Hydrogen-bonded self-assembled peptide nanotubes from cystine-based macrocyclic bisureas

被引:128
作者
Ranganathan, D [1 ]
Lakshmi, C
Karle, IL
机构
[1] Indian Inst Chem Technol, Discovery Lab, Hyderabad 500007, Andhra Pradesh, India
[2] USN, Res Lab, Struct Matter Lab, Washington, DC 20375 USA
关键词
D O I
10.1021/ja9903025
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The design, synthesis, and characterization of amino acid-based cyclic bisureas, a new class of macrocyclic peptides, are described. These cystine-based macrocycles are constructed by a single-step procedure involving condensation of 1,omega-alkane diisocyanate[(CH2)(n)(NCO)(2); n = 4,6, 12] with either the simple L-cystine dimethyl ester to provide simple cyclic bisureas of 16-, 18-, and 24-membered rings through 1 + 1 cyclization or with extended cystine bispeptides leading to a variety of cystine-based macrocyclic peptide bisureas. The potential of cyclic bisureas to serve as artificial receptors for 1,omega-alkane dicarboxylic acids has been demonstrated with 18- and 24-membered macrocycles which show specific binding with dianions of oxalic and succinic acid, respectively. Single-crystal X-ray studies have shown these eyelid bisureas to possess an inherent property of self-assembling into vertical stacks of tube-like structures. The hollow, open-ended tubes offer enormous scope as models for studying biological phenomena or for designing materials with novel electronic and optical properties.
引用
收藏
页码:6103 / 6107
页数:5
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