Abstract
The synthesis of two protected tetrasaccharide pentenyl glycosides with diarabinan and digalactan branching related to the pectic polysaccharide rhamnogalacturonan I is reported. The strategy relies on the coupling of N-phenyl trifluoroacetimidate disaccharide donors to a common rhamnosyl acceptor. The resulting trisaccharide thioglycosides were finally coupled to an n-pentenyl galactoside acceptor to access the two protected branched tetrasaccharides.
Highlights
Pectins are the most structurally complex polysaccharides found in plant cell walls
To the best of our knowledge, except for the synthesis of tri- and tetrasaccharide building blocks containing a single galactose unit as a side chain by Vogel and co-workers [10,11], branched Rhamnogalacturonan I (RG-I) fragments have not previously been addressed by chemical synthesis [12]. These structures are of great interest because they are useful for the study of pectin and the enzymes involved in both the biosynthesis and degradation of RG-I [1,2,7,13,14]
We report the synthesis of two protected tetrasaccharides with diarabinan and digalactan branching, designed for the assembly of larger RG-I oligosaccharides
Summary
Pectins are the most structurally complex polysaccharides found in plant cell walls. These highly heterogeneous polysaccharides are fundamental components of the primary cell wall of plants where they modulate plant cell functions such as support, defense, signaling, and cell adhesion [1,2].They play a vital role in the food industry, serving as stabilizing and thickening agents in products such as jams, yogurt, and jellies [3]. To the best of our knowledge, except for the synthesis of tri- and tetrasaccharide building blocks containing a single galactose unit as a side chain by Vogel and co-workers [10,11], branched RG-I fragments have not previously been addressed by chemical synthesis [12]. These structures are of great interest because they are useful for the study of pectin and the enzymes involved in both the biosynthesis and degradation of RG-I [1,2,7,13,14]. We report the synthesis of two protected tetrasaccharides with diarabinan and digalactan branching, designed for the assembly of larger RG-I oligosaccharides
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