Approaches to Chemical Synthesis of Pectic Oligosaccharides

S.A. Nepogodiev, R.A. Field, I. Damager

Research output: Chapter in Book/Report/Conference proceedingChapterpeer-review

Abstract

Many aspects of pectin biosynthesis and the physical properties of pectic polysaccharides can be better understood with the aid of small, well‐defined oligosaccharide fragments of these macromolecules. Synthetic chemists have contributed to the study of pectin by preparation of fragments representing all three major types of pectic polysaccharide: homogalacturonan (HG), rhamnogalacturonan‐I (RG‐I) and rhamnogalacturonan‐II (RG‐II).

Such molecules have been synthesized by sequential coupling of building blocks, the so‐called glycosyl donors (GD) and glycosyl acceptors (GA), which aimed at the formation of specific glycosidic linkages as they are present in the target oligosaccharides. Challenges in synthesis of pectic oligosaccharides are associated with often poor stereoselectivity of glycosylation reactions between GA and GD, in particular for the construction of 1,2‐cis‐glycosidic linkages, high degrees of branching of oligosaccharide chains of target molecules and the nature of many monosaccharide components of pectin, which are often acidic and sometimes rare branched‐chain sugars. Preparation of carbohydrate building blocks, including de novo syntheses of unusual sugars, protecting group strategies for GA and GD, glycosylation methodologies and general strategies for oligosaccharide assembly are described with the focus on pectin fragments. Synthetic routes to fragments of each type of pectic polysaccharides are discussed in detail in separate sections and structures of all currently known synthetic pectin fragments are summarized. The unsolved problems and future prospects for improved access to synthetic pectin fragments are also discussed.
Original languageUndefined
Title of host publicationAnnual Plant Reviews
Subtitle of host publicationPlant Polysaccharides, Biosynthesis and Bioengineering
EditorsPeter Ulvskov
PublisherJohn Wiley & Sons Ltd
Chapter3
Pages65-92
Number of pages28
ISBN (Electronic)9781444391015
ISBN (Print)9781405181723
DOIs
Publication statusPublished - 2011

Publication series

NameAnnual Plant Reviews
Volume41

Research Beacons, Institutes and Platforms

  • Manchester Institute of Biotechnology

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