title: Highly selective anti-Prelog synthesis of optically active aryl alcohols by recombinant Escherichia coli expressing stereospecific alcohol dehydrogenase.
abstract: Biocatalytic asymmetric synthesis has been widely used for preparation of optically active chiral alcohols as the important intermediates and precursors of active pharmaceutical ingredients. However, the available whole-cell system involving anti-Prelog specific alcohol dehydrogenase is yet limited. A recombinant Escherichia coli system expressing anti-Prelog stereospecific alcohol dehydrogenase from Candida parapsilosis was established as a whole-cell system for catalyzing asymmetric reduction of aryl ketones to anti-Prelog configured alcohols. Using 2-hydroxyacetophenone as the substrate, reaction factors including pH, cell status, and substrate concentration had obvious impacts on the outcome of whole-cell biocatalysis, and xylose was found to be an available auxiliary substrate for intracellular cofactor regeneration, by which (S)-1-phenyl-1,2-ethanediol was achieved with an optical purity of 97%e.e. and yield of 89% under the substrate concentration of 5 g/L. Additionally, the feasibility of the recombinant cells toward different aryl ketones was investigated, and most of the corresponding chiral alcohol products were obtained with an optical purity over 95%e.e. Therefore, the whole-cell system involving recombinant stereospecific alcohol dehydrogenase was constructed as an efficient biocatalyst for highly enantioselective anti-Prelog synthesis of optically active aryl alcohols and would be promising in the pharmaceutical industry.
authors.affiliation: a School of Biotechnology and Key Laboratory of Industrial Biotechnology of Ministry of Education , Jiangnan University , Wuxi , China.
authors.forename: Ming
authors.initials: M
authors.lastname: Li
authors.affiliation: a School of Biotechnology and Key Laboratory of Industrial Biotechnology of Ministry of Education , Jiangnan University , Wuxi , China.
authors.forename: Yao
authors.initials: Y
authors.lastname: Nie
authors.affiliation: a School of Biotechnology and Key Laboratory of Industrial Biotechnology of Ministry of Education , Jiangnan University , Wuxi , China.
authors.forename: Xiao Qing
authors.initials: XQ
authors.lastname: Mu
authors.affiliation: a School of Biotechnology and Key Laboratory of Industrial Biotechnology of Ministry of Education , Jiangnan University , Wuxi , China.
authors.forename: Rongzhen
authors.initials: R
authors.lastname: Zhang
authors.affiliation: a School of Biotechnology and Key Laboratory of Industrial Biotechnology of Ministry of Education , Jiangnan University , Wuxi , China.|b State Key Laboratory of Food Science and Technology , Jiangnan University , Wuxi , China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Xu
mesh_terms: D000426:Alcohol Dehydrogenase / Q000235:genetics*; D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D004926:Escherichia coli / Q000235:genetics; D011995:Recombination, Genetic; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000426:Alcohol Dehydrogenase
keywords: Active pharmaceutical ingredient; alcohol dehydrogenase; anti-Prelog reduction; aryl ketone; asymmetric synthesis; optically active alcohol