Synthesis of threeSalmonellaepitopes for biosensor studies of carbohydrate–antibody interactions

Abstract

Disaccharides 1-3 corresponding to the antigenic determinants of Salmonella serotypes A, B, and D1were synthesized in a form suited for use in biosensors. The disaccharide determinants each contain a unique 3,6-dideoxyhexose, namely abequose (3,6-dideoxy-D-xylo-hexose), paratose (3,6-dideoxy-D-ribohexose), and tyvelose (3,6-dideoxy-D-arabino-hexose), are α-linked to the 3-position of D-mannopyranose. The disaccharides were further derivatized with a linear aglycon that has a terminal amino group, and can be readily coupled to pertinent chains carrying a terminal thiol for the construction of self-assembled monolayers (SAMs). Efficient routes that employed a single 3,6-dideoxygenation step were developed for the synthesis of paratoside 15 and tyveloside 22.Key words: Salmonella O-antigens, lipopolysaccharide, abequose, paratose, tyvelose, 3,6-dideoxyhexose, deoxygenation, glycoside tethers, immobilization via pentenyl glycosides.