Biocatalytic racemization of sec-alcohols and alpha-hydroxyketones using lyophilized microbial cells.
Biocatalytic racemization of aliphatic and aryl-aliphatic sec-alcohols and alpha-hydroxyketones (acyloins) was accomplished using whole resting cells of bacteria, fungi, and one yeast. The mild (physiological) reaction conditions ensured the suppression of undesired side reactions, such as elimination or condensation. Cofactor and inhibitor studies suggest that the racemization proceeds through an equilibrium-controlled enzymatic oxidation-reduction sequence via the corresponding ketones or alpha-diketones, respectively, which were detected in various amounts. Ketone formation could be completely suppressed by exclusion of molecular oxygen. Figure Biocatalytic racemization whole microbial cells.
Nestl
Bettina M
BM
Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria.
Voss
Constance V
CV
Bodlenner
Anne
A
Ellmer-Schaumberger
Ursula
U
Kroutil
Wolfgang
W
Faber
Kurt
K
D000438:Alcohols / Q000737:chemistry / Q000378:metabolism*; D000818:Animals; D001419:Bacteria / Q000254:growth & development / Q000378:metabolism; D001709:Biotechnology / Q000379:methods*; D002384:Catalysis; D005233:Fatty Alcohols / Q000737:chemistry / Q000378:metabolism*; D005612:Freeze Drying; D005658:Fungi / Q000254:growth & development / Q000378:metabolism; D006801:Humans; D007659:Ketones / Q000737:chemistry / Q000378:metabolism; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D015003:Yeasts / Q000254:growth & development / Q000378:metabolism
D000438:Alcohols; D005233:Fatty Alcohols; D007659:Ketones; C011159:acyloin