Enantioselective syntheses and biological studies of aeruginosin 298-A and its analogs: Application of catalytic asymmetric phase-transfer reaction

Yuhei Fukuta, Takashi Ohshima, Vijay Gnanadesikan, Tomoyuki Shibuguchi, Tetsuhiro Nemoto, Takaya Kisugi, Tatsufumi Okino, Masakatsu Shibasaki

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45 Citations (Scopus)

Abstract

Aeruginosin 298-A was isolated from the freshwater cyanobacterium Microcystis aeruginosa (NIES-298) and is an equipotent thrombin and trypsin inhibitor. A variety of analogs were synthesized to gain insight into the structure-activity relations. We developed a versatile synthetic process for aeruginosin 298-A as well as several attractive analogs, in which all stereocenters were controlled by catalytic asymmetric phase-transfer reaction promoted by two-center asymmetric catalysts and catalytic asymmetric epoxidation promoted by a lanthanide-BINOL complex. Furthermore, serine protease inhibitory activities of aeruginosin 298-A and its analogs were examined.

Original languageEnglish
Pages (from-to)5433-5438
Number of pages6
JournalProceedings of the National Academy of Sciences of the United States of America
Volume101
Issue number15
DOIs
Publication statusPublished - Apr 13 2004
Externally publishedYes

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All Science Journal Classification (ASJC) codes

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