Concise synthesis of ether analogues of lysobisphosphatidic acid

被引：21

作者：

Jiang, GW

Xu, Y

Falguières, T

Gruenberg, J

Prestwich, GD

机构：

[1] Univ Utah, Dept Med Chem, Salt Lake City, UT 84108 USA

[2] Dept Biochem, CH-1211 Geneva, Switzerland

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 18期

关键词：

D O I：

10.1021/ol051194w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

收藏

页码：3837 / 3840

页数：4

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