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All (S) stereoconfiguration of 7,10-dihydroxy-8(E)-octadecenoic acid from bioconversion of oleic acid by Pseudomonas aeruginosa

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Journal of the American Oil Chemists’ Society

Abstract

A previously established method was utilized to determine the stereoconfiguration of 7,10-dihydroxy-8(E)-octadecenoic acid (DHOE) from bioconversion of oleic acid by Pseudomonas aeruginosa NRRL strain B-18602 (PR3). The method involved formation of the (−)-menthoxycarbonyl (MCO) derivative of the two hydroxyls, oxidative cleavage of the double bond, and gas chromatography (GC) analysis of the two methyl-esterified diastereomeric fragments, methyl 2-MCO-decanoate and dimethyl 2-MCO-octanedioate. As described by previous workers, the 2(S)-MCO derivatives elute at earlier times by GC than the 2(R)-MCO derivatives. By comparing the GC analysis of the 2-MCO derivatives obtained from DHOE with that obtained from a partially racemized sample, DHOE was determined to be 7(S),10(S)-dihydroxy-8(E)-octadecenoic acid.

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Authors and Affiliations

  1. Bioactive Agents Research, USA

    Harold W. Gardner

  2. Oil Chemical Research, NCAUR, ARS, USDA, 61604, Peoria, Illinois

    Ching T. Hou

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  1. Harold W. Gardner
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  2. Ching T. Hou
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Correspondence to Ching T. Hou.

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Gardner, H.W., Hou, C.T. All (S) stereoconfiguration of 7,10-dihydroxy-8(E)-octadecenoic acid from bioconversion of oleic acid by Pseudomonas aeruginosa . J Am Oil Chem Soc 76, 1151–1156 (1999). https://doi.org/10.1007/s11746-999-0088-1

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  • DOI: https://doi.org/10.1007/s11746-999-0088-1

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