Total Synthesis of a Structurally Complex Tetrasaccharide Repeating Unit of <i>Vibrio cholerae</i> O43
Ankita Paul, Diksha Rai, Kabita Pradhan, Preeti Balhara, Amar Mishra, Suvarn S. Kulkarni
Abstract
Herein we report the first total synthesis of a densely functionalized tetrasaccharide repeating unit of Vibrio cholerae O43, which contains rare deoxy amino sugars d -quinovosamine and d -viosamine attached with the rare amino acid N -acetyl- l -allothreonine. Synthesis of orthogonally protected rare sugars and unnatural amino acid building blocks, stereoselective construction of three consecutive 1,2- cis glycosidic linkages, amide coupling, and the presence of five nitrogen atoms dispersed over four sugar units as well as the carboxylic acid functionality make the total synthesis a formidable task.
Topics & Concepts
TetrasaccharideChemistryVibrio choleraeTotal synthesisAmideGlycosidic bondStereochemistryAmino acidStereoselectivityOrganic chemistryBacteriaCatalysisBiochemistryPolysaccharideEnzymeBiologyGeneticsCarbohydrate Chemistry and SynthesisVibrio bacteria research studiesGlycosylation and Glycoproteins Research