Synthesis and immunodetection of 6-O-methyl-phosphoramidyl-α-D-galactose: a Campylobacter jejuni antigenic determinant. (11th December 2015)

• Record Type: Journal Article
• Authors: Jiao, Yuening; Ma, Zuchao; Ewing, Cheryl P.; Guerry, Patricia; Monteiro, Mario A.
• Is Part Of: Carbohydrate research. Volume 418(2015)
• Page Start: 9
• Page End: 12
• Publication Date: 2015-12-11
• Subjects: Campylobacter jejuni -- Capsule polysaccharide -- O-methyl phosphoramidate -- Synthesis -- Traveler's diarrhea vaccine; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2015.09.012
• Languages: English
• ISSNs: 0008-6215

Abstract

Graphical Abstract: 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-Gal p, 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.