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

AUTOR(ES)

Fukuta, Yuhei

FONTE

National Academy of Sciences

RESUMO

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.

Documentos Relacionados

• ACETYLCHOLINE AND ITS THIOLESTER AND SELENOLESTER ANALOGS: CONFORMATION, ELECTRON DISTRIBUTION, AND BIOLOGICAL ACTIVITY*
• beta-Endorphin omission analogs: dissociation of immunoreactivity from other biological activities.
• Solid-phase synthesis of chiral 3,4-diazaphospholanes and their application to catalytic asymmetric allylic alkylation
• Inhibition of ribonucleotide reductase by 2'-substituted deoxycytidine analogs: possible application in AIDS treatment.
• Studies on angiotensin II and analogs: impact of substitution in position 8 on conformation and activity.