Solid-phase synthesis of modified oligopeptides via Passerini multicomponent reaction

被引：48

作者：

Basso, A ^{[1
]}

Banfi, L ^{[1
]}

Riva, R ^{[1
]}

Piaggio, P ^{[1
]}

Guanti, G ^{[1
]}

机构：

[1] Univ Genoa, Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 11期

关键词：

protease inhibitors; multicomponent Passerini reaction; solid-supported isocyanides; photoacoustic IR spectroscopy; IBX;

D O I：

10.1016/S0040-4039(03)00238-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Passerini multicomponent reaction of N-protected-alpha-aminoaldehydes, carboxylic acids and solid-supported isocyanides has been successfully performed on Lantern(TM). The initially formed N-protected-beta-amino-alpha-acyloxyamides gave, by piperidine-promoted deprotection and concomitant acyl migration, beta-acylamino-alpha-hydroxyamides which, by OH-oxidation and cleavage off the solid support, provided beta-acylamino-alpha-oxoamides. Formation and disappearance of the isocyano group has been followed using photoacoustic IR spectroscopy, a fast, reliable and non-disruptive technique that has been successfully applied for the first time to macroscopic solid supports. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：2367 / 2370

页数：4

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