Enzymatic Conversion of α-Keto Aldehydes to Optically Active α-Hydroxy Acids Using Glyoxalase I and II

Article abstract of DOI:10.1021/jo00336a011

α-Keto aldehydes (RCOCHO, R = CH3, CH3CH2CH2, Ph, p-CH3OPh, p-ClPh) have been converted to optically active α-hydroxy acids (RCHOHCO2H) by the combined action of glutathione and the (immobilized) enzymes glyoxalase I (GX-I, EC 4.4.1.5) and glyoxalase II (GX-II, EC 3.1.2.6).The reaction seems to provide a practical if specialized method for synthesizing 1-10-g quantities of product with enantiomeric excess (ee) in the range 75-99percent.Efforts to increase the scale of the reaction are accompanied by decreases in the ee of the product and in the turnover number reached by the enzymes.