Conformationally Homogeneous Heterocyclic Pseudotetrapeptides as Three-Dimensional Scaffolds for Rational Drug Design: Receptor-Selective Somatostatin Analogues

被引：77

作者：

Beierle, John M. ^{[1
,2
]}

Horne, W. Seth ^{[1
,2
]}

van Maarseveen, Jan H. ^{[1
,2
]}

Waser, Beatrice ^{[3
]}

Reubi, Jean Claude ^{[3
]}

Ghadiri, M. Reza ^{[1
,2
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[3] Univ Bern, Div Cell Biol & Expt Canc Res, CH-3010 Bern, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 26期

关键词：

conformation analysis; cyclic peptides; drug design; structure-activity relationships; triazoles; AZIDE-ALKYNE CYCLOADDITION; PHARMACOLOGICAL IN-VITRO; BETA-TURN MIMICS; CYCLIC TETRAPEPTIDES; AMINO-ACIDS; PEPTIDE CONFORMATIONS; GHRELIN RECEPTOR; CLICK CHEMISTRY; BIOLOGICAL EVALUATION; CONSENSUS STRUCTURE;

D O I：

10.1002/anie.200805901

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A would-be amide: A 1,4-disubstituted 1,2,3-triazole was used as a surrogate for a trans amide bond to create a library of 16 diastereomeric pseudotetrapeptides as β-turn mimetics. Highresolution structural analysis indicated that these scaffolds adopt distinct, rigid, conformationally homogeneous β-turn-like structures (see example), some of which bind somatostatin receptor subtypes selectively, and some of which show broad-spectrum activity. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4725 / 4729

页数：5

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