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
收藏
页码：2367 / 2369
页数：3
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