First synthesis of the beta-D-rhamnosylated trisaccharide repeating unit of the O-antigen from Xanthomonas campestris pv. campestris 8004 |
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Authors: | Bedini Emiliano Carabellese Antonella Barone Gaspare Parrilli Michelangelo |
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Institution: | Dipartimento di Chimica Organica e Biochimica, Università di Napoli "Federico II", Complesso Universitario Monte Santangelo, Via Cintia 4, 80126 Napoli, Italy. |
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Abstract: | 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. |
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