Regio- and enantio-selective reduction of .ALPHA.,.GAMMA.-diketones by fermenting bakers' yeast.
- 1 January 1986
- journal article
- Published by Oxford University Press (OUP) in Agricultural and Biological Chemistry
- Vol. 50 (10) , 2499-2502
- https://doi.org/10.1271/bbb1961.50.2499
Abstract
Reduction of various numbers of 2, 4-alkanediones by fermenting bakers' yeast has been found to be highly regio- and enantioselective, resulting in the formation of 2-hydroxy-4-alkanones. In some cases, optical purities of the products exceeded over 99% as determined by HPLC analysis of MTPA esters. The highest yield was obtained when the reaction was carried out at pH 8 with low substrate concentration. As the representative β-hydroxyketones, the absolute configuration of (+)-2-hydroxy-4-octanone (2d) and (+)-3-hydroxy-l-phenyl-l-butanone (2h) was unambiguously determined to be (S) by comparing the specific rotation of diol derivatives with those of authentic specimens.Keywords
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