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化学学报
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化学学报 ›› 1965, Vol. 31 ›› Issue (6): 509-513. 上一篇    下一篇

含半胱氨酸多肽的研究——Ⅱ.胰岛素A鏈中小环部份(A6-A11)合成方法的改进及其类似物的合成

陸德培, 李崇熙, 邢其毅   

  1. 北京大学化学系
  • 投稿日期:1964-12-20 发布日期:2013-06-03

CYSTEINE PEPTIDES Ⅱ. AN IMPROVED SYNTHESIS OF PROTECTED HEXAPEPTIDE WITH THE AMINO ACID SEQUENCE 6—11 OF THE A-CHAIN OF INSULIN AND ITS ANALOGUES

LOH TEH-PEI, LI CHUNG-HSI, HSING CHI-YI   

  1. Department of Chemistry, Peking University
  • Received:1964-12-20 Published:2013-06-03

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胰岛素A链中A6-11六肽衍生物,Cbz(S-Bz)Cys·(S-Bz)Cys·Ala·Gly·Val·(S-Bz)Cys OEt(Ⅱ),曾用碳二亚胺法和混合酸酐法依A6-7+A8-11途径分别合成。本文报告用迭氮法合成同一化合物,且避免前人用同法合成这一肽段时产生酰胺的副反应,并明显提高产率。用同样方法又合成与(Ⅱ)同型的六肽,Cbz·(S-Bz)Cys·Ala·Ala·Gly·Val·(S-Bz)Cys OEt(Ⅷ),Cbz(S-Bz)·Cys·Leu·Ala·Gly·Val·(S-Bz)·Cys OEt(Ⅸ)和Cbz·(S-Bz)Cys·Gly·Ala·Gly·Val·(S-Bz)Cys OEt(Ⅹ),均得满意结果。二肽酯(H Val·(S-Bz)Cys·OEt或H Val·(S-Bz)Cys·OBz)经长期放置或在溶液中加热易于自行环化而形成同一的L-型3-苄硫甲基-6-异丙基-2,5-二氧代六氢吡嗪(Ⅲ)。

Carbobenzyloxy (S-benzyl)cyteinyl (S-benzyl) cysteinylalanylglycylvalyl (S-benzyl) cysteinyl ethyl ester (Ⅱ), a derivative of the hexapeptide fragment (A6-11) of A-Chain of insulin, had been prepared by coupling alanylglycylvalyl(S-benzyl)cysteinyl ethyl ester with carbo-benryloxy(S-benzyl)cysteinyl(S-benryl)cysteine by the carbodiimide or the mixed anhydride methods respectively. This paper reports that the same peptide can also be prepared by the azide method, but with much better yield and without the formation of the amide. Using the same method we have also prepared three other analogous hexapeptides, namely, carbobenryloxy (S-benryl) cysteinyl-alanylalanylglycylvalyl (S-benzyl) cysteinyl ethyl ester (Ⅷ), carbobenzyloxy(S-benzyl)cysteinylleucylalanylglycylvalyl (S-benryl) cysteinyl ethyl ester (Ⅸ), and carbobenryloxy(S-benryl)cysteinylglycylalanylglycylvalyl(S-benzyl)cysteinyl ethyl ester (Ⅹ) with excellent results.