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Total Synthesis of the Repeating Units of <i>Proteus penneri</i> 26 and <i>Proteus vulgaris</i> TG155 via a Common Disaccharide

Ankita Paul, Suvarn S. Kulkarni

2023Organic Letters16 citationsDOI

Abstract

Herein, we report the first total synthesis of the trisaccharide and tetrasaccharide repeating units of P. penneri 26 and P. vulgaris TG155, respectively, having a common disaccharide unit, 3-α- l -Qui p NAc-(1 → 3)-α- d -Glc p NAc-(1 →. Striking features of the targets are the presence of rare sugar units, l -quinovosamine and l -rhamnosamine, all joined through α-glycosidic linkages. Major challenges in the formation of 1,2- cis glycosidic linkages in the case of d -glucosamine, l -quinovosamine, and d -galactosamine have been addressed.

Topics & Concepts

TetrasaccharideDisaccharideChemistryGlycosidic bondTrisaccharideStereochemistryGlucosamineAmino sugarGalactosamineOrganic chemistryPolysaccharideEnzymeCarbohydrate Chemistry and SynthesisGlycosylation and Glycoproteins ResearchLegume Nitrogen Fixing Symbiosis
Total Synthesis of the Repeating Units of <i>Proteus penneri</i> 26 and <i>Proteus vulgaris</i> TG155 via a Common Disaccharide | Litcius