Journal
ORGANIC LETTERS
Volume 7, Issue 18, Pages 3837-3840Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol051194w
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Funding
- NINDS NIH HHS [R01 NS029632, R01 NS029632-14] Funding Source: Medline
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We describe a versatile, efficient method for the preparation of ether analogues of (SS)-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 (SS)-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.
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