Preparation of Nitrogen Analogues of Ceramide and Studies of Their Aggregation in Sphingomyelin Bilayers.

Ceramides can regulate biological processes probably through the formation of laterally segregated and highly packed ceramide-rich domains in lipid bilayers. In the course of preparation of its analogues, we found that a hydrogen-bond-competent functional group in the C1 position is necessary to form ceramide-rich domains in lipid bilayers [Matsufuji; 2018]. Hence, in the present study, we newly synthesized three ceramide analogues: CerN, CerNH, and CerNHAc, in which the 1-OH group of ceramide is substituted with a nitrogen functionality.