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Microbial oxidation of oleic acid
S H el-Sharkawy1, W Yang, L Dostal
1Division of Medicinal & Natural Products Chemistry, College of Pharmacy, University of Iowa, Iowa City 52242.
Applied and Environmental Microbiology
|July 1, 1992
Summary
Baker's yeast and Nocardia species convert oleic acid into hydroxy and oxo fatty acids, respectively. New methods confirm the structure and stereochemistry of these valuable compounds.
Area of Science:
- Biotechnology
- Organic Chemistry
- Microbiology
Background:
- Microbial biotransformation offers a sustainable route for producing valuable fatty acid derivatives.
- Accurate structural and stereochemical elucidation of these derivatives is crucial for their applications.
Purpose of the Study:
- To investigate the microbial conversion of oleic acid into hydroxy- and oxo-octadecanoic acids.
- To develop and validate analytical methods for confirming the structure and stereochemical purity of these fatty acid metabolites.
Main Methods:
- Microbial biotransformation using Saccharomyces cerevisiae, Nocardia aurantia, and Mycobacterium fortuitum.
- Structural characterization using Nuclear Magnetic Resonance (NMR), Infrared (IR), and Mass Spectrometry (MS).
- Chemical Baeyer-Villiger oxidation and analysis of diastereomeric esters for structural confirmation.
Main Results:
- Saccharomyces cerevisiae yielded 45% 10-hydroxyoctadecanoic acid from oleic acid.
- Nocardia species produced 10-oxo-octadecanoic acid with yields ranging from 55% to 80%.
- Novel chemical and NMR-based methods were successfully employed for structural and stereochemical analysis.
Conclusions:
- Microbial biotransformation is effective for producing hydroxy- and oxo-fatty acids.
- The developed methods provide reliable means for unambiguous structural and stereochemical determination.
- This study contributes to the efficient synthesis and characterization of specialty fatty acids.