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焦谷氨酰 - 肽键的水解裂解。III. 在70%甲磺酸中的高度选择性裂解

Hydrolytic cleavage of pyroglutamyl-peptide bond. III. A highly selective cleavage in 70% methanesulfonic acid.

作者信息

Hashimoto T, Ohki K, Sakura N

机构信息

Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa, Japan.

出版信息

Chem Pharm Bull (Tokyo). 1996 Nov;44(11):2033-6. doi: 10.1248/cpb.44.2033.

DOI:10.1248/cpb.44.2033
PMID:8945768
Abstract

A method for highly selective cleavage of pGlu-peptide linkages in 70% methanesulfonic acid (MSA) is described. When pGlu-Ala-Phe-OH, pGlu-His-Pro-Oh and dog neuromedin U-8 (d-NMU-8) (1--7)-OH (pGlu-Phe-Leu-Phe-Arg-OH) were hydrolyzed in 70% MSA at 60 degrees C for 3 h or at 25 degrees C for 3 d, the pGlu-peptide linkage was predominantly cleaved to give H-Ala-OH, H-His-Pro-OH and H-Phe-Leu-Phe-Arg-Pro-Arg-OH, in high yields. The results indicated that pGlu-peptide linkages are highly susceptible to 70% MSA, whereas the amide bond of the pyrrolidone moiety of the pGlu residue and other internal peptide bonds are extremely resistant.

摘要

本文描述了一种在70%甲磺酸(MSA)中高度选择性裂解焦谷氨酸 - 肽键的方法。当焦谷氨酸 - 丙氨酸 - 苯丙氨酸 - 羟基(pGlu - Ala - Phe - OH)、焦谷氨酸 - 组氨酸 - 脯氨酸 - 羟基(pGlu - His - Pro - Oh)和狗神经介素U - 8(d - NMU - 8)(1 - 7)- 羟基(pGlu - Phe - Leu - Phe - Arg - OH)在70% MSA中于60℃水解3小时或在25℃水解3天时,焦谷氨酸 - 肽键主要被裂解,分别高产率地得到H - Ala - OH、H - His - Pro - OH和H - Phe - Leu - Phe - Arg - Pro - Arg - OH。结果表明,焦谷氨酸 - 肽键对70% MSA高度敏感,而焦谷氨酸残基吡咯烷酮部分的酰胺键和其他内部肽键则极具抗性。

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