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Asymmetric hydrolysis of prochiral dimethyl 3-benzyloxycarbonylaminoglutarate with microorganisms. Preparation of (S)-3-amino-4-methoxycarbonylbutyric acid for the synthesis of carbapenem and negamycin antibiotics.

1983/01/01 by Hirokazu KOTANI, Hirokazu Kotani, Yukari KUZE +13 · 1 citation
Biochemistry, Genetics and Molecular Biology · Chemistry · Pharmacology, Toxicology and Pharmaceutics · #Analytical Chemistry and Chromatography #Enzyme Catalysis and Immobilization #Pharmacogenetics and Drug Metabolism

paper · pdf · doi:10.1271/bbb1961.47.1363

crossref issued 1983/01/01 · crossref published 1983/01/01 · crossref published-print 1983/01/01 · openalex publication_date 1983/01/01 · crossref created 2011/07/13 · crossref deposited 2022/02/18 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/30 · crossref indexed 2026/08/02

Abstract

During the synthetic study of chiral compounds with biological significance using the chemicoenzymatic approach,1>2) we found that pig liver esterase hydrolyzed the pro-2? ester of dimethyl 3-benzyloxycarbonylaminoglutarate (1) to yield the half ester 2 with an Sconfiguration. This chiral half ester 2 was used as a versatile starting material for synthesis of the carbapenem and negamycin antibiotics by the chemical transformation shown in Scheme 1.2) However, enzymes from mammalian organs such as pig liver esterase are considered to be of limited use, expensive and impractical3~5) for the large scale production of such chiral compounds. With these problems in mind, we have looked for enzymes of a

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