Journal of Pure and Applied MicrobiologyVol. 8 No. 2

Kinetic Resolution of Racemic 1-phenyl-1,2-ethanediol Via Gluconobacter oxydans-catalyzed Asymmetric Bio-oxidation

Li Dai-Huan, Wei Dong-Zhi and Lin Jin-Ping*

State Key Laboratory of Bioreactor Engineering, NewWorld Institute of Biotechnology, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, China.

Received on 20 October 2013 and accepted on 02 January 2014

 

ABSTRACT

Optically pure (S)-1-phenyl-1,2-ethanodiol(PED) is a versatile chiral building block for the synthesis of pharmaceuticals, pheromones and liquid crystals. An alternative and convenient biocatalytic process was developed for the preparation of (S)-PED by Gluconobacter oxydans-catalyzed optical resolution of the corresponding racemate. Whole cells of G. oxydans DSM2003 were found to catalyze the regio- and stereo-selective concurrent oxidation of racemic PED to give (S)-PED with the optical purity of 99% and yield of 38% in 10h, meanwhile (R)-mandelic acid with moderate ee value produced. This oxidation is carried out by two sets of enzymes, the one made of membrane-bound alcohol dehydrogenase is responsible for the PED oxidation to hydroxyl aldehyde intermediate and the other composed of membrane-bound aldehyde dehydrogenase and other enzymes is responsible for the mandelic acid production.

Keywords : Gluconobacter oxydans, 1-phenyl-1,2-ethanodiol, Mandelic acid, Oxidative Resolution, Biocatalysis.