| Application of Pac Ester in Thioester Method for the Synthesis of Cyclopentapeptides |
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| 作者姓名： | 刘勉 田桂玲 叶蕴华 |
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| 作者单位： | KeyLaboratoryofBioorganicChemistryandMolecularEngineering,MinistryofEducation,DepartmentofChemistry,PekingUniversity,Belting100871,China |
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| 基金项目： | Project supported by the National Natural Science Foundation of China(No.29772001). |
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| 摘 要： | Thioester method for the synthesis of cyclopeptides is improved by using Pac (Pac = phenacyl, CH2COC6Hs) 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 improved 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-termlnal 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-GIySCH2CH2COOPac and Boc-Ala-Tyr-Leu-Ala-Gly-SCH2CH2COOPac were synthesized by the improved thloester method.After deprotecting Pac ester with zinc in aqueous acetic acid and Boc group with trifluoroacetic acid in CH2C12, two free pentapeptide tldoesters 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.
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| 关 键 词： | 苯甲酰甲基酯 硫酯 制备 环戊二烯肽 天然化合物 液相合成 |
Application of Pac Ester in Thioester Method for the Synthesis of Cyclopentapeptides |
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| LIU,Mian TIAN,Gui-Ling YE,Yun-Hua
Key Laboratory of Bioorganic Chemistry and Molecular Engineering,Ministry of Education.Application of Pac Ester in Thioester Method for the Synthesis of Cyclopentapeptides[J].Chinese Journal of Chemistry,2003,21(7):864-870. |
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| Authors: | LIU Mian TIAN Gui-Ling YE Yun-Hua
Key Laboratory of Bioorganic Chemistry and Molecular Engineering Ministry of Education |
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| Institution: | LIU,Mian TIAN,Gui-Ling YE,Yun-Hua
Key Laboratory of Bioorganic Chemistry and Molecular Engineering,Ministry of Education,Department of Chemistry,Peking University,Beijing 100871,China |
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| Abstract: | 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. |
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| Keywords: | thioester method Pac ester cyclopentapeptide |
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