Synthesis of a D-rhamnose branched tetrasaccharide, repeating unit of the O-chain from Pseudomonas syringae pv. Syringae (cerasi) 435.
The first synthesis of a d-rhamnose branched tetrasaccharide, corresponding to the repeating unit of the O-chain from Pseudomonas syringae pv. cerasi 435, as methyl glycoside is reported. The approach used is based on the synthesis of an opportune building-block, that is the methyl 3-O-allyl-4-O-benzoyl-alpha-D-rhamnopyranoside, which was then converted into both a glycosyl acceptor and two different protected glycosyl trichloroacetimidate donors. Successive couplings of these three compounds afforded the target oligosaccharide. The reported synthesis is also useful to perform the oligomerization of the repeating unit.
Bedini
Emiliano
E
Dipartimento di Chimica Organica e Biochimica, Università di Napoli 'Federico II', Complesso Universitario Monte Santangelo, Via Cintia 4, 80126 Napoli, Italy. ebedini@unina.it
Carabellese
Antonella
A
Corsaro
Maria Michela
MM
De Castro
Cristina
C
Parrilli
Michelangelo
M
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D008969:Molecular Sequence Data; D019081:O Antigens / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis*; D044224:Pseudomonas syringae / Q000737:chemistry*; D012210:Rhamnose / Q000737:chemistry*; D013237:Stereoisomerism
D019081:O Antigens; D009844:Oligosaccharides; D012210:Rhamnose