Enantioselective Syntheses and Biological Studies of Aeruginosin 298-A and Its Analogs: Application of Catalytic Asymmetric Phase-Transfer Reaction

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 aerugin...

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Veröffentlicht in:Proceedings of the National Academy of Sciences - PNAS 2004-04, Vol.101 (15), p.5433-5438
Hauptverfasser: Fukuta, Yuhei, Ohshima, Takashi, Gnanadesikan, Vijay, Shibuguchi, Tomoyuki, Nemoto, Tetsuhiro, Kisugi, Takaya, Okino, Tatsufumi, Shibasaki, Masakatsu, Trost, Barry M.
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Sprache:eng
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Zusammenfassung: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.
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.0307154101