Diversity-Oriented Syntheses of β-Substituted α-Amino γ-Lactam Peptide Mimics with Constrained Backbone and Side Chain Residues

被引：8

作者：

Geranurimi, Azade ^{[1
]}

Lubell, William D. ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 19期

基金：

加拿大自然科学与工程研究理事会;

关键词：

MITSUNOBU REACTION; DESIGN; ACID; HORMONE;

D O I：

10.1021/acs.orglett.8b02575

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-N-(Fmoc)Arnino-gamma-lactam dipeptides with a variety of beta-substituents were synthesized stereoselectively with minimal beta-elimination by routes employing, respectively, Mitsunobu chemistry and cyclic sulfamidate nucleophilic ring opening from trans- and cis-beta-hydroxy-alpha-amino-gamma-lactam pre- cursors. This diversity-oriented method provides stereochemically pure dipeptide mimics bearing Cys, Ser, Thr, Dap, Dab, His, and other amino acid residues with constrained backbone and side chain conformations.

引用

页码：6126 / 6129

页数：4

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