First synthesis of the beta-D-rhamnosylated trisaccharide repeating unit of the O-antigen from Xanthomonas campestris pv. campestris 8004.
The trisaccharide repeating unit of the O-antigen of the lipopolysaccharide from Xanthomonas campestris pv. campestris 8004, a pathogen of cruciferous crops, presents some structural features that renders it a challenging synthetic target: the presence of a beta-D-rhamnosidic linkage, the steric crowd on a 1,2-cis-diglycosylated D-rhamnose, and finally the noncommercial availability of its monosaccharide constituents. The synthesis of this trisaccharide as methyl glycoside has been accomplished by exploiting a strategy whose key steps were the sequential beta-D-rhamnosylation with a 2-O-benzylsulfonyl-N-phenyltrifluoroacetimidate donor, debenzylsulfonylation, and coupling with a D-Fucp3NAc thioglycoside donor.
Bedini
Emiliano
E
Dipartimento di Chimica Organica e Biochimica, Università di Napoli "Federico II", Complesso Universitario Monte Santangelo, Via Cintia 4, 80126 Napoli, Italy.
Carabellese
Antonella
A
Barone
Gaspare
G
Parrilli
Michelangelo
M
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D008969:Molecular Sequence Data; D019081:O Antigens / Q000737:chemistry*; D010935:Plant Diseases / Q000382:microbiology; D012210:Rhamnose; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D016959:Xanthomonas campestris / Q000737:chemistry* / Q000472:pathogenicity
D004187:Disaccharides; D019081:O Antigens; D014312:Trisaccharides; D012210:Rhamnose