Nonpeptidic foldamers from amino acids: Synthesis and characterization of 1,3-substituted triazole oligomers

被引：191

作者：

Angelo, NG ^{[1
]}

Arora, PS ^{[1
]}

机构：

[1] NYU, Dept Chem, New York, NY 10003 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 49期

关键词：

D O I：

10.1021/ja056406z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nonpeptidic foldamers capable of displaying protein-like functionality were prepared by swapping amide bonds with 1,2,3-triazole rings. The overall conformation of these triazole oligomers is largely dictated by dipole-dipole interactions between adjacent rings. Solution NMR studies suggest that a zigzag conformation, which closely mimics the β-strand structure, predominates in two different tetramers. Copyright © 2005 American Chemical Society.

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页码：17134 / 17135

页数：2

相关论文

共 21 条

[1] Metal catalyzed diazo transfer for the synthesis of azides from amines [J].

Alper, PB ;

Hung, SC ;

Wong, CH .

TETRAHEDRON LETTERS, 1996, 37 (34) :6029-6032

[2] Bioinspired polymeric materials: in-between proteins and plastics [J].

Barron, AE ;

Zuckermann, RN .

CURRENT OPINION IN CHEMICAL BIOLOGY, 1999, 3 (06) :681-687

[3] Freeze-frame inhibitor captures acetylcholinesterase in a unique conformation [J].

Bourne, Y ;

Kolb, HC ;

Radic, Z ;

Sharpless, KB ;

Taylor, P ;

Marchot, P .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (06) :1449-1454

[4] 1,2,3-triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors [J].

Brik, A ;

Alexandratos, J ;

Lin, YC ;

Elder, JH ;

Olson, AJ ;

Wlodawer, A ;

Goodsell, DS ;

Wong, CH .

CHEMBIOCHEM, 2005, 6 (07) :1167-+

[5] β-peptides:: From structure to function [J].

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232

[6] Orfanolithium-mediated diversification of peptide thiazoles [J].

Deng, SJ ;

Taunton, J .

ORGANIC LETTERS, 2005, 7 (02) :299-301

[7] Foldamers: A manifesto [J].

Gellman, SH .

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

[8] A field guide to foldamers [J].

Hill, DJ ;

Mio, MJ ;

Prince, RB ;

Hughes, TS ;

Moore, JS .

CHEMICAL REVIEWS, 2001, 101 (12) :3893-4011

[9] MEDICINAL CHEMISTRY IN THE GOLDEN-AGE OF BIOLOGY - LESSONS FROM STEROID AND PEPTIDE RESEARCH [J].

HIRSCHMANN, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (10) :1278-1301

[10] A cis amide bond surrogate incorporating 1,2,4-triazole [J].

Hitotsuyanagi, Y ;

Motegi, S ;

Fukaya, H ;

Takeya, K .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10) :3266-3271