期刊
ACS COMBINATORIAL SCIENCE
卷 13, 期 2, 页码 107-111出版社
AMER CHEMICAL SOC
DOI: 10.1021/co100056c
关键词
alpha-helix mimetics; tris-benzamide scaffold; solid phase synthesis; protein-protein interaction
资金
- American Diabetes Association [07-07-JF-02]
- Robert A. Welch Foundation [AT-1595]
- Texas Advanced Research Program [009741-0031-2006]
Small molecules mimicking alpha-helices are of great interest since numerous protein-protein interactions use helical structures at the interface. With a goal of generating libraries of alpha-helix mimetics, an efficient solid-phase synthetic method was developed to produce tris-benzamides. The tris-benzamide scaffold was designed to place three side-chain functional groups found at the i, i+4, and i+7 positions of an alpha-helix, emulating one helical face. The synthetic strategy involves simple and iterative reactions of removal of an allyl ester, formation of an amide bond via an O -> N acyl migration, and an O-alkylation. A small library of twenty tris-benzamides containing a variety of functional groups was prepared in high purity (83-99%) to demonstrate the versatility of the synthetic approach. This methodology allowed the facile and rapid construction of alpha-helix mimetics that would facilitate the identification of small molecules for target proteins.
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