Solid-phase synthesis of a type II′ β-turn peptido-mimetic library

被引：11
作者：
Grimes, JH
Angell, YM
Kohn, WD
机构：
[1] Eli Lilly & Co, Sphinx Labs, Res Triangle Pk, NC 27709 USA
[2] Affymax Inc, Palo Alto, CA 94304 USA
[3] Lilly Corp Ctr, Lilly Res Labs, Indianapolis, IN 46285 USA
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 19期
关键词：
beta-turn mimetics; Pictet-Spengler reaction; solid-phase synthesis; IBTM;
D O I：
10.1016/S0040-4039(03)00701-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The solid-phase synthesis of a dipeptide derived 2-amino-3-oxohexahydroindolizino[8,7-b]indole-5-carboxylate system (IBTM) is described. The IBTM moiety is formed via a solid-phase mediated Pictet-Spengler reaction of N-terminal tryptophan and the 4-{N-[1-(4,4-dimethyl-2,6-dioxocyclobexylidene)-3-methylbutyl]amino}benzyl (Dmab) ester of Fmoc protected aspartic acid beta-aldehyde followed by gamma-lactamization. This synthesis allows the regio- and stereoselective incorporation of a dipeptide surrogate of type II' beta-turns. The procedure is easily adaptable to combinatorial synthesis and a 576-member library was synthesized. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3835 / 3838
页数：4
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