Constrained Glu-Gly and Gln-Gly dipeptide surrogates from γ-substituted α-amino-δ-lactam synthesis

被引：2

作者：

Mulamreddy, Ramakotaiah ^{[1
]}

Lubell, William D. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, POB 6128,Stn Ctr Ville, Montreal, PQ H3C 3J7, Canada

来源：

PEPTIDE SCIENCE | 2020年 / 112卷 / 04期

基金：

加拿大自然科学与工程研究理事会;

关键词：

alpha-amino-delta-lactam; Glu-Gly; Gln-Gly; peptides; peptidomimetics; CONFORMATIONAL-ANALYSIS; ASYMMETRIC-SYNTHESIS; DESIGN; DERIVATIVES; INHIBITORS; ANALOGS; 3-AMINOLACTAMS; ISOSTERES; ACIDS;

D O I：

10.1002/pep2.24149

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：

Conformationally rigid alpha-amino-delta-lactam surrogates of Glu-Gly and Gln-Gly dipeptides have been synthesized from alpha-amino-gamma-vinyl-delta-lactam precursors. A reductive cyclization protocol from the respective (4R)- and (4S)-2-N-(Boc)amino-4-(azidomethyl)hexenoates gave delta-lactams, which were converted to the corresponding dipeptide surrogates by N-alkylation with methyl bromoacetate. The utility of these alpha-amino-gamma-vinyl-delta-lactam building blocks was demonstrated by olefin oxidation and peptide coupling to prepare constrained Glu and Gln residues.

引用

页数：7