title: Biotransformations of 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid and the determination of the absolute configuration of all isomers.
abstract: 2-Hydroxy-2-(ethoxyphenylphosphinyl)acetic acid, a new type of organophosphorus compound possessing two stereogenic centers, was investigated. Racemic 2-butyryloxy-2-(ethoxyphenylphosphinyl)acetic acid was synthesized and hydrolyzed using four bacterial species as biocatalysts. In all cases the reaction was more or less stereoselective and isomers bearing a phosphorus atom with an (SP)-configuration were hydrolyzed preferentially. The observed (1)H and (31)P NMR chemical shifts of Mosher esters of 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid were correlated with the configurations of both stereogenic centers of all four stereoisomers.
authors.affiliation: Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland. Electronic address: paulina.majewska@pwr.edu.pl.
authors.forename: Paulina
authors.initials: P
authors.lastname: Majewska
mesh_terms: D019342:Acetic Acid / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D001412:Bacillus subtilis / Q000378:metabolism; D001711:Biotransformation; D004926:Escherichia coli / Q000378:metabolism; D004952:Esters; D009682:Magnetic Resonance Spectroscopy; D009943:Organophosphorus Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004952:Esters; D009943:Organophosphorus Compounds; D019342:Acetic Acid
keywords: Biocatalysis; Hydroxyphosphonates; Lipolytic activity