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We recently mapped the structural epitope of the capsular polysaccharide from type\u2005III Group\u2005B <jats:italic>Streptococcus<\/jats:italic> (GBSIII), a major cause of invasive disease in newborns, by using a dimer fragment (composed of two pentasaccharide repeating units) obtained by depolymerization complexed with a protective mAb. Although reported data had suggested a highly complex epitope contained in a helical structure composed of more than four repeating units, we showed that such dimer conjugated to a carrier protein with a proper glycosylation degree elicited functional antibodies comparably to the full\u2010length conjugated polysaccharide. Here, starting from the X\u2010ray crystallographic structure of the polysaccharide fragment\u2013mAb complex, we synthesized a hexasaccharide comprising exclusively the relevant positions involved in binding. Combining competitive surface plasmon resonance and saturation transfer difference NMR spectroscopy as well as in\u2010silico modeling, we demonstrated that this synthetic glycan was recognized by the mAb similarly to the dimer. The hexasaccharide conjugated to CRM<jats:sub>197<\/jats:sub>, a mutant of diphtheria toxin, elicited a robust functional immune response that was not inferior to the polysaccharide conjugate, indicating that it may suffice as a vaccine antigen. This is the first evidence of an X\u2010ray crystallography\u2010guided design of a synthetic carbohydrate\u2010based conjugate vaccine.<\/jats:p>","DOI":"10.1002\/chem.202000284","type":"journal-article","created":{"date-parts":[[2020,2,14]],"date-time":"2020-02-14T10:50:42Z","timestamp":1581677442000},"page":"7018-7025","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Structure\u2010Guided Design of a Group\u2005B <i>Streptococcus<\/i> Type\u2005III Synthetic Glycan\u2013Conjugate Vaccine"],"prefix":"10.1002","volume":"26","author":[{"given":"Davide","family":"Oldrini","sequence":"first","affiliation":[{"name":"Research Center GlaxoSmithKline Plc  Via Fiorentina 1 53100 Siena Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Linda","family":"del Bino","sequence":"additional","affiliation":[{"name":"Research Center GlaxoSmithKline Plc  Via Fiorentina 1 53100 Siena 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