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Application of Pac Ester in thioester method for the Synthesis of Cyclopentapeptides

Chinese Journal of Chemistry 2003年第7期21卷 864-870页

作者：刘勉田桂玲叶蕴华 Key Laboratory of Bioorganic Chemistry and Molecular Engineering Ministry of EducationDepartment of ChemistryPeking University Beijing 100871 China

thioester method for the synthesis of cyclopeptides is improved by using Pac (Pac = phenacyl, CH2COC6H5) ester as a protecting group of 3-mercaptopropionic acid. The Pac group is easy to be removed from C-terminal with zinc in acetic acid. The protected glycine thioester and peptide thioesters synthesized by the unproved method, are easy to be purified, so the final linear peptides are pure enough for the following cyclization. Furthermore, this method is flexible for peptide chain elongation, either from C-terminal or from N-terminal. So it is an efficient and practical method for synthesis of bioactive peptides. Two N-protected pentapeptide thioesters, Boc-Pro-Tyr-Leu-Ala-GlySCH2CH2COOPac and Boc-Ala-Tyr-Leu-Ala-Gly-SCH2CH2-COOPac were synthesized by the improved thioester method. After deprotecting Pac ester with zinc in aqueous acetic acid and Boc group with trifluoroacetic acid in CH2C12, two free pentapeptide thioesters were obtained. Ag+ -assisted cyclization in acetate buffered solution afforded two cyclic pentapeptides c(Pro-Tyr-Leu-Ala-Gly) and c(Ala-Tyr-Leu-Ala-Gly). Effects of different buffer pH, different Ag+ concentrations, etc. on the cyclization were studied.

关键词： thioester method Pac ester cyclopentapeptide

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Improvement of thioester method by Using Pac Ester for Synthesis of Cyclopentapeptides

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Chinese Chemical Letters 2002年第11期13卷 1059-1060页

作者： MianLIU GuiLingTIAN 等 TheKeyLaboratoryofBioorganicChemistryandMolecularEngineering MinistryofEducationCollegeofChemistryandMolecularEngineeringPekingUniversityBeijing100871 TheKeyLaboratoryofBioorganicChemistryandMolecul

thioester method was improved by using Pac (phenacyl group) ester as protecting group of 3-mercaptopropionic acid. Two cyclopentapeptides c(Ala-Tyr-Leu-Ala-Gly) and c(Pro-Tyr-Leu- Ala-Gly) were synthesized successful... 详细信息

关键词： thioester method Pac ester cyclopentapeptide.

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Recent Progress of thioester method

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Chemical Research in Chinese Universities 2006年第2期22卷 253-257页

作者： Saburo Aimoto Kenta Teruya Koki Hasegawa Takeshi Sato Kenichi Akaji Toru Kawakami Institute for Protein Research Osaka University Suita Osaka 565-0871 Japan

Introduction The availability of site-specifically modified peptides is of vital importance for biochemical and biophysical studies. Biological methods, such as expression using bacteria, are useful. They are, however, not always applicable to the synthesis of peptides with sitespecific modifications. Chemical methods can be viable alternatives to those biological approaches. Peptides obtained by chemical and biological means,

关键词： thioester method Thiol linker Peptide

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