H-bonding directed one-step synthesis of novel macrocyclic peptides from ε-aminoquinolinecarboxylic acid

被引：47

作者：

Li, Fei ^{[1
]}

Gan, Quan ^{[2
,3
]}

Xue, Lin ^{[2
,3
]}

Wang, Zhong-ming ^{[1
]}

Jiang, Hua ^{[2
]}

机构：

[1] Beijing Univ Chem Technol, Fac Sci, Dept Organ Chem, Beijing 100029, Peoples R China

[2] Chinese Acad Sci, Inst Chem, CAS Key Lab Photochem, Beijing 100190, Peoples R China

[3] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 20期

基金：

中国国家自然科学基金;

关键词：

Macrocycles; Oligopeptides; One-step synthesis; Aggregation; SHAPE-PERSISTENT MACROCYCLE; OLIGOAMIDES; RECEPTORS; STACKING; HELICES;

D O I：

10.1016/j.tetlet.2009.02.207

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two macrocyclic peptides 1a and 1b were synthesized directly from epsilon-aminoquinoliiiecarboxylic acid 2a and 2b, respectively. The preorganization of the uncyclized intermediates mediated by hydrogen bonding assisted the cyclization. The structures of 1a and 1b were characterized by H-1 and C-13 NMR spectroscopy and MALDI-TOF MS analysis. Solid state structure of la was investigated by single crystal X-ray studies. Their aggregation behaviors in solution were studied by both variable concentration and temperature H-1 NMR experiments. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2367 / 2369

页数：3