REACTION-MECHANISMS IN PEPTIDE-SYNTHESIS .1. SEMIQUANTITATIVE CHARACTERISTICS OF THE REACTIVITY OF 2-METHYL-5(4H)-OXAZOLONE WITH WATER AND AMMONIA IN THE GAS-PHASE AND WEAKLY POLAR MEDIA

被引：6

作者：

CIARKOWSKI, J ^{[1
]}

CHEN, FMF ^{[1
]}

BENOITON, NL ^{[1
]}

机构：

[1] UNIV OTTAWA,FAC MED,DEPT BIOCHEM,OTTAWA K1H 8M5,ONTARIO,CANADA

来源：

JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN | 1991年 / 5卷 / 06期

关键词：

AM1; MOPAC; N-ACETYLGLYCINE AMIDE; ALPHA-HYDROXYIMINE; TAUTOMERISM;

D O I：

10.1007/BF00135316

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

2,4-Dialkyl-5(4H)-oxazolones are well-recognized intermediates in some aminolysis reactions in peptide synthesis. Using the MOPAC molecular orbital programs, detailed geometric and energetic characteristics of the elementary reaction pathways for the additions of water and ammonia to 2-methyl-5(4H)-oxazolone have been determined at the AM1 level. The results demonstrate that the additions must be parsed into a two-step mechanism involving formation of the alpha-hydroxyimine followed by tautomerization to the parent N-acetylamino acid or amide.

引用

页码：585 / 597

页数：13

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