Abstract: Glycosylceramide analogues are disclosed in which the ceramide moiety and optionally the carbohydrate moiety are modified or replaced. These analogues are useful as immunomodulators, antitumor agents, and as other pharmaceutical agents.

Abstract: A glycolipopeptide comprising at least one disease-associated epitope, and characterized by at least one lipidated interior amino acid or by the presence of a MUC1 epitope, may be used in a vaccine, preferably in conjunction with a liposome.

Abstract: The core structure of pentaerythritol has been used as a replacement for one or both sugars in lipid A, leading to the generation of a series of lipid A analogs. These lipid A analogs may further differ from lipid A with respect to, e.g., the number, nature and location of negatively charged groups, and the number, nature and location of the lipid chains. The lipid A analogs may be lipid A agonists useful as immunostimulatory agents, or lipid A antagonists useful in the treatment of septic shock. In a like manner, a residue of pentaerythritylamine may be used as a replacement for an amino sugar residue in a carbohydrate ligand having a biological activity of interest, generating a series of ligand analogs. These are useful, e.g., as haptens, inhibitors of bacterial-host cell adhesion, etc.

Abstract: A stereodirected process for synthesizing .alpha.-N-acetylgalactosaminides from N-acetylgalactosamine which, in a preferred embodiment, comprises:reacting N-acetylgalactosamine with a dialkyl acetal of an aldehyde or ketone to form a 4,6-O-alkylidene derivative;reacting said 4,6-O-alkylidene derivative with a protecting group compound to attach a protecting group selectively to 3-OH of said derivative to form a 3-O-protected derivative;reacting said 3-O-protected derivative with an anomeric group to form a glycosyl donor;reacting said glycosyl donor with an alcohol to form an N-acetylgalactosaminide.