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Chemoenzymatic and biotransformation approaches for pharmaceutical applications

Omar, Muhammad Nor (2009) Chemoenzymatic and biotransformation approaches for pharmaceutical applications. In: 2nd National Symposium on Fermentation Technology (NSFT 2009), 14-15 December 2009, MITC Ayer Keroh Malacca. (Unpublished)

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Abstract

Methyl ricinoleate 4 and methyl 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoate 7 were subjected to epoxidation using mCPBA, or tert-butyl hydroperoxide in the presence of vanadyl acetylacetonate or titanium (IV) isopropoxide with D-(-)- or L-(+)-diisopropyl tartrate. Epoxidations using mCPBA gave equal quantities of the disatereoisomeric epoxides 5/6 and 8/9 from 4 and 7 respectively. Other methods gave preferentially epoxides 5 or 8, except for treatment of 7 with tert-butyl hydroperoxide in the presence of titanium (IV) isopropoxide and L-(+)-diisopropyl tartrate which gave preferentially epoxide 9. Hydroxy-derivative 4, 7, 5, 6, 8 and 9 were converted into the fluoro-derivatives 16 - 21 by trimethylsilylation and treament with diethylaminosulphur trifluoride. Epoxides 6 and 9 were converted into 2-oxazolines 22 and 23 respectively by reaction with acetamide.

Item Type: Conference or Workshop Item (Keynote)
Additional Information: 5626/17951
Uncontrolled Keywords: Oxygenated fatty acids, fluorinated fatty acids, expoxidation, 2-oxazolines
Subjects: Q Science > Q Science (General)
Kulliyyahs/Centres/Divisions/Institutes: Kulliyyah of Science > Department of Biotechnology
Depositing User: Prof Dr Muhammad Nor Omar
Date Deposited: 08 Mar 2012 09:56
Last Modified: 08 Mar 2012 09:56
URI: http://irep.iium.edu.my/id/eprint/17951

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