Synthesis of an apiose-containing disaccharide fragment of rhamnogalacturonan-II and some analogues

Anne-Laure Chauvin; Sergey A Nepogodiev; Robert A Field

doi:10.1016/j.carres.2003.09.031

Synthesis of an apiose-containing disaccharide fragment of rhamnogalacturonan-II and some analogues

Carbohydr Res. 2004 Jan 2;339(1):21-7. doi: 10.1016/j.carres.2003.09.031.

Authors

Anne-Laure Chauvin¹, Sergey A Nepogodiev, Robert A Field

Affiliation

¹ Centre for Carbohydrate Chemistry, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, UK.

PMID: 14659667
DOI: 10.1016/j.carres.2003.09.031

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Conformation
Carbohydrate Sequence
Galactose / chemistry
Glycosylation
Isomerism
Molecular Sequence Data
Molecular Structure
Oligosaccharides / chemical synthesis*
Pectins / chemistry*
Pentoses / chemistry*
Rhamnose / chemistry

Substances

Oligosaccharides
Pentoses
rhamnogalacturonan II
Pectins
apiose
Rhamnose
Galactose