Synthesis of sphingomyelin analogues toward evaluating its physical properties in raft domain

Abstract

Raft domain is the lipid microdomain, which consist of sphingomyelin and cholesterol as major components. Generally, this particular domain is considered to play a key role in processes such as membrane trafficking and signal transduction. However, the effective role of sphingomyelin to construct the raft domain has not been understood. We designed three types of sphingomyelin analogues, in which the oxygen atom connecting the phosphocholine head group to the sphingosine backbone was replaced with CH2, NH, and S groups, and examined their physical properties. In this symposium, we report the syntheses of three sphingomyelin analogues by our own olefin cross methathesis protocol, which can provide various kinds of sphingomyelin delivatives, as a key step. We also report their physical properties, in particular their packing phenomena of raft domain comparing with the natural one.