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Carbohydrate\u2010based vaccines targeting the O\u2010antigen of lipopolysaccharide (LPS) present a promising alternative to conventional antimicrobial therapies. To explore the immunogenicity of LPS O\u2010antigen from clinical isolate\n                    <jats:italic>H. pylori<\/jats:italic>\n                    SS1, we report an integrated chemoenzymatic strategy for the first synthesis of its octadecasaccharide O\u2010antigen and related fragments for antigenicity evaluation. Our strategy features modular chemical synthesis of a decasaccharide precursor containing a high\u2010carbon sugar (D,D\u2010Hep) residue, a unique oligomeric \u03b21,2\u2010linked ribofuranosyl tetrasaccharide motif and a switchable glucosamine (GlcNH\n                    <jats:sub>2<\/jats:sub>\n                    ) residue through stereoconvergent [6\u00a0+\u00a04] assembly, followed by protecting\u2010group\u2010controlled enzymatic elongation to precisely install hybrid Lewis antigen moiety (Le\n                    <jats:italic>\n                      <jats:sup>y<\/jats:sup>\n                    <\/jats:italic>\n                    \u2010Le\n                    <jats:italic>\n                      <jats:sup>x<\/jats:sup>\n                    <\/jats:italic>\n                    ) in a site\u2010specific fucosylation manner to afford the target octadecasaccharide bearing five challenging 1,2\u2010\n                    <jats:italic>cis<\/jats:italic>\n                    \u2010glycosidic linkages. Chemical stereoselective construction of 1,2\u2010\n                    <jats:italic>cis<\/jats:italic>\n                    \u2010glucosidic and 1,2\u2010\n                    <jats:italic>cis<\/jats:italic>\n                    \u2010fucosidic linkages was accomplished by reagent\u2010controlled glycosylation and 4\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010acyl remote participation, respectively. Enzymatic site\u2010specific installation of the remaining three 1,2\u2010\n                    <jats:italic>cis<\/jats:italic>\n                    \u2010fucosidic linkages was achieved using two robust fucosyltransferases and a strategically designed GlcNH\n                    <jats:sub>2<\/jats:sub>\n                    residue. Glycan microarray\u2010based screening of the synthetic O\u2010antigen and its subunits with\n                    <jats:italic>H. pylori<\/jats:italic>\n                    \u2010infected patient sera identified an undecasaccharide as a simpler and key epitope for vaccine development.\n                  <\/jats:p>","DOI":"10.1002\/anie.202523768","type":"journal-article","created":{"date-parts":[[2026,1,9]],"date-time":"2026-01-09T05:30:34Z","timestamp":1767936634000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Chemoenzymatic Synthesis and Antigenicity Evaluation of an O\u2010Antigen Octadecasaccharide from\n                    <i>Helicobacter pylori<\/i>"],"prefix":"10.1002","volume":"65","author":[{"given":"Wei","family":"Liu","sequence":"first","affiliation":[{"name":"State Key Laboratory of Chemical Biology Shanghai Institute of Materia Medica, Chinese Academy of Sciences  Shanghai 201203 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wei","family":"Zhang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemical Biology Shanghai Institute of Materia Medica, Chinese Academy of Sciences  Shanghai 201203 China"},{"name":"School of Chinese Materia Medica Nanjing University of Chinese Medicine  Nanjing 210023 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhuojia","family":"Xu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemical Biology Shanghai Institute of Materia Medica, Chinese Academy of Sciences  Shanghai 201203 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenkai","family":"Liu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemical Biology Shanghai Institute of Materia Medica, Chinese Academy of Sciences  Shanghai 201203 China"},{"name":"Institutes Joint National Laboratory for Antibody Drug Engineering School of Medicine Henan University  Kaifeng 475004 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiajia","family":"Wang","sequence":"additional","affiliation":[{"name":"Institutes Joint National Laboratory for Antibody Drug Engineering School of Medicine Henan University  Kaifeng 475004 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xia","family":"Li","sequence":"additional","affiliation":[{"name":"Institutes Joint National Laboratory for Antibody Drug Engineering School of Medicine Henan University  Kaifeng 475004 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jian","family":"Gao","sequence":"additional","affiliation":[{"name":"National Glycoengineering Research Center Shandong University  Qingdao 266237 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3600-1828","authenticated-orcid":false,"given":"Tiehai","family":"Li","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemical Biology Shanghai Institute of Materia Medica, Chinese Academy of Sciences  Shanghai 201203 China"},{"name":"School of Chinese Materia Medica Nanjing University of Chinese Medicine  Nanjing 210023 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,1,8]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41572\u2010023\u201000431\u20108"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrmicro3016"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/S2468\u20101253(23)00070\u20105"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrc2857"},{"key":"e_1_2_7_5_1","first-page":"1","volume":"61","author":"Schistosomes, liver flukes and Helicobacter pylori","year":"1994","journal-title":"IARC Monogr. 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