title: Biocatalytic deracemisation of aliphatic β-hydroxy esters: improving the enantioselectivity by optimisation of reaction parameters.
abstract: Optically pure aliphatic β-hydroxy esters were prepared from their racemates by deracemisation using the biocatalyst Candida parapsilosis ATCC 7330. High optical purity (up to >99 %) and good yields (up to 71 %) of the product secondary alcohols were obtained. This study highlights the importance of optimization of reaction conditions using ethyl-3-hydroxybutanoate as the model substrate to improve the enantioselectivity (enantiomeric excess from 9 to 98 %). The present study emphasises the broad substrate scope of the biocatalyst towards deracemisation. This is the first report of Candida parapsilosis ATCC 7330-mediated deracemisation of various alkyl-3-hydroxybutanoates to produce either the (R)-enantiomers (methyl, ethyl, propyl, butyl, t-butyl, allyl-3-hydroxybutanoates) or (S)-enantiomers (pentyl, iso-amyl and iso-propyl-3-hydroxybutanoates).
authors.affiliation: Laboratory of Bioorganic Chemistry, Department of Biotechnology, Indian Institute of Technology Madras, Chennai, 600 036, India.
authors.forename: Sowmyalakshmi
authors.initials: S
authors.lastname: Venkataraman
authors.forename: Anju
authors.initials: A
authors.lastname: Chadha
mesh_terms: D055162:Biocatalysis; D002087:Butyrates / Q000737:chemistry*; D002175:Candida / Q000378:metabolism*; D004952:Esters; D006863:Hydrogen-Ion Concentration; D006885:Hydroxybutyrates / Q000737:chemistry*; D050296:Microbial Viability; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D002087:Butyrates; D004952:Esters; D006885:Hydroxybutyrates