Syntheses of sphingomyelin methylene, aza, and sulfur analogues by the versatile olefin cross-metathesis method

Abstract

The syntheses of optically homogeneous sphingomyelin analogues, which possess CH 2, NH, and S instead of the phosphate oxygen connecting the phosphocholine head group to the sphingosine backbone, were successfully achieved by employing the olefin cross-metathesis protocol between 1-pentadecene and the amino alcohol parts possessing the suitable building block or functional group for construction of the phosphocholine moiety. In addition, fluorescence-labeled sphingomyelin methylene analogue was also synthesized.