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Biotransformation and stereoselective synthesis of pharmaceutical molecules from linoleic acid

Omar, Muhammad Nor and Muhd Nor, Nor Nazuha and Moynihan, Humphrey and Hamilton, Richard J. (2007) Biotransformation and stereoselective synthesis of pharmaceutical molecules from linoleic acid. Biotechnology, 6 (2). pp. 283-287. ISSN 1682-2978 (O), 1682-296X (P)

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The biotransformation of linoleic acid 1 using immobilised soybean lipoxygenase in a dimethyl sulfoxide (DMSO) containing medium followed by sodium borohydride reduction afforded 13(S)-hydroxy-octadeca-9(Z),11(E)-dienoic acid 13(S)-HODE 2 in 69% yield. After methylation, methyl 13(S)-HODE was subjected to epoxidation using tert-butyl hydroperoxide (TBHP) in the presence of vanadyl acetylacetonate or titanium (IV) isopropoxide with D-(-)- or L-(+)-diisopropyl tartrate. Epoxidation catalysed by titanium (IV) isopropoxide/D-(-)-isopropyl tartarate gave predominantly epoxide 3 (in 75% yield) while treatment of 2 with TBHP in the presence of titanium (IV) isopropoxide and L-(+)-diisopropyl tartrate gave preferentially epoxide 4 in 73% yield. Meanwhile, epoxidation of 2 with TBHP in the presence of vanadyl acetylacetonate gave predominantly epoxide 3 in 72% yield. The fluoro-derivatives 8, 9 and 10 were obtained in high yield when hydroxy-derivative 2, 3 and 4 were converted into their trimethylsilyl derivatives 5, 6 and 7 before treating with diethylaminosulphur trifluoride. Treatment of epoxide 4 with acetamide in dimethyl formamide (DMF) afforded a heterocyclic 2-oxazoline 11 in 73% yield.

Item Type: Article (Journal)
Additional Information: 5625/24445
Uncontrolled Keywords: Biotransformation ; linoleic acid ; lipoxygenase ; pharmaceutical molecules
Subjects: Q Science > QD Chemistry
Kulliyyahs/Centres/Divisions/Institutes (Can select more than one option. Press CONTROL button): Kulliyyah of Science > Department of Biotechnology
Depositing User: Prof Dr Muhammad Nor Omar
Date Deposited: 13 Aug 2012 10:49
Last Modified: 13 Aug 2012 12:15
URI: http://irep.iium.edu.my/id/eprint/24445

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