Biotransformation and stereoselective synthesis of pharmaceutical molecules from linoleic acid

Biotransformation and stereoselective synthesis of pharmaceutical molecules from linoleic acid

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 subjec...

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Main Authors: Omar, Muhammad Nor, Muhd Nor, Nor Nazuha, Moynihan, Humphrey, Hamilton, Richard J.
Format: Article
Language:English
Published: Asian Network for Scientific Information 2007
Subjects:
QD Chemistry
Online Access:http://irep.iium.edu.my/24445/
http://irep.iium.edu.my/24445/
http://irep.iium.edu.my/24445/1/Biotransformation_and_stereoselective_synthesis_of_pharmaceutical_molecules_from_linoleic_acid.pdf
id iium-24445
recordtype eprints
spelling iium-244452012-08-13T04:15:01Z http://irep.iium.edu.my/24445/ Biotransformation and stereoselective synthesis of pharmaceutical molecules from linoleic acid Omar, Muhammad Nor Muhd Nor, Nor Nazuha Moynihan, Humphrey Hamilton, Richard J. QD Chemistry 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. Asian Network for Scientific Information 2007 Article PeerReviewed application/pdf en http://irep.iium.edu.my/24445/1/Biotransformation_and_stereoselective_synthesis_of_pharmaceutical_molecules_from_linoleic_acid.pdf 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) http://docsdrive.com/pdfs/ansinet/biotech/2007/283-287.pdf
repository_type Digital Repository
institution_category Local University
institution International Islamic University Malaysia
building IIUM Repository
collection Online Access
language English
topic QD Chemistry
spellingShingle QD Chemistry
Omar, Muhammad Nor
Muhd Nor, Nor Nazuha
Moynihan, Humphrey
Hamilton, Richard J.
Biotransformation and stereoselective synthesis of pharmaceutical molecules from linoleic acid
description 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.
format Article
author Omar, Muhammad Nor
Muhd Nor, Nor Nazuha
Moynihan, Humphrey
Hamilton, Richard J.
author_facet Omar, Muhammad Nor
Muhd Nor, Nor Nazuha
Moynihan, Humphrey
Hamilton, Richard J.
author_sort Omar, Muhammad Nor
title Biotransformation and stereoselective synthesis of pharmaceutical molecules from linoleic acid
title_short Biotransformation and stereoselective synthesis of pharmaceutical molecules from linoleic acid
title_full Biotransformation and stereoselective synthesis of pharmaceutical molecules from linoleic acid
title_fullStr Biotransformation and stereoselective synthesis of pharmaceutical molecules from linoleic acid
title_full_unstemmed Biotransformation and stereoselective synthesis of pharmaceutical molecules from linoleic acid
title_sort biotransformation and stereoselective synthesis of pharmaceutical molecules from linoleic acid
publisher Asian Network for Scientific Information
publishDate 2007
url http://irep.iium.edu.my/24445/
http://irep.iium.edu.my/24445/
http://irep.iium.edu.my/24445/1/Biotransformation_and_stereoselective_synthesis_of_pharmaceutical_molecules_from_linoleic_acid.pdf
first_indexed 2023-09-18T20:36:39Z
last_indexed 2023-09-18T20:36:39Z
_version_ 1777409090276818944

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