title: Synthesis of the tetrasaccharide repeating unit of the O-glycan from the polar flagellum flagellin of Azospirillum brasilense Sp7.
abstract: Chemical synthesis of the tetrasaccharide repeating unit of the O-glycan from the polar flagellum flagellin of Azospirillum brasilense Sp7 in the form of its p-methoxyphenyl glycoside is reported. The required glycosidic linkages have been accomplished by activation of thioglycosides with N-iodosuccinimide in the presence of H2SO4-silica. H2SO4-silica was found to be an effective alternative to the classical acid promoters like TfOH or TMSOTf and it can lead to the formation of both 1,2-cis and 1,2-trans glycosidic linkages depending on the protecting group manipulation and control of the reaction condition.
authors.affiliation: Indian Institute of Science Education and Research (IISER) Kolkata, Mohanpur 741246, India.
authors.forename: Kumar Bhaskar
authors.initials: KB
authors.lastname: Pal
authors.affiliation: Indian Institute of Science Education and Research (IISER) Kolkata, Mohanpur 741246, India. Electronic address: sugarnet73@hotmail.com.
authors.forename: Balaram
authors.initials: B
authors.lastname: Mukhopadhyay
mesh_terms: D015806:Azospirillum brasilense / Q000737:chemistry*; D005407:Flagella / Q000737:chemistry; D005408:Flagellin / Q000737:chemistry*; D019081:O Antigens / Q000737:chemistry / Q000235:genetics; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D011134:Polysaccharides / Q000737:chemistry*; D011401:Promoter Regions, Genetic; D012822:Silicon Dioxide / Q000737:chemistry; D013388:Succinimides / Q000737:chemistry
chemical_list: D019081:O Antigens; D009844:Oligosaccharides; D011134:Polysaccharides; D013388:Succinimides; D005408:Flagellin; C008155:N-iodosuccinimide; D012822:Silicon Dioxide
keywords: Flagellin O-glycan; H(2)SO(4)–silica; Total synthesis