Fmoc-aza-β3-Lys-OAllyl and Fmoc-aza-β3-Asp-OAllyl for on-resin head-to-tail cyclization of aza-β3-peptides

被引:1
|
作者
Abbour, Shoukri [1 ]
Baudy-Floc'h, Michele [1 ]
机构
[1] Univ Rennes 1, ICMV, ISCR, CNRS,UMR 6226, F-35042 Rennes, France
关键词
Aza-beta(3)-amino acids; Allyl protection; Lysine analog; Aspartique analog; Cyclic pseudopeptides; SOLID-PHASE SYNTHESIS; PROTECTED AZA-BETA(3)-AMINO ACIDS; ALLOC-AMINO ACIDS; ALLYLIC PROTECTION; BETA-PEPTIDE; DEPROTECTION; STRATEGY; RECOGNITION; DEPSIDES; CLEAVAGE;
D O I
10.1016/j.tetlet.2012.11.113
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rapid and efficient Fmoc/t-Bu solid-phase peptide synthesis (SPPS) of cyclic aza-beta(3)-peptide analogs by allyl strategy is described. Our synthetic approach includes the synthesis of two new aza-beta(3)-amino acids, Fmoc-aza-beta(3)-Lys-OAllyl and Fmoc-aza-beta(3)-Asp-OAllyl, then the resin attachment of the first aza-beta(3)-amino acid via its side chain, successful use of combination of three orthogonal removable protecting groups, stepwise solid-phase synthesis of linear peptide analog, and on-resin head-to-tail cyclization. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:775 / 778
页数:4
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