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Preparation of chiral secondary alcohols via enantioselective hydrolysis of corresponding esters with a microorganism.

1980/01/01 by Hiromichi Ohta, Hiromichi OHTA, Hatsuki TETSUKAWA +1 · 1 citation
Biochemistry, Genetics and Molecular Biology · Chemistry · Pharmacology, Toxicology and Pharmaceutics · #Analytical Chemistry and Chromatography #Chemical Reactions and Isotopes #Enzyme Catalysis and Immobilization

paper · pdf · doi:10.1271/bbb1961.44.863

crossref issued 1980/01/01 · crossref published 1980/01/01 · crossref published-print 1980/01/01 · openalex publication_date 1980/01/01 · 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

Esters of secondary alcohols were enantioselectively hydrolyzed with Brevibacterium ammoniagenes IAM 1645, ATCC 6872 to give the corresponding chiral alcohols and esters. While the esters of alkyl vinyl carbinols gave (S)-alcohols, dialkyl carbinol esters were hydrolyzed to (R)-alcohols of rather low optical purities. Hydrolysis of α-phenethyl acetate proceeded smoothly resulting in the formation of (R)-α-phenethyl alcohol in good optical yield. The structure of the acyl moiety of 1-tridecen-3-yl esters seriously influenced the rate and optical yield of the reaction, and the acetate was found to give the best results.

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