| Stereocontrolled synthesis of the PPAR-gamma agonist 10-nitrolinoleic acid. | |
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MedLine Citation:
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PMID: 20593759 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The naturally occurring PPAR-gamma ligand 10-nitrooctadeca-9(E),12(Z)-dienoic acid (10-nitrolinoleic acid) (2a) was prepared as a single regio- and geometrical isomer in a practical eight-step, convergent sequence. The synthetic route featured a nitro aldol reaction between 9-oxononanoic acid methyl ester (3) and 1-nitronon-3(Z)-ene (4) in the key carbon-carbon bond forming step. The ability of 2a (and its methyl ester 9) to bind to PPAR-gamma in a ligand-binding assay is reported. |
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Authors:
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Elizabeth Dunny; Paul Evans |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 75 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2010 Aug |
Date Detail:
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Created Date: 2010-07-30 Completed Date: 2010-11-30 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 5334-6 Citation Subset: IM |
Affiliation:
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Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Ireland. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Chromatography, High Pressure Liquid Linoleic Acids / chemistry*, pharmacology Magnetic Resonance Spectroscopy Mass Spectrometry Nitro Compounds / chemistry*, pharmacology PPAR gamma / agonists* Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/10-nitro-9,12-octadecadienoic acid; 0/Linoleic Acids; 0/Nitro Compounds; 0/PPAR gamma |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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