Biocatalytic racemization of aliphatic, arylaliphatic, and aromatic alpha-hydroxycarboxylic acids.
[reaction: see text] Biocatalytic racemization of a range of aliphatic, (aryl)aliphatic, and aromatic alpha-hydroxycarboxylic acids was accomplished by using whole resting cells of a range of Lactobacillus spp. The mild (physiological) reaction conditions ensured an essentially "clean" isomerization in the absence of side reactions, such as elimination or decomposition. Whereas straight-chain aliphatic 2-hydroxycarboxylic acids were racemized with excellent rates (up to 85% relative to lactate), steric hindrance was observed for branched-chain analogues. Good rates were observed for aryl-alkyl derivatives, such as 3-phenyllactic acid (up to 59%) and 4-phenyl-2-hydroxybutanoic acid (up to 47%). In addition, also mandelate and its o-chloro analogue were accepted at a fair rate (45%). This biocatalytic racemization represents an important tool for the deracemization of a number of pharmaceutically important building blocks.
Glueck
Silvia M
SM
Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria.
Pirker
Monika
M
Nestl
Bettina M
BM
Ueberbacher
Barbara T
BT
Larissegger-Schnell
Barbara
B
Csar
Katrin
K
Hauer
Bernhard
B
Stuermer
Rainer
R
Kroutil
Wolfgang
W
Faber
Kurt
K
D000818:Animals; D001419:Bacteria / Q000201:enzymology*; D002384:Catalysis; D005227:Fatty Acids / Q000737:chemistry* / Q000378:metabolism; D006841:Hydrocarbons, Aromatic / Q000737:chemistry / Q000378:metabolism; D006880:Hydroxy Acids / Q000737:chemistry* / Q000378:metabolism; D007778:Lactobacillus / Q000201:enzymology; D013237:Stereoisomerism
D005227:Fatty Acids; D006841:Hydrocarbons, Aromatic; D006880:Hydroxy Acids