title: A new route to L-threo-3-[4-(methylthio)phenylserine], a key intermediate for the synthesis of antibiotics: recombinant low-specificity D-threonine aldolase-catalyzed stereospecific resolution.
abstract: A new enzymatic resolution process was established for the production of L-threo-3-[4-(methylthio)phenylserine] (MTPS), an intermediate for synthesis of antibiotics, florfenicol and thiamphenicol, using the recombinant low-specificity D-threonine aldolase from Arthrobacter sp. DK-38. Chemically synthesized DL-threo-MTPS was efficiently resolved with either the purified enzyme or the intact recombinant Escherichia coli cells overproducing the enzyme. Under the optimized experimental conditions, 100 mM (22.8 g l-1) L-threo-MTPS was obtained from 200 mM (45.5 g l-1) DL-threo-MTPS, with a molar yield of 50% and a 99.6% enantiomeric excess.
authors.affiliation: Laboratory of Biocatalytic Chemistry, Toyama Prefectural University, Japan.
authors.forename: J Q
authors.initials: JQ
authors.lastname: Liu
authors.forename: M
authors.initials: M
authors.lastname: Odani
authors.forename: T
authors.initials: T
authors.lastname: Dairi
authors.forename: N
authors.initials: N
authors.lastname: Itoh
authors.forename: S
authors.initials: S
authors.lastname: Shimizu
authors.forename: H
authors.initials: H
authors.lastname: Yamada
mesh_terms: D000900:Anti-Bacterial Agents / Q000096:biosynthesis*; D003001:Cloning, Molecular; D004926:Escherichia coli; D012696:Glycine Hydroxymethyltransferase / Q000235:genetics / Q000378:metabolism*; D011401:Promoter Regions, Genetic; D012694:Serine / Q000031:analogs & derivatives* / Q000378:metabolism; D013839:Thiamphenicol / Q000031:analogs & derivatives / Q000378:metabolism
chemical_list: C120473:3-(4-(methylthio)phenylserine); D000900:Anti-Bacterial Agents; D012694:Serine; C035534:florfenicol; D012696:Glycine Hydroxymethyltransferase; D013839:Thiamphenicol