title: Programmed chemo-enzymatic synthesis of the oligosaccharide component of a carbohydrate-based antibacterial vaccine candidate.
abstract: The powerful chemo-enzymatic synthesis of the pentadecasaccharide hapten involved in the first synthetic carbohydrate-based vaccine candidate against endemic shigellosis is reported. The high yielding site-selective α-D-glucosylation of a lightly protected disaccharide by an engineered transglucosylase-sucrose system gave a trisaccharide, which was chemically elongated by an efficient [5+5] process.
authors.affiliation: Institut Pasteur, Unité de Chimie des Biomolécules, 28 rue du Dr Roux, 75724 Paris Cedex 15, France. laurence.mulard@pasteur.fr.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Salamone
authors.forename: Catherine
authors.initials: C
authors.lastname: Guerreiro
authors.forename: Emmanuelle
authors.initials: E
authors.lastname: Cambon
authors.forename: Isabelle
authors.initials: I
authors.lastname: André
authors.forename: Magali
authors.initials: M
authors.lastname: Remaud-Siméon
authors.forename: Laurence A
authors.initials: LA
authors.lastname: Mulard
mesh_terms: D001428:Bacterial Vaccines / Q000096:biosynthesis* / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004405:Dysentery, Bacillary / Q000517:prevention & control*; D005964:Glucosyltransferases / Q000737:chemistry / Q000378:metabolism*; D006031:Glycosylation; D006241:Haptens / Q000096:biosynthesis / Q000737:chemistry; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000096:biosynthesis* / Q000138:chemical synthesis* / Q000737:chemistry; D013395:Sucrose / Q000737:chemistry* / Q000378:metabolism
chemical_list: D001428:Bacterial Vaccines; D006241:Haptens; D009844:Oligosaccharides; D013395:Sucrose; D005964:Glucosyltransferases