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Chemo‐enzymatic D ‐enantiomerization of DL ‐lactate
Author(s) -
Oikawa Tadao,
Mukoyama Shuji,
Soda Kenji
Publication year - 2001
Publication title -
biotechnology and bioengineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.136
H-Index - 189
eISSN - 1097-0290
pISSN - 0006-3592
DOI - 10.1002/1097-0290(20010405)73:1<80::aid-bit1039>3.0.co;2-t
Subject(s) - sodium lactate , ethyl lactate , chemistry , enantiomer , sodium pyruvate , sodium borohydride , yield (engineering) , lactic acid , enantiomeric excess , stereochemistry , chromatography , organic chemistry , enantioselective synthesis , biochemistry , catalysis , sodium , biology , bacteria , materials science , metallurgy , genetics
We investigated the total conversion of racemic lactate, L ‐lactate, and pyruvate into D ‐lactate, which is very useful as a starting material for the synthesis of chiral compounds and much more valuable than the L ‐enantiomer by means of coupling of L ‐specific oxidation of the racemate with L ‐lactate oxidase and non‐enantio‐ specific reduction of pyruvate to DL ‐lactate with sodium borohydride. In this one‐pot system, L ‐lactate was enantiospecifically oxidized to an achiral product, pyruvate, which was chemically reduced to DL ‐lactate leading to a turnover. Consequently, either DL ‐lactate, L ‐lactate, or pyruvate was fully converted to the D ‐enantiomer. We optimized the reaction conditions: DL ‐lactate was converted to D ‐lactate in 99% of the theoretical yield and with more than 99% enantiomeric excess. DL ‐α‐Hydroxybutyrate and α‐ketobutyrate were converted also to D ‐α‐hydroxybutyrate in the same way, though slowly. © 2001 John Wiley & Sons, Inc. Biotechnol Bioeng 73: 80–82, 2001.