Design and Synthesis of a Sphingoid Base Library

Abstract

Sphingolipids have been found to be important signaling molecules in a wide variety of biological pathways, in particular inflammation and cancer. The basic sphingolipid structure consists of three parts

a lipid chain, a linker, and a polar head group. These parts can be modified one-by-one or in combination to further elucidate the role of sphingolipids, as well as to develop and identify promising new leads in this class of compounds. Herein we report the design and synthesis of sphingolipid analogues with modifications to the linker and polar head components of the typical sphingolipid scaffold. Various pathways and synthetic routes were utilized. Through [2+3] cycloaddition and the variation of chain lengths, various library compounds were designed and synthesized.