Concise Synthesis of a Pentasaccharide Repeating Unit Corresponding to the O‐Antigen of Salmonella Enterica O51. Issue 3 (24th January 2017)

• Record Type: Journal Article
• Authors: Bhaumik, Ishani; Misra, Anup Kumar
• Is Part Of: ChemistrySelect. Volume 2:Issue 3(2017)
• Page Start: 937
• Page End: 939
• Publication Date: 2017-01-24
• Subjects: antigens -- enteric disease -- glycosylations -- Lipopolysaccharides -- Salmonella enterica; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201601918
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A pentasaccharide repeating unit corresponding to the cell wall O ‐antigen of Salmonella enterica O51 has been synthesized as its 2‐aminoethyl glycoside adopting a sequential stereoselective glycosylation strategy. Judiciously functionalized monosaccharide intermediates were prepared and stereoselectively assembled to get the desired pentasaccharide derivative in excellent yield. An elegant one‐pot reaction condition has been applied for the stereoselective glycosylation and p ‐methoxybenzyl group deprotection. Abstract : Stereoselective glycosylation of suitably protected monosaccharide intermediates furnished a pentasaccharide linked to an aminoethyl linker corresponding to the cell wall O ‐antigen of S. enterica O51, which is responsible for several outbreaks of foodborne illness. Stereoselective glycosylation and removal of p ‐methoxybenzyl protecting group was carried out in a one‐pot reaction condition.