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pubmed-article:16119911pubmed:abstractTextWe describe a versatile, efficient method for the preparation of ether analogues of (S,S)-lysobisphosphatidic acid (LBPA) and its enantiomer from (S)-solketal. Phosphorylation of a protected sn-2-O-octadecenyl glyceryl ether with 2-cyanoethyl bis-N,N-diisopropylamino phosphine and subsequent deprotection generated the bisether LBPA analogues. By simply changing the sequence of deprotection steps, we obtained the (R,R)- and (S,S)-enantiomers of 2,2'-bisether LBPA. An ELISA assay with anti-LBPA monoclonal antibodies showed that the bisether LBPAs were recognized with the same affinity as the natural 2,2'-bisoleolyl LBPA. [reaction: see text]lld:pubmed
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pubmed-article:16119911pubmed:authorpubmed-author:PrestwichGlen...lld:pubmed
pubmed-article:16119911pubmed:authorpubmed-author:XuYongYlld:pubmed
pubmed-article:16119911pubmed:authorpubmed-author:GruenbergJean...lld:pubmed
pubmed-article:16119911pubmed:authorpubmed-author:FalguièresTho...lld:pubmed
pubmed-article:16119911pubmed:authorpubmed-author:JiangGuoweiGlld:pubmed
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pubmed-article:16119911pubmed:pagination3837-40lld:pubmed
pubmed-article:16119911pubmed:dateRevised2010-9-21lld:pubmed
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pubmed-article:16119911pubmed:year2005lld:pubmed
pubmed-article:16119911pubmed:articleTitleConcise synthesis of ether analogues of lysobisphosphatidic acid.lld:pubmed
pubmed-article:16119911pubmed:affiliationDepartment of Medicinal Chemistry, The University of Utah, 419 Wakara Way, Suite 205, Salt Lake City, UT 84108-1257, USA.lld:pubmed
pubmed-article:16119911pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:16119911pubmed:publicationTypeResearch Support, U.S. Gov't, P.H.S.lld:pubmed
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pubmed-article:16119911pubmed:publicationTypeResearch Support, N.I.H., Extramurallld:pubmed