The hydrolysis of primary amide groups in Asn/Gln-containing peptides

被引：0

作者：

Onoprienko, VV ^{[1
]}

Yelin, EA ^{[1
]}

Miroshnikov, AI ^{[1
]}

机构：

[1] Russian Acad Sci, Shemyakin Ovchinnikov Inst Bioorgan Chem, Moscow 117871, Russia

来源：

BIOORGANICHESKAYA KHIMIYA | 2000年 / 26卷 / 06期

关键词：

asparagine; aspartic acid; glutamine; glutamic acid; peptides; epimerization; primary amides; selective saponification; rearrangement;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

Peptides Boc-Ala-Asn/Gln-OH and Boc-Asn/Gln-Ala-OH were saponified with barium hydroxide to corresponding Asp/Glu-containing peptides. Under the conditions of saponification, Boc-Asn-Ala-OH additionally afforded Boc-Asp-OH, isopeptide Boc-Asp(Ala)-OH, and Boc-NHSuc > Ala-OH, with the third being the key intermediate in these transformations. Boc-Asp(OMe)-Ala-OMe underwent similar transformations under treatment with diazomethane or triethylamine. Saponification with barium hydroxide was accompanied by a high epimerization of N-terminal amino acid residues, whereas the products of the diazomethane treatment of Boc-Asp(OMe)-Ala-OMe had a low degree of epimerization.

引用

页码：403 / 410

页数：8

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