{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Si A"],"funding":["Council of Scientific and Industrial Research (CSIR), New Delhi, India"],"pagination":["47-50"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC4906483"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["5(1)"],"pubmed_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."],"journal":["ChemistryOpen"],"pubmed_title":["Expedient Synthesis of the Pentasaccharide Repeating Unit of the Polysaccharide O-Antigen of Escherichia coli O11."],"pmcid":["PMC4906483"],"funding_grant_id":["02(0038)/11/EMR-II"],"pubmed_authors":["Si A","Misra AK"],"additional_accession":[]},"is_claimable":false,"name":"Expedient Synthesis of the Pentasaccharide Repeating Unit of the Polysaccharide O-Antigen of Escherichia coli O11.","description":"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.","dates":{"release":"2016-01-01T00:00:00Z","publication":"2016 Feb","modification":"2025-04-19T23:19:26.066Z","creation":"2019-03-27T02:15:58Z"},"accession":"S-EPMC4906483","cross_references":{"pubmed":["27308211"],"doi":["10.1002/open.201500129"]}}