Microbial Enantioselective Ester Hydrolysis for the Preparation of Optically Active 4,1-Benzoxazepine-3-acetic Acid Derivatives as Squalene Synthase Inhibitors

Microbial enantioselective ester hydrolysis for the preparation of optically active (3R, 5S)-(−)-5-phenyl-4,1-benzoxazepine-3-acetic acid derivatives as potent squalene synthase inhibitors was investigated. Pseudomonas diminuta and Pseudomonas taetrolens hydrolyzed the racemic ethyl ester of the 5-(...

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Bibliographic Details
Published in:	Chemical & pharmaceutical bulletin Vol. 50; no. 1; pp. 59 - 65
Main Authors:	Tarui, Naoki, Nakahama, Kazuo, Nagano, Yoichi, Izawa, Motowo, Matsumoto, Kiyoharu, Kori, Masakuni, Nagata, Toshiaki, Miki, Takashi, Yukimasa, Hidefumi
Format:	Journal Article
Language:	English
Published:	Tokyo The Pharmaceutical Society of Japan 2002 Maruzen Japan Science and Technology Agency
Subjects:	4,1-benzoxazepine-3-acetic acid Animals asymmetric hydrolysis Azepines - chemistry Azepines - metabolism Azepines - pharmacology Biological and medical sciences Biotechnology Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Esters Farnesyl-Diphosphate Farnesyltransferase - antagonists & inhibitors Fundamental and applied biological sciences. Psychology Health. Pharmaceutical industry Humans Hydrolysis hypocholestemic agent Industrial applications and implications. Economical aspects Liver - drug effects Liver - enzymology Male Other active biomolecules Production of active biomolecules Pseudomonas - metabolism Pseudomonas sp. S-13 Pseudomonas taetrolens Rats Rats, Sprague-Dawley squalene synthase Stereoisomerism Structure-Activity Relationship Tumor Cells, Cultured Pseudomonadales Enantioselectivity Enzyme Transferases Lactam Enzyme inhibitor Screening test Farnesyl-diphosphate farnesyltransferase In vitro Cholesterol Pseudomonas taetrolens Asymmetric synthesis Carboxylic acid Chlorine Organic compounds Bicyclic compound Bacteria Pseudomonadaceae Aromatic compound Chemical synthesis Enantiomer(-) Antilipemic agent Oxygen nitrogen heterocycle Enzymatic reaction
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