Design and synthesis of caged ceramide : UV-responsive ceramide releasing system based on UV-induced amide bond cleavage followed by O–N acyl transfer
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Sphingolipids, recognized as membrane constructs and as key signaling molecules, have been studied to examine intracellular function. Some caged sphingolipids that release parent sphingolipids after exposure to UV-irradiation have been previously developed, but caged ceramide has yet to be reported. In this study, we report the design and synthesis of a caged ceramide. Photo-irradiation experiment clarified that the caged ceramide can be successfully converted to the parent ceramide by UV-irradiation. Introduction of an alkyne-handle moiety for further modification of the caged ceramide is also reported.
Tetrahedron 67(22), 3984-3990, 2011-04-20