Synthesis ofd-Biotin Chiral Intermediates via a Biochemical Method

Autor:	Toru Yamano, Yumiko Nishiguchi, Isao Aoki, Shinji Tokuyama, Kazuo Nakahama, Kunio Takanohashi
Rok vydání:	1993
Předmět:	chemistry.chemical_classification Bicyclic molecule biology Stereochemistry Triacylglycerol lipase Alcohol General Chemistry biology.organism_classification Esterase Kinetic resolution chemistry.chemical_compound Enzyme Biotin chemistry Pseudomonas fragi
Zdroj:	Bulletin of the Chemical Society of Japan. 66:1456-1460
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.66.1456
Popis:	The enzyme-catalyzed kinetic resolution of (±)-(3aα,4α,6aα)-4-acetoxy-1,3-dibenzyl-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one [(RS)-(3a)] was examined. Lipase B from Pseudomonas fragi and rabbit liver esterase gave (−)-[3aR-(3aα,4α,6aα)]-1,3-dibenzyl-3a,4,6,6a-tetrahydro-4-hydroxy-1H-thieno[3,4-d]imidazol-2(3H)-one [(R)-(2)], while Streptomyces rochei var. volubilis gave the alcohol (S)-(2), which is a key intermediate in the synthesis of d-biotin, with high enantioselectivity.
Databáze:	OpenAIRE
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