An extended beta-strand mimic for a larger artificial beta-sheet

被引:84
作者
Nowick, JS
Pairish, M
Lee, IQ
Holmes, DL
Ziller, JW
机构
[1] Department of Chemistry, University of California, Irvine, Irvine
关键词
D O I
10.1021/ja963843s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This paper reports the development of beta-strand mimic B, which duplicates the hydrogen-bonding functionality of one edge of a tetrapeptide beta-strand. When attached to a tripeptide by a suitable Linking group, beta-strand mimic B forms a hydrogen-bonded antiparallel beta-sheet structure, artificial beta-sheet 2. beta-Strand mimic B is based upon a 5-hydrazino-2-methoxybenzoic acid building block. The first half of the paper describes synthetic, IR and H-1 NMR spectroscopic, X-ray crystallographic, and molecular modeling studies of 5-hydrazino-2-methoxybenzoic acid derivatives and related molecules. These studies establish that hydrazide derivatives of 5-hydrazino-2-methoxybenzoic acid adopt a conformation similar to that of a peptide beta-strand and are suitable for use as beta-strand mimics. The second half of the paper describes synthetic and H-1 NMR spectroscopic studies of artificial beta-sheet 2 and of controls 20 and 21, which resemble the peptidomimetic and peptide strands of 2. These experiments indicate that 2 adopts a conformation and hydrogen-bonding pattern similar to that of an antiparallel beta-sheet and establish that beta-strand mimic B can induce beta-sheet formation in an attached peptide strand.
引用
收藏
页码:5413 / 5424
页数:12
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