtained from a common precursor aldehyde in the form of N-acetylcysteamine (SNAc) thioesters and methyl esters in 13 to 15 steps. Key steps for the assembly of the polyketide backbone of the dehydratase substrate analogue were a Yamamoto asymmetric carbocyclisation and a Sakurai allylation as well as an anti-selective

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8

Rauch, Michael, Jie Luo, Liat Avram, Yehoshoa Ben-David, and David Milstein. "Mechanistic Investigations of Ruthenium Catalyzed Dehydrogenative Thioester Synthesis and Thioester Hydrogenation." ACS Catalysis 11, no. 5 (2021): 2795–807. http://dx.doi.org/10.1021/acscatal.1c00418.

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9

Fila, Karolina, Beata Podkościelna, and Maciej Podgórski. "Cross-Linked Polythiomethacrylate Esters Based on Naphthalene—Synthesis, Properties and Reprocessing." Materials 13, no. 13 (2020): 3021. http://dx.doi.org/10.3390/ma13133021.

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Two structurally different aromatic dithioesters were synthesized from two dithiols and methacryloyl chloride. The polymer networks based on methyl methacrylate and/or styrene and the new dimethacrylates were subsequently prepared. The polymerization yields of copolymers were in the range of 95–99%. The thermal and mechanical properties of the copolymers were determined by means of differential scanning calorimetry (DSC), thermogravimetric analysis (TG/DTG), and Shore D hardness. The addition of dithioesters—1,5-NAF-S-Met (or 1,4(1,5)-NAF-CH2S-Met) (from 0.5% to 5%) to MMA- or ST-based polymer

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10

Aimoto, Saburo. "Polypeptide synthesis by the thioester method." Biopolymers 51, no. 4 (1999): 247–65. http://dx.doi.org/10.1002/(sici)1097-0282(1999)51:4<247::aid-bip2>3.0.co;2-w.

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11

Ling, Jingjing J., Rocco L. Policarpo, Amy E. Rabideau, Xiaoli Liao, and Bradley L. Pentelute. "Protein Thioester Synthesis Enabled by Sortase." Journal of the American Chemical Society 134, no. 26 (2012): 10749–52. http://dx.doi.org/10.1021/ja302354v.

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12

Semler, Ursula, Gunter Schmidtberg, and Georg G. Gross. "Synthesis of Piperoyl Coenzyme A Thioester." Zeitschrift für Naturforschung C 42, no. 9-10 (1987): 1070–74. http://dx.doi.org/10.1515/znc-1987-9-1011.

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Piperoyl-CoA, a potential intermediate in the biosynthesis of piperine. the pungent principle of pepper, was synthesized via N-succinimidyl piperate and subsequent transesterification with CoA- SH. UV-spectrophotometry of the HPLC-purified compound revealed, besides a maximum at 260 nm, a pronounced second absorption maximum at 368 nm due to the thioester linkage for which, as determined via the Fe3+-complex of piperoyl hydroxamate and with [14C]piperoyl-CoA, a molar extinction coefficient of 30.8 × 106 [cn2mol-1] was calculated.

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13

Olson, Andrew S., Haotong Chen, Liangcheng Du, and Patrick H. Dussault. "Synthesis of a 2,4,6,8,10-dodecapentanoic acid thioester as a substrate for biosynthesis of heat stable antifungal factor (HSAF)." RSC Advances 5, no. 15 (2015): 11644–48. http://dx.doi.org/10.1039/c4ra14829k.

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14

Tsuda, Shugo, Taku Yoshiya, Tsuyoshi Uemura, Masayoshi Mochizuki, and Hideki Nishio. "Preparation of Peptide o-Aminoanilides Using a Modified Dawson's Linker for Microwave-Assisted Peptide Synthesis." Synlett 28, no. 15 (2017): 1956–60. http://dx.doi.org/10.1055/s-0036-1588862.

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Based on the structure of Dawson’s 3,4-diaminobenzoic acid (Dbz) linker designed for Fmoc solid-phase peptide-thioester synthesis, the 4-amino-3-nitrobenzoic acid [Dbz(NO2)] linker was developed for microwave-assisted synthesis. The Dbz(NO2) linker can be readily converted into the Dbz linker by on-resin reduction with SnCl2 after construction of the protected peptide resin. Although epimerization of C-terminal amino acid restricts the use of Dbz(NO2) linker to the synthesis of peptide-Gly-thioester, use of this linker can prevent side reactions that arise when Dbz or Dbz(Aloc) linkers are use

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15

Akagawa, Kengo, and Kazuaki Kudo. "Biomimetic iterative method for polyketide synthesis." Chemical Communications 53, no. 62 (2017): 8645–48. http://dx.doi.org/10.1039/c7cc04033d.

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An iterative method for synthesizing polyketides was demonstrated, in which the chain elongation of a carboxylic acid was performed by decarboxylative dehydration condensation with a malonic acid half thioester.

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16

Frenzel, Thomas, Marco Brünjes, Monika Quitschalle, and Andreas Kirschning. "Synthesis of theN-Acetylcysteamine Thioester ofseco-Proansamitocin." Organic Letters 8, no. 1 (2006): 135–38. http://dx.doi.org/10.1021/ol052588q.

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17

Tsuda, Shugo, Shun Masuda, and Taku Yoshiya. "The versatile use of solubilizing trityl tags for difficult peptide/protein synthesis." Organic & Biomolecular Chemistry 17, no. 5 (2019): 1202–5. http://dx.doi.org/10.1039/c8ob03098g.

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18

Hajra, Saumen, Suhas Shivajirao Bhosale, and Atanu Hazra. "An asymmetric acetate-Mannich reaction of chiral isatin derived ketimines and its applications." Organic & Biomolecular Chemistry 15, no. 43 (2017): 9217–25. http://dx.doi.org/10.1039/c7ob02407j.

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A highly efficient TMSOTf-mediated asymmetric acetate-Mannich reaction of chiral isatin derived ketimines and S-phenyl thioacetate was developed to afford the direct synthesis of indole-based β<sup>3,3</sup>-amino acid thioester with excellent selectivity (dr > 98 : 2). Syntheses of (+)-AG-041R and 3-aminopyrroloindoline have been accomplished utilizing the method.

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19

Linder, David, and Rainer Schobert. "Synthesis of the fungus metabolite cladosin C." Organic & Biomolecular Chemistry 15, no. 36 (2017): 7672–77. http://dx.doi.org/10.1039/c7ob01795b.

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Cladosin C was built up in ten steps comprising an N-acylation of dehydrovaline with a functionalised thioester, a Dieckmann cylisation, and an OH ⇒ NH<sub>2</sub> exchange with 2,4-dimethoxybenzylamine.

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20

Yanase, Masafumi, Koki Nakatsu, Charlane Joy Cardos, Yoshiki Konda, Gosuke Hayashi, and Akimitsu Okamoto. "Cysteinylprolyl imide (CPI) peptide: a highly reactive and easily accessible crypto-thioester for chemical protein synthesis." Chemical Science 10, no. 23 (2019): 5967–75. http://dx.doi.org/10.1039/c9sc00646j.

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21

Terrier, Victor P., Hélène Adihou, Mathieu Arnould, Agnès F. Delmas, and Vincent Aucagne. "A straightforward method for automated Fmoc-based synthesis of bio-inspired peptide crypto-thioesters." Chemical Science 7, no. 1 (2016): 339–45. http://dx.doi.org/10.1039/c5sc02630j.

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22

Boll, Emmanuelle, Hervé Drobecq, Nathalie Ollivier, et al. "A novel PEG-based solid support enables the synthesis of >50 amino-acid peptide thioesters and the total synthesis of a functional SUMO-1 peptide conjugate." Chem. Sci. 5, no. 5 (2014): 2017–22. http://dx.doi.org/10.1039/c3sc53509f.

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23

Liu, Lingzhi, Libin Wu, Junyan Tan, et al. "“Reduction” responsive thymine-conjugated biodynamers: synthesis and solution properties." Polymer Chemistry 6, no. 21 (2015): 3934–41. http://dx.doi.org/10.1039/c5py00200a.

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Nucleobase-conjugated biodynamers are generated by RAFT polymerization and the transthioesterification reaction. The biodynamers containing thioester linkages demonstrate GSH-responsive feature, and can interact with melamine and ATP in water.

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24

Aimoto, Saburo. "ChemInform Abstract: Polypeptide Synthesis by the Thioester Method." ChemInform 31, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.200024264.

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25

Helinck, Sandra, Henry E. Spinnler, Sandrine Parayre, MichÃ¨le Dame-Cahagne, and Pascal Bonnarme. "Enzymatic versus spontaneousS-methyl thioester synthesis inGeotrichum candidum." FEMS Microbiology Letters 193, no. 2 (2000): 237–41. http://dx.doi.org/10.1111/j.1574-6968.2000.tb09430.x.

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26

Weber, Arthur L. "Oligoglyceric acid synthesis by autocondensation of glyceroyl thioester." Journal of Molecular Evolution 25, no. 3 (1987): 191–96. http://dx.doi.org/10.1007/bf02100011.

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27

Cao, Yuan, Giang K. T. Nguyen, James P. Tam, and Chuan-Fa Liu. "Butelase-mediated synthesis of protein thioesters and its application for tandem chemoenzymatic ligation." Chemical Communications 51, no. 97 (2015): 17289–92. http://dx.doi.org/10.1039/c5cc07227a.

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28

Pira, S. L., O. El Mahdi, L. Raibaut, et al. "Insight into the SEA amide thioester equilibrium. Application to the synthesis of thioesters at neutral pH." Organic & Biomolecular Chemistry 14, no. 30 (2016): 7211–16. http://dx.doi.org/10.1039/c6ob01079b.

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29

Izumi, Masayuki, Shinji Komaki, Ryo Okamoto, et al. "Synthesis of misfolded glycoprotein dimers through native chemical ligation of a dimeric peptide thioester." Organic & Biomolecular Chemistry 14, no. 25 (2016): 6088–94. http://dx.doi.org/10.1039/c6ob00928j.

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30

Cronan, John E. "The chain-flipping mechanism of ACP (acyl carrier protein)-dependent enzymes appears universal." Biochemical Journal 460, no. 2 (2014): 157–63. http://dx.doi.org/10.1042/bj20140239.

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ACPs (acyl carrier proteins) play essential roles in the synthesis of fatty acids, polyketides and non-ribosomal polypeptides. ACP function requires the modification of the protein by attachment of 4′-phosphopantetheine to a conserved serine residue. The phosphopantetheine thiol acts to tether the starting materials and intermediates as their thioesters. ACPs are small highly soluble proteins composed of four α-helices. The helices form a bundle that acts as a hydrophobic sleeve that sequesters the acyl chains and activated thioesters from solvent. However, in the synthesis of fatty acids and

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31

Torkko, Juha M., Kari T. Koivuranta, Ilkka J. Miinalainen, et al. "Candida tropicalis Etr1p andSaccharomyces cerevisiae Ybr026p (Mrf1′p), 2-Enoyl Thioester Reductases Essential for Mitochondrial Respiratory Competence." Molecular and Cellular Biology 21, no. 18 (2001): 6243–53. http://dx.doi.org/10.1128/mcb.21.18.6243-6253.2001.

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ABSTRACT We report here on the identification and characterization of novel 2-enoyl thioester reductases of fatty acid metabolism, Etr1p fromCandida tropicalis and its homolog Ybr026p (Mrf1′p) fromSaccharomyces cerevisiae. Overexpression of these proteins in S. cerevisiae led to the development of significantly enlarged mitochondria, whereas deletion of the S. cerevisiae YBR026c gene resulted in rudimentary mitochondria with decreased contents of cytochromes and a respiration-deficient phenotype. Immunolocalization and in vivo targeting experiments showed these proteins to be predominantly mit

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32

Islam, Sk Manirul, Rostam Ali Molla, Anupam Singha Roy, and Kajari Ghosh. "Polymer supported Pd catalyzed thioester synthesis via carbonylation of aryl halides under phosphine free conditions." RSC Adv. 4, no. 50 (2014): 26181–92. http://dx.doi.org/10.1039/c4ra03338h.

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A new polymer anchored Pd(ii) complex has been synthesized and characterized. The catalytic performance of this complex has been tested for thioester synthesis via carbonylation of aryl halides and thiols under phosphine free conditions. This catalyst showed excellent catalytic activity and recyclability.

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33

Liao, Yen-Sen, and Chien-Fu Liang. "One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions." Organic & Biomolecular Chemistry 16, no. 11 (2018): 1871–81. http://dx.doi.org/10.1039/c8ob00178b.

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34

Vandenbergh, Joke, Gijs Ramakers, Luk van Lokeren, Guy van Assche, and Thomas Junkers. "Synthesis of degradable multi-segmented polymers via Michael-addition thiol–ene step-growth polymerization." RSC Advances 5, no. 100 (2015): 81920–32. http://dx.doi.org/10.1039/c5ra18861j.

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Degradable multi-segmented poly(β-thioester) linear polymers and networks are synthesized via step-growth thiol–ene polymerization of diacrylates with telechelic dithiol polystyrene and poly(isobornylacrylate) precursor polymers.

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35

Baumruck, A. C., D. Tietze, L. K. Steinacker, and A. A. Tietze. "Chemical synthesis of membrane proteins: a model study on the influenza virus B proton channel." Chemical Science 9, no. 8 (2018): 2365–75. http://dx.doi.org/10.1039/c8sc00004b.

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36

Jios, Jorge L., Srecko I. Kirin, Thomas Weyhermüller, Nils Metzler-Nolte, and Carlos O. Della Védova. "Synthesis, structural and spectroscopic study of aromatic thioester compounds." Journal of Molecular Structure 825, no. 1-3 (2006): 53–59. http://dx.doi.org/10.1016/j.molstruc.2006.04.013.

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37

Zheng, Ji-Shen, Shan Tang, Yi-Chao Huang, and Lei Liu. "Development of New Thioester Equivalents for Protein Chemical Synthesis." Accounts of Chemical Research 46, no. 11 (2013): 2475–84. http://dx.doi.org/10.1021/ar400012w.

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38

Kawakami, Toru, Koki Hasegawa, and Saburo Aimoto. "Synthesis of a Phosphorylated Polypeptide by a Thioester Method." Bulletin of the Chemical Society of Japan 73, no. 1 (2000): 197–203. http://dx.doi.org/10.1246/bcsj.73.197.

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39

Manabe, Shino, Tomoyuki Sugioka, and Yukishige Ito. "Facile peptide thioester synthesis via solution-phase tosylamide preparation." Tetrahedron Letters 48, no. 5 (2007): 849–53. http://dx.doi.org/10.1016/j.tetlet.2006.11.143.

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40

Hemu, Xinya, Misako Taichi, Yibo Qiu, Ding-Xiang Liu, and James P. Tam. "Biomimetic synthesis of cyclic peptides using novel thioester surrogates." Biopolymers 100, no. 5 (2013): 492–501. http://dx.doi.org/10.1002/bip.22308.

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41

Erlich, Lesly A., K. S. Ajish Kumar, Mahmood Haj-Yahya, Philip E. Dawson, and Ashraf Brik. "N-Methylcysteine-mediated total chemical synthesis of ubiquitin thioester." Organic & Biomolecular Chemistry 8, no. 10 (2010): 2392. http://dx.doi.org/10.1039/c000332h.

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42

Mangroo, Dev, and Gerhard E. Gerber. "Synthesis of acyl-CoA thioesters." Biochemistry and Cell Biology 68, no. 1 (1990): 308–12. http://dx.doi.org/10.1139/o90-042.

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An improved synthesis of fatty acyl coenzyme A has been developed that permits the synthesis of highly radioactive fatty acyl coenzyme A derivatives and thus can be used for the synthesis of high specific activity photoaffinity labels. Conditions were developed to solubilize the coenzyme A in anhydrous solvent for the acylation. The complete activation of fatty acid to the imidazolide is described and the acylation of the coenzyme A under anhydrous conditions was shown to result in the conversion of the fatty acid to the fatty acyl coenzyme A derivative. The synthetic product was shown by its

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43

Sharma, Mahendra Kumar, Soumen Sinhababu, Pritam Mahawar, et al. "Donor–acceptor-stabilised germanium analogues of acid chloride, ester, and acyl pyrrole compounds: synthesis and reactivity." Chemical Science 10, no. 16 (2019): 4402–11. http://dx.doi.org/10.1039/c8sc05380d.

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Hitherto unknown germaacid chloride (1), germaester (2), and Ngermaacyl pyrrole (3) compounds are stabilised as Lewis acid complexes. Reactivity studies on them yielded compounds such as germaynone (4) and germaacyl thioester (10).

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44

Devaraj, Neal K., and Charles L. Perrin. "Approach control. Stereoelectronic origin of geometric constraints on N-to-S and N-to-O acyl shifts in peptides." Chemical Science 9, no. 7 (2018): 1789–94. http://dx.doi.org/10.1039/c7sc04046f.

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Intramolecular N-to-S or N-to-O acyl shifts in peptides are of fundamental and practical importance, as they constitute the first step in protein splicing and can be used for the synthesis of thioester-modified peptides required for native chemical ligation.

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45

Du, Yijun, Yanyan Xu, Chenze Qi, and Chen Wang. "Mechanistic study on the Knorr pyrazole synthesis-thioester generation reaction." Tetrahedron Letters 60, no. 30 (2019): 1999–2004. http://dx.doi.org/10.1016/j.tetlet.2019.06.053.

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46

Simion, Cristian, Iwao Hashimoto, Yoshiharu Mitoma, Alina Marieta Simion, and Naoyoshi Egashira. "Rapid and Convenient Thioester Synthesis Under Phase-Transfer Catalysis Conditions." Phosphorus, Sulfur, and Silicon and the Related Elements 185, no. 12 (2010): 2480–88. http://dx.doi.org/10.1080/10426501003713072.

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47

Kang, Jaskiranjit, and Derek Macmillan. "Peptide and protein thioester synthesis via N→S acyl transfer." Organic & Biomolecular Chemistry 8, no. 9 (2010): 1993. http://dx.doi.org/10.1039/b925075a.

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48

Kolarovic, Andrej, Alexander Käslin, and Helma Wennemers. "Stereoselective Synthesis of Indolines via Organocatalytic Thioester Enolate Addition Reactions." Organic Letters 16, no. 16 (2014): 4236–39. http://dx.doi.org/10.1021/ol501936n.

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49

Kanda, Yutaka, Tadashi Ashizawa, Shingo Kakita, et al. "Synthesis and Antitumor Activity of Novel Thioester Derivatives of Leinamycin." Journal of Medicinal Chemistry 42, no. 8 (1999): 1330–32. http://dx.doi.org/10.1021/jm9900366.

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50

Zheng, Ji-Shen, Shan Tang, Yun-Kun Qi, Zhi-Peng Wang, and Lei Liu. "Chemical synthesis of proteins using peptide hydrazides as thioester surrogates." Nature Protocols 8, no. 12 (2013): 2483–95. http://dx.doi.org/10.1038/nprot.2013.152.

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