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-α-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.
SYNTHESIS OF A D-RHAMNOSE BRANCHED TETRASACCHARIDE, REPEATING UNIT OF THE O-CHAIN FROM PSEUDOMONAS SYRINGAE PV. SYRINGAE (CERASI) 435 / Bedini, Emiliano; Carabellese, Antonella; Corsaro, MARIA MICHELA; DE CASTRO, Cristina; Parrilli, Michelangelo. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - STAMPA. - 339:(2004), pp. 1907-1915. [10.1016/j.carres.2004.06.010]
SYNTHESIS OF A D-RHAMNOSE BRANCHED TETRASACCHARIDE, REPEATING UNIT OF THE O-CHAIN FROM PSEUDOMONAS SYRINGAE PV. SYRINGAE (CERASI) 435
BEDINI, EMILIANO;CARABELLESE, ANTONELLA;CORSARO, MARIA MICHELA;DE CASTRO, CRISTINA;PARRILLI, MICHELANGELO
2004
Abstract
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-α-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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
