Synthesis of homoceramides, novel ceramide analogues, and their lack of effect on the growth of hippocampal neurons

S De Jonghe, I Lamote, K Venkataraman…

Index: De Jonghe, Steven; Lamote, Inge; Venkataraman, Krishnan; Boldin, Swetlana A.; Hillaert, Ulrik; Rozenski, Jef; Hendrix, Chris; Busson, Roger; De Keukeleire, Denis; Van Calenbergh, Serge; Futerman, Anthony H.; Herdewijn, Piet Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 988 - 996

Full Text: HTML

Citation Number: 16

Abstract

The synthesis of a new series of d-erythro-homoceramide analogues is described. Several synthetic approaches were investigated. Homoceramides can be successfully synthesized from l-homoserine as chiral building block and a protected Weinreb-amide as a key intermediate. The synthesis of short-chain analogues with a heptyl side chain, as well as with a phenyl residue in the sphingoid part (instead of the naturally occurring tridecyl side ...