Enantioselective hydrolysis of butyl 2-ethylhexanoate by a strain of Nocardia corynebacteroides.
The results of a screen for microbial esterases that have enantioselective activity for the hydrolysis of butyl 2-ethylhexanoate are described. The preliminary screen determined that a nocardioform bacterial strain, NRRL 21057, exhibited significant activity in preferentially hydrolyzing the S enantiomer of butyl 2-ethylhexanoate. Molecular systematics methods identified NRRL 21057 as a strain of Nocardia corynebacteroides. A survey of phylogenetically related species in the genera Gordonia, Rhodococcus, and Nocardia strains demonstrated that N. corynebacteroides NRRL 21057 is the most active strain known for the specific hydrolysis of the R-isomer of butyl 2-ethylhexanoate and that it provides the S-isomer of 2-ethylhexanoate in 86% enantiomeric excess within 22 h.
Microbial Genomics and Bioprocessing Research Unit, National Center for Agriculture Utilization Research, Agricultural Research Service, U.S. Department of Agriculture, 1815 N. University Street, Peoria, IL 61604, USA. labedadp@mail.ncaur.usda.gov
David P
DP
Labeda
Michael A
MA
Jackson
Tsung Min
TM
Kuo
Lawrence K
LK
Nakamura
D002208:Caproates / Q000378:metabolism*; D004269:DNA, Bacterial / Q000737:chemistry / Q000302:isolation & purification; D004275:DNA, Ribosomal / Q000737:chemistry / Q000302:isolation & purification; D020459:Genes, rRNA; D033601:Gordonia Bacterium / Q000378:metabolism; D006868:Hydrolysis; D008969:Molecular Sequence Data; D009615:Nocardia / Q000378:metabolism*; D010802:Phylogeny; D012336:RNA, Ribosomal, 16S / Q000235:genetics; D012240:Rhodococcus / Q000378:metabolism; D017422:Sequence Analysis, DNA; D013237:Stereoisomerism; D013379:Substrate Specificity
D002208:Caproates; D004269:DNA, Bacterial; D004275:DNA, Ribosomal; D012336:RNA, Ribosomal, 16S; C040668:2-ethylhexanoic acid