GENERATION OF ALPHA-ACETOXYGLYCINE RESIDUES WITHIN PEPTIDE CHAINS - A NEW STRATEGY FOR THE MODIFICATION OF OLIGOPEPTIDES

被引：48

作者：

APITZ, G ^{[1
]}

JAGER, M ^{[1
]}

JAROCH, S ^{[1
]}

KRATZEL, M ^{[1
]}

SCHAFFELER, L ^{[1
]}

STEGLICH, W ^{[1
]}

机构：

[1] UNIV MUNICH,INST ORGAN CHEM,KARLSTR 23,W-8000 MUNICH 2,GERMANY

来源：

TETRAHEDRON | 1993年 / 49卷 / 36期

关键词：

D O I：

10.1016/S0040-4020(01)88040-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Seryl and threonyl peptides are converted into alpha-acetoxyglycyl peptides by treatment with lead tetraacetate. Reaction of these acetoxy derivatives or the more reactive alpha-chloroglycyl peptides with thiols, dithiols and carbohydrates allows the attachment of such units to peptide chains. The reaction of alpha-chloroglycyl peptides with amino acid esters and enamines proceeds with high stereoselectivity and yields peptides with N,N-acetal and (2-oxocyclohexyl)glycine moieties, respectively.

引用

页码：8223 / 8232

页数：10

共 29 条

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