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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.

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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.

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