Microbial oxidation of oleic acid.
Resting cells of Saccharomyces cerevisiae (baker's yeast, type II; Sigma) were used to convert oleic acid into 10-hydroxyoctadecanoic acid with a 45% yield. Nocardia aurantia (ATCC 12674), Nocardia sp. (NRRL 5646), and Mycobacterium fortuitum (UI 53378) all converted oleic acid into 10-oxo-octadecanoic acid with 65, 55, and 80% yields, respectively. Structures of all metabolites were suggested by 1H and 13C nuclear magnetic resonance and by infrared and mass spectrometry. Structures of isomeric hydroxystearate and oxostearate derivatives and the stereochemical purity of hydroxystearates are difficult to prove unambiguously unless authentic standard compounds are available for spectral comparison. We describe the use of the chemical Baeyer-Villiger oxidation technique with 10-oxo-octadecanoic acid followed by mass spectral analysis of neutral extracts as a simple method to confirm the position of oxo-functional groups in the structures of fatty acid ketones. We further introduce a simple method based on 1H nuclear magnetic resonance analysis of diastereomeric S-(+)-O-acetylmandelate esters of hydroxystearates as a means of ascertaining stereochemical purities of hydroxy fatty acids.
el-Sharkawy
S H
SH
Division of Medicinal & Natural Products Chemistry, College of Pharmacy, University of Iowa, Iowa City 52242.
Yang
W
W
Dostal
L
L
Rosazza
J P
JP
D001419:Bacteria / Q000378:metabolism*; D001711:Biotransformation; D004951:Esterification; D005658:Fungi / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D009161:Mycobacterium / Q000378:metabolism; D009615:Nocardia / Q000378:metabolism; D019301:Oleic Acid; D009829:Oleic Acids / Q000378:metabolism* / Q000493:pharmacokinetics; D010084:Oxidation-Reduction; D012441:Saccharomyces cerevisiae / Q000378:metabolism; D013229:Stearic Acids / Q000737:chemistry / Q000378:metabolism
D009829:Oleic Acids; D013229:Stearic Acids; D019301:Oleic Acid