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Efficient synthesis of phospholipids from glycidyl phosphates
Linköping University, The Institute of Technology. Linköping University, Department of Physics, Chemistry and Biology.
Linköping University, The Institute of Technology. Linköping University, Department of Physics, Chemistry and Biology.
Linköping University, The Institute of Technology. Linköping University, Department of Physics, Chemistry and Biology, Organic Chemistry .
2002 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, Vol. 67, no 1, 194-199 p.Article in journal (Refereed) Published
Abstract [en]

New efficient routes to enantiopure phospholipids, starting from (S)-glycidol, are described. Lysophosphatidic acids and phosphatidic acids were obtained in good overall yields from (S)-glycidol, in only three and four steps, respectively. Moreover, the strategy can also be used to produce phosphatidylcholines in three steps. Using dialkylphosphoramidites, (S)-glycidol was phosphorylated to give (R)-1-O-glycidyl dialkyl phosphates. Regiospecific epoxide opening, using hexadecanol or cesium palmitate, followed by phosphate deprotection, provided lysophosphatidic acids. 2-O-Esterification prior to phosphate deprotection provided 1,2-O-diacyl and 1-O-alkyl-2-O-acyl phosphatidic acids. Phosphorylation of (S)-glycidol using phosphorus oxychloride followed by in situ treatment with choline tosylate produced (R)-glycidyl phosphocholine. Subsequent nucleophilic opening of the epoxide using cesium palmitate produced 1-O palmitoyl-sn-glycero-3-phosphocholine, which has been used in syntheses of phosphatidylcholines.

Place, publisher, year, edition, pages
2002. Vol. 67, no 1, 194-199 p.
National Category
Engineering and Technology
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URN: urn:nbn:se:liu:diva-47127DOI: 10.1021/jo010734+OAI: oai:DiVA.org:liu-47127DiVA: diva2:268023
Available from: 2009-10-11 Created: 2009-10-11 Last updated: 2011-01-13

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Lindberg, JanEkeroth, JohanKonradsson, Peter

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