Glycolipid antigens recognized by αβ T-cell receptors (TCRs) drive the activation of invariant natural killer T (iNKT) cells, a specialized subset of innate T lymphocytes. Glycolipids with α-linked anomeric carbohydrates have been identified as potent microbial lipid antigens for iNKT cells, and their unusual α-anomeric linkage has been thought to define a "foreign" lipid antigen motif. However...

When using benzyl ethers as permanent protecting groups in oligosaccharide synthesis selective oxidative debenzylation with NaBrO(3) + Na(2)S(2)O(4) under biphasic conditions is efficient and compatible with anomeric azides and many other functions.

Acid-base catalyzed glycosyl donor and then glycosyl acceptor activation with phenylboron difluoride or diphenylboron fluoride permits hydrogen bond mediated intramolecular S(N)2-type glycosidation in generally high anomeric selectivity.

α-Nitrophenyl derivatives of glycosides are convenient substrates used to detect and characterize α-N-acetylgalactosaminidase. A new procedure combining chemical biocatalytic steps was developed prepare 4-nitrophenyl-2-acetamido-2-deoxy-α-D-galactopyranoside (4NP-α-GalNAc). The α-anomer prepared through synthesis an anomeric mixture followed by selective removal the β-anomer using specific enzy...

Electrospray ionization and collision induced dissociation on a triple quadrupole mass spectrometer were used to determine the effect of spatial crowding of incremented alkyl groups of two anomeric pairs of peralkylated (methyl to pentyl) disaccharides (maltose/cellobiose and isomaltose/gentiobiose). Protonated molecules were generated which underwent extensive fragmentation under low energy co...

This manuscript describes the preparation and the spectroscopic characterisation of semi-synthetic sulfated maltotriose C-C linked dimers (SMTCs) where the natural C-O-C anomeric bond was substituted by one direct central C-C bond. This C-C bond induces conformation and flexibility changes with respect to the usual anomeric bond. SMTCs neutral precursors came from maltotriosyl bromide electrore...

A new mixture of alkyl glycosides derived from palm oil (PO) or palm kernel oil (PKO) was synthesised. This mixture contains glycosylated disaccharide of either maltose or lactose with aliphatic chain that varies according to the PO or PKO fatty acids composition. The synthesis method produced no polymerised sugar unlike the production of the commercial glycosides (APG). The mixture only contai...