We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Expedient Synthesis of the Pentasaccharide Repeating Unit of the Polysaccharide O-Antigen of Escherichia coli O11.
- Authors
Si, Anshupriya; Misra, Anup Kumar
- Abstract
A convergent [3+2] block synthetic strategy was developed for the synthesis of the pentasaccharide repeating unit of the cell wall O-antigen of Escherichia coli O11 strain in excellent yield in a minimum number of steps. Several suitably functionalized thioglycoside derivatives were used as glycosyl donors during the synthesis of the target compound. A thioglycoside was the glycosyl donor used to couple with another thioglycoside derivative in a highly stereoselective manner exploiting the difference of their reactivity profile. A combination of Niodosuccinimide (NIS) and perchloric acid supported over silica gel (HClO4−SiO2) was used as a thiophilic glycosylation activator system in all stereoselective glycosylation reactions. HClO4−SiO2 acted as a user-friendly solid acid catalyst. Yields were very good in all glycosylation steps with a high stereoselective outcome. The synthetic pentasaccharide could be coupled to an appropriate protein to furnish a glycoconjugate derivative for its use in immunochemical studies.
- Subjects
ESCHERICHIA coli; O antigens; MICROBIAL virulence; DIARRHEA; PATHOGENIC microorganisms
- Publication
ChemistryOpen, 2016, Vol 5, Issue 1, p47
- ISSN
2191-1363
- Publication type
Article
- DOI
10.1002/open.201500129