title: Evaluation of a new protocol for enzymatic dynamic kinetic resolution of 3-hydroxy-3-(aryl)propanoic acids.
abstract: The application of tandem metal-enzyme dynamic kinetic resolution (DKR) is a powerful tool for the manufacture of high-value chemical commodities. A new protocol of kinetic resolution based on irreversible enzymatic esterification of carboxylic acids with orthoesters was introduced to obtain optically active β-hydroxy esters. This procedure was combined with metal catalyzed racemization of the target substrate providing both (R) and (S) enantiomers of ethyl 3-hydroxy-3-(4-nitrophenyl)propanoate with a high yield of 89% at 40 °C. A substantial influence of the enzyme type, organic co-solvent, and metal catalyst on the conversion and enantioselectivity of the enzymatic dynamic kinetic resolution was noted.
authors.affiliation: Institute of Organic Chemistry PAS Kasprzaka 44/52, 01-224 Warsaw, Poland. ryszard.ostaszewski@icho.edu.pl.
authors.forename: Dominik
authors.initials: D
authors.lastname: Koszelewski
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Zysk
authors.forename: Anna
authors.initials: A
authors.lastname: Brodzka
authors.forename: Anna
authors.initials: A
authors.lastname: Żądło
authors.forename: Daniel
authors.initials: D
authors.lastname: Paprocki
authors.forename: Ryszard
authors.initials: R
authors.lastname: Ostaszewski
mesh_terms: D055162:Biocatalysis; D002384:Catalysis; D004800:Enzymes, Immobilized / Q000737:chemistry; D004951:Esterification; D004952:Esters / Q000737:chemistry; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D008670:Metals / Q000737:chemistry; D011422:Propionates / Q000138:chemical synthesis / Q000737:chemistry*; D011549:Pseudomonas / Q000201:enzymology*; D013237:Stereoisomerism
chemical_list: D004800:Enzymes, Immobilized; D004952:Esters; D008670:Metals; D011422:Propionates; C000608151:ethyl 3-hydroxy-3-(4-nitrophenyl)propanoate; D008049:Lipase