title: Synthesis and immunodetection of 6-O-methyl-phosphoramidyl-α-D-galactose: a Campylobacter jejuni antigenic determinant.
abstract: Campylobacter jejuni is a leading cause of traveler's diarrhea. Previously, we have shown that a C. jejuni capsule polysaccharide (CPS) conjugate vaccine can fully prevent C.jejuni diarrhea in non-human primates. C.jejuni CPSs are decorated with non-stoichiometric amounts of O-methyl phosphoramidate (MeOPN) units that are key serospecific markers. In the case of C.jejuni serotype complex HS23/36, the MeOPN are at positions 2 and 6 of the CPS galactose (Gal). We describe here the synthesis of the p-methoxyphenyl glycoside of MeOPN→6-α-D-Galp, and its immunodetection by antisera raised by C.jejuni CPS conjugates with MeOPN at primary positions. The synthetic approach in this work served as the foundation for a similar MeOPN→6-Gal construct used in a conjugate vaccine, whose synthesis, immunogenicity and efficacy will be described elsewhere.
authors.affiliation: Department of Chemistry, University of Guelph, Guelph, ON, Canada N1G 2W1.
authors.forename: Yuening
authors.initials: Y
authors.lastname: Jiao
authors.affiliation: Department of Chemistry, University of Guelph, Guelph, ON, Canada N1G 2W1.
authors.forename: Zuchao
authors.initials: Z
authors.lastname: Ma
authors.affiliation: Enteric Diseases Department, Naval Medical Research Centre, Silver Spring, MD, USA.
authors.forename: Cheryl P
authors.initials: CP
authors.lastname: Ewing
authors.affiliation: Enteric Diseases Department, Naval Medical Research Centre, Silver Spring, MD, USA.
authors.forename: Patricia
authors.initials: P
authors.lastname: Guerry
authors.affiliation: Department of Chemistry, University of Guelph, Guelph, ON, Canada N1G 2W1. Electronic address: monteiro@uoguelph.ca.
authors.forename: Mario A
authors.initials: MA
authors.lastname: Monteiro
mesh_terms: D016123:Campylobacter jejuni / Q000737:chemistry / Q000276:immunology*; D002236:Carbohydrate Conformation; D005697:Galactosides / Q000138:chemical synthesis / Q000737:chemistry / Q000276:immunology*; D063088:Phosphoramides / Q000138:chemical synthesis / Q000737:chemistry / Q000276:immunology*; D011135:Polysaccharides, Bacterial / Q000138:chemical synthesis / Q000737:chemistry / Q000276:immunology*; D018074:Vaccines, Conjugate / Q000737:chemistry / Q000276:immunology*
chemical_list: C000611060:4-methoxyphenyl 6-O-methyl-phosphoramidylgalactopyranoside; D005697:Galactosides; D063088:Phosphoramides; D011135:Polysaccharides, Bacterial; D018074:Vaccines, Conjugate
keywords: Campylobacter jejuni; Capsule polysaccharide; O-methyl phosphoramidate; Synthesis; Traveler's diarrhea vaccine