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pubmed-article:15932314pubmed:abstractTextThe receptor for the lipid mediator sphingosylphosphorylcholine (SPC) has not yet been identified. We describe here the synthesis of the first photoaffinity analogue of SPC. This probe, which contains a 14C-isotopic label in the choline methyl groups and a photoreactive benzophenone in the long-chain base, may be a useful tool in the identification of the G protein coupled receptors that have been postulated to interact directly and specifically with SPC and in the definition of the ligand-binding sites. The key steps in the synthesis are selective reduction of the triple bond in enyne 6 to install the 4E double bond, Suzuki coupling to incorporate the benzophenone photophore at the end of the sphingoid chain, and reduction of the 2-azidoethyl phosphate headgroup of 13 followed by N,N,N-trimethylation to introduce the radiolabel into the choline moiety. The synthesis was completed by the release of the amino group at C2 of the sphingoid base of SPC analogue 2.lld:pubmed
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pubmed-article:15932314pubmed:authorpubmed-author:BittmanRobert...lld:pubmed
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pubmed-article:15932314pubmed:pagination4746-50lld:pubmed
pubmed-article:15932314pubmed:dateRevised2007-11-14lld:pubmed
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pubmed-article:15932314pubmed:year2005lld:pubmed
pubmed-article:15932314pubmed:articleTitleSynthesis of a photoactivatable (2S,3R)-sphingosylphosphorylcholine analogue.lld:pubmed
pubmed-article:15932314pubmed:affiliationDepartment of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, New York 11367-1597, USA.lld:pubmed
pubmed-article:15932314pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:15932314pubmed:publicationTypeResearch Support, U.S. Gov't, P.H.S.lld:pubmed
pubmed-article:15932314pubmed:publicationTypeResearch Support, N.I.H., Extramurallld:pubmed
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