title: Enantioselective biocatalytic synthesis of (S)-monastrol.
abstract: The first enantioselective biocatalytic synthesis of (S)-monastrol has been developed via an unexpected and unusual enzymatic pathway as suitable route. Whereas attempts for a direct hydrolysis of racemic monastrol were not successful, formation of racemic O-butanoyl monastrol and subsequent enantioselective hydrolysis furnished O-butanoyl (S)-monastrol with 97% ee. Cleavage of the O-butanoyl moiety then gave the desired (S)-monastrol with 96% ee.
authors.affiliation: Department of Chemistry and Pharmacy, University of Erlangen-Nuremberg, Henkestr. 42, 91054 Erlangen, Germany.
authors.forename: Maria Alfaro
authors.initials: MA
authors.lastname: Blasco
authors.forename: Silvia
authors.initials: S
authors.lastname: Thumann
authors.forename: Jürgen
authors.initials: J
authors.lastname: Wittmann
authors.forename: Athanassios
authors.initials: A
authors.lastname: Giannis
authors.forename: Harald
authors.initials: H
authors.lastname: Gröger
mesh_terms: D055162:Biocatalysis; D002175:Candida / Q000201:enzymology; D005656:Fungal Proteins; D006868:Hydrolysis; D008049:Lipase / Q000378:metabolism; D011743:Pyrimidines / Q000096:biosynthesis*; D013237:Stereoisomerism; D013871:Thiones
chemical_list: D005656:Fungal Proteins; D011743:Pyrimidines; D013871:Thiones; C400223:monastrol; D008049:Lipase; C431349:lipase B, Candida antarctica