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Relevant bibliographies by topics / Thioester synthesis

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Academic literature on the topic 'Thioester synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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Journal articles on the topic "Thioester synthesis"

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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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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Dissertations / Theses on the topic "Thioester synthesis"

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Le, Sann Christine. "Enantioselective synthesis of N-Acetylcysteamine thioester putative intermediates to polyketides." Thesis, University of Bristol, 2001. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.340274.

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2

Torkko, J. (Juha). "Characterization of mitochondrial 2-enoyl thioester reductase involved in respiratory competence." Doctoral thesis, University of Oulu, 2003. http://urn.fi/urn:isbn:9514270312.

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Abstract Maintenance of the mitochondrial respiratory chain complexes plays crucial role for the aerobic metabolism of the eukaryotes such as unicellular yeasts, for example, Saccharomyces cerevisiae as well as of human being. Mitochondrial respiratory function has been studied using the yeast S. cerevisiae as a model organism. Since yeast cells are also able to grow without respiration by fermentation, identification of the nuclear genes linked to respiratory function is possible by generation of nuclear gene deletions and testing for respiration-deficient phenotype of the yeast deletion str

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3

Miinalainen, I. (Ilkka). "Enoyl thioester reductases—enzymes of fatty acid synthesis and degradation in mitochondria." Doctoral thesis, University of Oulu, 2006. http://urn.fi/urn:isbn:9514282442.

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Abstract Fatty acids are one of the most essential categories of biological lipids and their synthesis and degradation are vital for all organisms. Severely compromised phenotypes of yeast mutants and human patients, which have defective components in their degradative or synthetic processes for fatty acid metabolism, have highlighted the importance of these processes for overall metabolism. Most fatty acids are degraded by β-oxidation, which occurs in mitochondria and peroxisomes in mammals, whereas synthesis is catalyzed by cytosolic multifunctional peptides, although a synthesis system invo

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4

Soares-Sello, Anna Mampe. "Biosynthetic studies of strobilurins." Thesis, University of Bristol, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.389145.

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5

Brandes, Dee Anne. "The synthesis and reactivity of alpha,beta-unsaturated thioamide, thioester, and thione iron tricarbonyl complexes." Thesis, University of Ottawa (Canada), 1990. http://hdl.handle.net/10393/6008.

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$\alpha,\beta$-Unsaturated thioamide, thioester and thione iron tricarbonyl complexes 1-13 were prepared from the free ligands and iron pentacarbonyl using photolysis or diiron nonacarbonyl using thermolysis. X-ray crystal structures were obtained for the free ligand 2$\sp\prime,$ (PhCH=C(Ph)C(S)NEt$\sb2$), and for complexes 1 and 2, $\rm\lbrack \overline{\overline{Fe(PhCH}{=}CHC(S})NEt\sb2)$(CO)$\sb3\rbrack$ and $\rm\lbrack \overline{\overline{Fe(PhCH}{=}C(Ph)C(S})NEt\sb2)$(CO)$\sb3\rbrack$ respectively. Thioamide and thioester iron tricarbonyl complexes gave triphenylphosphine substituted co

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6

Chen, Z. (Zhijun). "Characterization of the 2-enoyl thioester reductase of mitochondrial fatty acid synthesis type II in mammals." Doctoral thesis, University of Oulu, 2008. http://urn.fi/urn:isbn:9789514289804.

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Abstract A data base search using the amino acid sequence of Saccharomyces cerevisiae Etr1p, the last enzyme of mitochondrial fatty acid synthesis type II (FAS II), revealed a highly similar human protein, NRBF-1. Expression of NRBF-1 in a yeast etr1Δ strain rescued its respiratory deficiency. NRBF-1 resides in mitochondria in cultured HeLa cells. The recombinant NRBF-1 is enzymatically active, reducing 2E-enoyl-CoAs to acyl-CoAs in an NADPH-dependent manner. Altogether, our data showed that NRBF-1 is a mitochondrial 2-enoyl-CoA reductase/2-enoyl thioester reductase (MECR/ETR1), the human fun

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7

Sutherland, Ian Thor. "APPLYING A LATE-STAGE LAWESSON’S CYCLIZATION STRATEGY TOWARDS THE SYNTHESIS OF 1,3,4-THIADIAZOLE-2-CARBOXYLATE THIOESTERS." Kent State University Honors College / OhioLINK, 2015. http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1437100137.

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8

Henze, Rüdiger. "Tautomérisation énantiosélective d'un énol." Rouen, 1997. http://www.theses.fr/1997ROUES020.

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La réaction de l'aldéhyde 2-benzylacrylique avec des acides thiocarboxyliques donne accès à de nouveaux énols métastables. Leur conformation a été étudiée en utilisant des calculs semi-empiriques et des méthodes spectroscopiques. Des calculs AM1 ont révélé que la conformation préférée du Z-éthanethioate de 2-benzyl-3-hydroxy-2-propényle en absence de solvants fait intervenir une interaction intramoléculaire entre les groupements hydroxyle et carbonyle du thioester. Une étude par IR et par RMN a montré que la conformation du Z-1-benzènecarbothioate de 2-benzyl-3-hydroxy-2-propényle était dépend

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9

Turkarslan, Ozlem. "Synthesis, Characterization And Electrochromic Properties Of Conducting Copolymers Of Terephthalic Acid Bis-(thiophen-3-ylmethyl)thioester With Thiophene And Pyrrole And Conducting Polymer Of 1-(4-fluorophenyl)-2,5-di(thiophen-2-yl)-1h-pyrrole." Master's thesis, METU, 2006. http://etd.lib.metu.edu.tr/upload/12607169/index.pdf.

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Terephthalic acid bis-(thiophen-3-ylmethyl)thioester (TTMT) was synthesized via the reaction of thiophen-3-ylmethanethiol with terephthaloyl dichloride. Nuclear magnetic resonance (1H-NMR) and Fourier transform infrared (FTIR) spectroscopies were utilized for the characterization of the monomer. This 3-functionalized thiophene monomer was polymerized in the presence of thiophene (Th) and pyrrole (Py) upon constant potential application in acetonitrile/tetrabutylammonium tetrafluoroborate (TBAFB). The resulting copolymers were characterized via cyclic voltammetry (CV), FTIR, differential scanni

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10

Shah, Syed Tasadaque Ali. "Regio- und stereoselektive Synthesen von chiralen heterozyklischen Kohlenhydratkonjugaten Cäsiumfluorid-Celit: eine feste Base für die Synthese von Estern, Ethern, Thioestern, Thioethern und symmetrischen Disulfiden /." [S.l. : s.n.], 2003. http://www.bsz-bw.de/cgi-bin/xvms.cgi?SWB10733078.

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Books on the topic "Thioester synthesis"

1

United States. National Aeronautics and Space Administration, ed. Oligoglyceric acid synthesis by autocondensation of glyceroyl thioester. National Aeronautics and Space Administration, 1986.

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Book chapters on the topic "Thioester synthesis"

1

Hojo, Hironobu. "Chemical Synthesis of Glycoproteins by the Thioester Method." In Chemical Ligation. John Wiley & Sons, Inc., 2017. http://dx.doi.org/10.1002/9781119044116.ch6.

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2

Kawakami, Toru. "Peptide Thioester Formation via an Intramolecular N to S Acyl Shift for Peptide Ligation." In Protein Ligation and Total Synthesis I. Springer International Publishing, 2014. http://dx.doi.org/10.1007/128_2014_575.

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3

Wang, Yu, and Yi-Ming Li. "Peptide Hydrazides as Thioester Equivalents for the Chemical Synthesis of Proteins." In Expressed Protein Ligation. Springer US, 2020. http://dx.doi.org/10.1007/978-1-0716-0434-2_6.

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4

Kawakami, Toru, Koki Hasegawa, Kenta Teruya, et al. "Synthesis of Phosphorylated Polypeptide by the Thioester Method Using a Recombinant Protein." In Peptides: The Wave of the Future. Springer Netherlands, 2001. http://dx.doi.org/10.1007/978-94-010-0464-0_71.

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5

Ni, Qiang, and Luping Yu. "Synthesis of Thioester End-Functionalized Poly(ε-caprolactone) and Its Application in Chemoselective Ligation." In ACS Symposium Series. American Chemical Society, 1998. http://dx.doi.org/10.1021/bk-1998-0709.ch006.

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6

Hojo, Hironobu, Yuko Onuma, Yuri Akimoto, Yuko Nakahara, and Yoshiaki Nakahara. "A Novel Method for the Preparation of Peptide Thioester and its Application to Glycoprotein Synthesis." In Advances in Experimental Medicine and Biology. Springer New York, 2009. http://dx.doi.org/10.1007/978-0-387-73657-0_57.

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7

Palà-Pujadas, Judith, and Juan B. Blanco-Canosa. "Native Chemical Ligation via N-Acylurea Thioester Surrogates Obtained by Fmoc Solid-Phase Peptide Synthesis." In Expressed Protein Ligation. Springer US, 2020. http://dx.doi.org/10.1007/978-1-0716-0434-2_7.

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8

Lelièvre, Dominique, and George Barany. "Backbone Amide Linker (BAL)/Fmoc Synthesis of Peptide Thioester Intermediates Required for Native Chemical Ligation." In Peptides: The Wave of the Future. Springer Netherlands, 2001. http://dx.doi.org/10.1007/978-94-010-0464-0_100.

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9

Aimoto, Saburo, Kenta Teruya, Koki Hasegawa, Kenichi Akaji, and Toru Kawakami. "The Use of a Free Peptide for Preparation of a C-Terminal Building Block for Polypeptide Synthesis in Combination with a Peptide Thioester." In Peptides: The Wave of the Future. Springer Netherlands, 2001. http://dx.doi.org/10.1007/978-94-010-0464-0_49.

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Raz, Richard, and John Offer. "A Shortcut to the Synthesis of Peptide Thioesters." In Methods in Molecular Biology. Springer US, 2020. http://dx.doi.org/10.1007/978-1-0716-0928-6_1.

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Conference papers on the topic "Thioester synthesis"

1

Fox, Robert O., and Kris F. Tesh. "PAET Resin for the Synthesis of Peptide Thioesters." In The Twenty-Third American and the Sixth International Peptide Symposium. Prompt Scientific Publishing, 2013. http://dx.doi.org/10.17952/23aps.2013.228.

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2

Gouvêa, Venise A., José C. Campos, Juliano Bosenbecker, et al. "Synthesis of amides and thioesteres derivatives, precursors to heterocyclic thiazolidinones." In 14th Brazilian Meeting on Organic Synthesis. Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0052-1.

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Sakamoto, Ken, Kohei Sato, Akira Shigenaga, Daisuke Tsuji, Kohji Itoh, and Akira Otaka. "Development of Efficient Synthetic Method for N-Amino Acyl N-Sulfanylethyl Anilide Linkers as Peptide Thioester Equivalent." In The Twenty-Third American and the Sixth International Peptide Symposium. Prompt Scientific Publishing, 2013. http://dx.doi.org/10.17952/23aps.2013.242.

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