Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000)

alpha-Galactosylceramide (alpha GalCer, KRN7000) has been identified as a modulator of immunological processes through its capacity to bind iNKT cells mediated by CD1d molecules. Some analogues in while the amide group in alpha GalCer is replaced with ester or ether groups were synthesized from D-arabinitol or L-ribose to evaluate their ability to activate iNKT cells. Ester analogues 30a, 31a, and 61 showed activity for IFN gamma and IL-4 production of iNKT cells, while ether (31b) and 4-methoxy ester (76) analogues of alpha-galactosylceramide were not active for iNKT cells. (C) 2010 Elsevier Ltd. All rights reserved.