Surprisingly stable helical conformations in α/β-peptides by incorporation of cis-β-aminocyclopropane carboxylic acids

被引：194

作者：

De Pol, S

Zorn, C

Klein, CD

Zerbe, O

Reiser, O

机构：

[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany

[2] Univ Zurich, Inst Organ Chem, CH-8006 Zurich, Switzerland

[3] Univ Saarland, D-6600 Saarbrucken, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 04期

关键词：

alpha/beta-pepticles; beta-amino acids; foldamers; helical structures; NMR spectroscopy;

D O I：

10.1002/anie.200352267

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

With as few as seven residues, acyclic α/β-peptides, which consist of alternating units of (L)-alanine and of cis-β -amino-cyclopropanecarboxylic acids (cis-β-ACCs, see structure), form stable 313-helix turns in solution. The configuration of the cis-β-ACCs was found to be crucial for the helical structure of this new class of foldamers.

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页码：511 / 514

页数：4

相关论文

共 34 条

[1] Extracting information from the temperature gradients of polypeptide NH chemical shifts .1. The importance of conformational averaging [J].

Andersen, NH ;

Neidigh, JW ;

Harris, SM ;

Lee, GM ;

Liu, ZH ;

Tong, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (36) :8547-8561

[2] Protein prosthesis:: A semisynthetic enzyme with a β-peptide reverse turn [J].

Arnold, U ;

Hinderaker, MP ;

Nilsson, BL ;

Huck, BR ;

Gellman, SH ;

Raines, RT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (29) :8522-8523

[3] The synthesis of diastereo- and enantiomerically pure β-aminocyclopropanecarboxylic acids [J].

Beumer, R ;

Bubert, C ;

Cabrele, C ;

Vielhauer, O ;

Pietzsch, M ;

Reiser, O .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :8960-8969

[4]

BLASIO BD, 1991, BIOPOLYMERS, V31, P1181

[5]

Case D.A., 2002, AMBER 7

[6] INTRAMOLECULAR HYDROGEN-BONDING IN DERIVATIVES OF BETA-ALANINE AND GAMMA-AMINO BUTYRIC-ACID - MODEL STUDIES FOR THE FOLDING OF UNNATURAL POLYPEPTIDE BACKBONES [J].

DADO, GP ;

GELLMAN, SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) :1054-1062

[7]

DYSON HJ, 1991, ANNU REV BIOPHYS BIO, V20, P519

[8] FOLDING OF IMMUNOGENIC PEPTIDE-FRAGMENTS OF PROTEINS IN WATER SOLUTION .1. SEQUENCE REQUIREMENTS FOR THE FORMATION OF A REVERSE TURN [J].

DYSON, HJ ;

RANCE, M ;

HOUGHTEN, RA ;

LERNER, RA ;

WRIGHT, PE .

JOURNAL OF MOLECULAR BIOLOGY, 1988, 201 (01) :161-200

[9] Peptide folding induces high and selective affinity of a linear and small β-peptide to the human somatostatin receptor 4 [J].

Gademann, K ;

Kimmerlin, T ;

Hoyer, D ;

Seebach, D .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (15) :2460-2468

[10] Foldamers: A manifesto [J].

Gellman, SH .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180

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