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...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Asian Network for Scientific Information
2007
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| Online Access: | http://irep.iium.edu.my/24445/ http://irep.iium.edu.my/24445/1/Biotransformation_and_stereoselective_synthesis_of_pharmaceutical_molecules_from_linoleic_acid.pdf |
| _version_ | 1848779300223844352 |
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| 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 |
| building | IIUM Repository |
| collection | Online Access |
| 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. |
| first_indexed | 2025-11-14T15:15:35Z |
| format | Article |
| id | iium-24445 |
| institution | International Islamic University Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T15:15:35Z |
| publishDate | 2007 |
| publisher | Asian Network for Scientific Information |
| recordtype | eprints |
| repository_type | Digital Repository |
| 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 |
| 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 |
| title | 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_short | Biotransformation and stereoselective synthesis of pharmaceutical molecules from linoleic acid |
| title_sort | biotransformation and stereoselective synthesis of pharmaceutical molecules from linoleic acid |
| topic | QD Chemistry |
| 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 |