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胰岛素A链中A_(6-11)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A_(6-7)+A_(8-11)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)。
The A 6-11 hexapeptide derivative of insulin A chain, Cbz (S-Bz) Cys · (S-Bz) Cys · Ala · Gly · Val · (S-Bz) Cys OEt Diimine method and mixed anhydride method according to A_ (6-7) + A_ (8-11) pathway were synthesized. This article reports the synthesis of the same compound by the azidation method, and avoids the side reaction of amides produced by the previous synthesis of this peptide using the same method, and significantly improves the yield. 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) and Cbz · (S-Bz) Cys · Gly · Ala · Gly · Val · (S-Bz) Cys OEt Satisfactory results. Dipeptide esters (H Val · (S-Bz) Cys · OEt or H Val · (S-Bz) Cys · OBz) are easily cyclized cyclically by heating or in solution for a long time to form the same L-form 3-benzyl Sulfomethyl-6-isopropyl-2,5-dioxohexahydropyrazine (III).