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Start Over Author "Vijay Gnanadesikan" Journal proceedings of the national academy of sciences of the united states of america
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1. Enantioselective syntheses and biological studies of aeruginosin 298-A and its analogs: application of catalytic asymmetric phase-transfer reaction

Author

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

Subjects
Serine protease, Multidisciplinary, biology, Alkylation, Stereochemistry, Chemistry, Trypsin inhibitor, Enantioselective synthesis, Stereoisomerism, Naphthols, Asymmetric Catalysis Special Feature Part I, Catalysis, Stereocenter, Inhibitory Concentration 50, Structure-Activity Relationship, Leucine, biology.protein, Structure–activity relationship, Epoxy Compounds, Trypsin Inhibitors
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.

Published
2004

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