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

Anne-Laure Chauvin, Sergey A. Nepogodiev, Robert A. Field

School of Chemistry, Pharmacy and Pharmacology

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

Abstract

β-Rhamnosylation of methyl 2-C-hydroxymethyl-2,3-O-isopropylidene- β-D-erythrofuranoside and methyl 2,3-O-isopropylidene-β-D- ribofuranoside was achieved using 4-O-acetyl-2,3-O-carbonyl-α-L- rhamnopyranosyl bromide and Ag₂O as a promoter. Deprotected disaccharides β-L-Rhap-(1→3^′)-β-D-Apif-OMe and β-L-Rhap-(1→3^′)-β-D-Ribf-OMe were compared to their α-rhamnosyl isomers which were prepared using conventional Helferich glycosylation.

Original language	English
Pages (from-to)	21-27
Number of pages	7
Journal	Carbohydrate Research
Volume	339
Issue number	1
Early online date	24 Oct 2003
DOIs	https://doi.org/10.1016/j.carres.2003.09.031
Publication status	Published - 2 Jan 2004

Keywords

Cell walls
Higher plants
Pectins

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10.1016/j.carres.2003.09.031

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title = "Synthesis of an apiose-containing disaccharide fragment of rhamnogalacturonan-II and some analogues",

abstract = "β-Rhamnosylation of methyl 2-C-hydroxymethyl-2,3-O-isopropylidene- β-D-erythrofuranoside and methyl 2,3-O-isopropylidene-β-D- ribofuranoside was achieved using 4-O-acetyl-2,3-O-carbonyl-α-L- rhamnopyranosyl bromide and Ag2O as a promoter. Deprotected disaccharides β-L-Rhap-(1→3′)-β-D-Apif-OMe and β-L-Rhap-(1→3′)-β-D-Ribf-OMe were compared to their α-rhamnosyl isomers which were prepared using conventional Helferich glycosylation.",

keywords = "Cell walls, Higher plants, Pectins",

author = "Anne-Laure Chauvin and Nepogodiev, {Sergey A.} and Field, {Robert A.}",

note = "Funding Information: This research was supported by the Weston Foundation and the Biotechnology and Biological Sciences Research Council in the UK. ",

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AU - Chauvin, Anne-Laure

AU - Nepogodiev, Sergey A.

AU - Field, Robert A.

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AB - β-Rhamnosylation of methyl 2-C-hydroxymethyl-2,3-O-isopropylidene- β-D-erythrofuranoside and methyl 2,3-O-isopropylidene-β-D- ribofuranoside was achieved using 4-O-acetyl-2,3-O-carbonyl-α-L- rhamnopyranosyl bromide and Ag2O as a promoter. Deprotected disaccharides β-L-Rhap-(1→3′)-β-D-Apif-OMe and β-L-Rhap-(1→3′)-β-D-Ribf-OMe were compared to their α-rhamnosyl isomers which were prepared using conventional Helferich glycosylation.

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KW - Pectins

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

Abstract

Keywords

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