Synthesis of an apiose-containing disaccharide fragment of rhamnogalacturonan-II and some analogues.
Beta-rhamnosylation of methyl 2-C-hydroxymethyl-2,3-O-isopropylidene-beta-D-erythrofuranoside and methyl 2,3-O-isopropylidene-beta-D-ribofuranoside was achieved using 4-O-acetyl-2,3-O-carbonyl-alpha-L-rhamnopyranosyl bromide and Ag2O as a promoter. Deprotected disaccharides beta-L-Rhap-(1-->3')-beta-D-Apif-OMe and beta-L-Rhap-(1-->3')-beta-D-Ribf-OMe were compared to their alpha-rhamnosyl isomers which were prepared using conventional Helferich glycosylation.
Chauvin
Anne-Laure
AL
Centre for Carbohydrate Chemistry, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, UK.
Nepogodiev
Sergey A
SA
Field
Robert A
RA
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005690:Galactose / Q000737:chemistry; D006031:Glycosylation; D007536:Isomerism; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010368:Pectins / Q000737:chemistry*; D010429:Pentoses / Q000737:chemistry*; D012210:Rhamnose / Q000737:chemistry
D009844:Oligosaccharides; D010429:Pentoses; C042492:rhamnogalacturonan II; D010368:Pectins; C004983:apiose; D012210:Rhamnose; D005690:Galactose