Affiliation:
1. Division of Medicinal & Natural Products Chemistry, College of Pharmacy and Center for Biocatalysis and Bioprocessing, University of Iowa, Iowa City, Iowa 52242
Abstract
We recently described a simple method for ascertaining the stereochemical purities of hydroxy fatty acids (S. H. El-Sharkawy, W. Yang, L. Dostal, and J. P. N. Rosazza, Appl. Environ. Microbiol. 58:2116-2122, 1992) based on the
1
H-nuclear magnetic resonance spectral analysis of diastereomeric
S
-(+)-
O
-acetylmandelate esters of hydroxystearates. This report describes the stereochemistries of microbial hydrations of oleic acid to 10-hydroxystearic acid by
Nocardia aurantia
(also known as
Rhodococcus rhodochrous
) ATCC 12674,
Nocardia restrictus
ATCC 14887,
Mycobacterium fortuitum
UI-53387,
Pseudomonas
species strain NRRL-2994,
Pseudomonas
species strain NRRL B-3266, and baker's yeast. 10(
R
)-hydroxystearic acid isolated from
Pseudomonas
species strain NRRL-2994 was the standard for use in the
1
H-nuclear magnetic resonance spectral technique to permit simple assignments of the absolute configurations of 10-hydroxystearic acid produced by different microorganisms. While the
R. rhodochrous
ATCC 12674-mediated hydration of oleic acid gave mixtures of enantiomers 10(
R
)-hydroxystearic acid and 10(
S
)-hydroxystearic acid,
Pseudomonas
species strain NRRL-B-3266 produced optically pure 10(
R
)-hydroxystearic acid. The remaining microorganisms stereoselectively hydrated oleic acid to 10(
R
)-hydroxystearic acid containing between 2 and 18% of the contaminating 10(
S
)-hydroxystearic acid.
Publisher
American Society for Microbiology
Subject
Ecology,Applied Microbiology and Biotechnology,Food Science,Biotechnology
Reference19 articles.
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4. Microbial hydration of cis-9-alkenoic acids;Davis E. N.;Lipids,1969
5. Microbial oxidation of oleic acid;El-Sharkawy S. H.;Appl. Environ. Microbiol.,1992
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