Asymmetric hydrolysis of esters by biochemical methods. Part V. Asymmetric hydrolysis of prochiral diesters with pig liver esterase. Preparation of optically active intermediates for the synthesis of (+)-biotin and (+)-.ALPHA.-methyl-3,4-dihydroxyphenylalanine.

1982/01/01 by Shinobu IRIUCHIJIMA, Shinobu Iriuchijima, Keiko HASEGAWA +3 · 1 citation
Biochemistry, Genetics and Molecular Biology · Pharmacology, Toxicology and Pharmaceutics · #Biochemical Acid Research Studies #Metabolism and Genetic Disorders #Pharmacogenetics and Drug Metabolism

paper · pdf · doi:10.1271/bbb1961.46.1907

crossref issued 1982/01/01 · crossref published 1982/01/01 · crossref published-print 1982/01/01 · openalex publication_date 1982/01/01 · 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

With pig liver esterase, 1, 3-dibenzyl-4, 5-cis-bis(alkyloxycarbonyl)-2-oxoimidazolidine (1) was asymmetrically hydrolyzed to (4S, 5R)-l, 3-dibenzyl-5-alkyloxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (2). This acid 2 was reduced with lithium borohydride to (4S, 5R)-l, 3-dibenzyl-5-hydroxymethyl-2-oxoimidazolidine-4-carboxylic acid lactone (3), which is known to be converted to ( + )-biotin (4). With the same esterase, diethyl 3, 4-dimethoxyphenylmethyl-(methyl)malonate (5) was asymmetrically hydrolyzed to (R)-ethyl hydrogen 3, 4-dimethoxy-phenylmethyl(methyl)malonate (6), which can be converted to (S)-α-methyl-3, 4-dihydroxyphenyl-alanine(L-a-methyldopa) (9).

Cited by

• Chiral Synthons by Ester Hydrolysis Catalyzed by Pig Liver Esterase