Synthesis of branched oligosaccharides related to the pectic rhamnogalacturonan i polysaccharide

<none>

Programme Social programme Plenary speakers Keynote speakers 1st EuroCarb Young Researcher (ECYR) Workshop CarboMet Workshop Mini symposium: Glycobiology at the LUMC and beyond Favourites/Agenda

Social programme

Plenary speakers

Keynote speakers

1st EuroCarb Young Researcher (ECYR) Workshop

CarboMet Workshop

Mini symposium: Glycobiology at the LUMC and beyond

Favourites/Agenda

Photos

Venue & Travel Venue Accommodation City of Leiden Travel directions

Venue

Accommodation

City of Leiden

Travel directions

Committees

Home

Synthesis of branched oligosaccharides related to the pectic rhamnogalacturonan i polysaccharide

Cecilia Romanò 1 , Shahid I. Awan 1 , Mads H. Clausen 1

1 Center for Nanomedicine and Theranostics, Department of Chemistry, Technical University Of Denmark, Kgs. Lyngby, Denmark

Pectin is one of the major plant cell wall components. It is constituted by highly complex and heterogeneous polysaccharides, which contribute to the modulation of several physiological processes such as cell growth and differentiation, cell-cell adhesion and cell wall support, and defense mechanisms.[1,2] Rhamnogalacturonan I (RG-I) is one of the structural domains of pectic polysaccharides, along with homogalacturonan, rhamnogalacturonan II, xylogalacturonan, and apiogalacturonan. Structurally diverse and complex, RG-I polysaccharides have a backbone consisting of [→2)-α-L-Rhap-(1→4)-α-D-GalA-(1→] disaccharide repeats, with numerous branching side-chains of galactans, arabinans, or arabinogalactans, generally found at the C-4 position of L-rhamnose residues.[3]

Given the structural complexity of RG-I polysaccharides, well-defined synthetic RG-I related oligosaccharides are necessary for investigating enzymes involved in pectin biosynthesis and degradation, as well as for aiding structural analyses of the peptic polysaccharides. While several syntheses of fragments corresponding to the RG-I backbone have been described, the chemical synthesis of large structures with a branched backbone have not been previously reported.[4] Herein, we present our most recent results on the synthesis of a RG-I heptasaccharide backbone by means of a [4+3] glycosylation and late-stage oxidation approach, and the installation of galactan side-chains of different lengths to furnish novel branched RG-I fragments (Figure 1).

Figure 1: Branched-backbone RG-I fragments

Mohnen, D. Pectin Structure and Biosynthesis. Curr. Opin. Plant Biol. 2008, 11 (3), 266–277.

Voragen, A. G. J.; Coenen, G. J.; Verhoef, R. P.; Schols, H. A. Pectin, a Versatile Polysaccharide Present in Plant Cell Walls. Struct. Chem. 2009, 20 (2), 263–275.

Yapo, B. M. Rhamnogalacturonan-I: A Structurally Puzzling and Functionally Versatile Polysaccharide from Plant Cell Walls and Mucilages. Polym. Rev. 2011, 51 (4), 391–413.

Kinnaert, C.; Daugaard, M.; Nami, F.; Clausen, M. H. Chemical Synthesis of Oligosaccharides Related to the Cell Walls of Plants and Algae. Chem. Rev. 2017, 117 (17), 11337–11405.

Contact eurocarb@eurocarb2019.com for general questions about EUROCARB2019, or codee@eurocarb2019.com for scientific questions.

Leiden University / Leiden Institute of Chemistry lic.leidenuniv.nl

European Carbohydrate Organisation

Congress by Design www.congressbydesign.com