Synthesis of glycolipids for NKT cell stimulation

Date of Completion

January 2011


Chemistry, Biochemistry|Chemistry, Organic|Health Sciences, Immunology




Natural Killer T (NKT) cells are a subset of mature T lymphocytes which have been shown to play a major role in controlling immune responses. Recently, it has become evident that the antigen receptor expressed by NKT cells recognize glycolipids presented by CD1d, a major-histocompatibility complex class I-like molecule expressed on dendritic cells, monocytes, and a subgroup of B cells. Via recognition of glycolipids by NKT cells, various cytokines are released which influence other cells of the immune system. A synthetic α-galactosylceramide, KRN 7000, was shown to possess anti-tumor and immunostimulatory activities. To further understand the significant biological activities of glycolipids, in this thesis we describe the synthesis of an OCH analogue, α-S-GalCer, and a series of carbohydrate modified analogues of KRN 7000. ^