| A reinvestigation of the synthesis of arsonolipids (2,3-diacyloxypropylarsonic acids). | |
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MedLine Citation:
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PMID: 18313402 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A reinvestigation of the reactions leading to arsonolipids (2,3-diacyloxypropylarsonic acids) has been carried out in order to understand why the yields of their preparation were only moderate, although they are better than those reported for 2,3-diacyloxypropylphosphonic acid (phosphotidic acid). Thus, the reaction of glycidol and of 3-chloro-1,2-propanediol with alkaline sodium arsenite, "Na3AsO3", gives the desired product, 2,3-dihydroxypropylarsonic acid, and approximately 10% of an arsenic-containing glycerol dimer which is removed during the preparation of these arsonolipids. The step which is mainly responsible for the diminished yields is due to the reaction of the -As(SPh)2 or -AsO3H- precursor with the activated acid chlorides or carboxylic acid anhydrides to give an intermediate which cyclizes with the primary hydroxy group of the 2,3-dihydroxypropyl moiety. This cyclization does not allow the primary hydroxy group to be acylated. Such cyclization could not be avoided with RCOCl/py, (RCO)2O/DMAP, or RCOOH/DCC/DMAP acylating systems. |
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Authors:
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Gerasimos M Tsivgoulis; Panayiotis V Ioannou |
Publication Detail:
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Type: Journal Article Date: 2008-02-12 |
Journal Detail:
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Title: Chemistry and physics of lipids Volume: 152 ISSN: 0009-3084 ISO Abbreviation: Chem. Phys. Lipids Publication Date: 2008 Apr |
Date Detail:
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Created Date: 2008-04-11 Completed Date: 2008-06-26 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0067206 Medline TA: Chem Phys Lipids Country: Ireland |
Other Details:
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Languages: eng Pagination: 113-21 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Patras, Patras, Greece. tsivgoulis@chemistry.upatras.gr |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acylation Arsenicals / chemical synthesis*, chemistry* Arsenites / chemistry Binding, Competitive Carboxylic Acids / chemistry Chemistry, Physical / methods Chromatography, Thin Layer / methods Dimerization Glycerol / chemistry Lipids / chemical synthesis*, chemistry* Magnetic Resonance Spectroscopy Models, Chemical Molecular Structure Sodium Compounds / chemistry |
| Chemical | |
Reg. No./Substance:
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0/Arsenicals; 0/Arsenites; 0/Carboxylic Acids; 0/Lipids; 0/Sodium Compounds; 13768-07-5/sodium arsenite; 36465-76-6/arsonic acid; 56-81-5/Glycerol |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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