Chemoenzymatic Synthesis and Antigenicity Evaluation of an O-Antigen Octadecasaccharide from Helicobacter pylori
文献类型：期刊论文
| 作者 | Liu, Wei2; Zhang, Wei1,2; Xu, Zhuojia2; Liu, Wenkai2,4; Wang, Jiajia4; Li, Xia4; Gao, Jian3; Li, Tiehai1,2 |
| 刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
 |
| 出版日期 | 2026-01-08 |
| 页码 | 10 |
| 关键词 | Antigenicity evaluation Bacterial oligosaccharides Carbohydrates Chemoenzymatic synthesis Glycosylation |
| ISSN号 | 1433-7851 |
| DOI | 10.1002/anie.202523768 |
| 通讯作者 | Li, Tiehai(tiehaili@simm.ac.cn) |
| 英文摘要 | Helicobacter pylori infection represents a major global health challenge, characterized by high prevalence, significant association with gastric cancer, and rising antibiotic resistance. Carbohydrate-based vaccines targeting the O-antigen of lipopolysaccharide (LPS) present a promising alternative to conventional antimicrobial therapies. To explore the immunogenicity of LPS O-antigen from clinical isolate H. pylori SS1, we report an integrated chemoenzymatic strategy for the first synthesis of its octadecasaccharide O-antigen and related fragments for antigenicity evaluation. Our strategy features modular chemical synthesis of a decasaccharide precursor containing a high-carbon sugar (D,D-Hep) residue, a unique oligomeric beta 1,2-linked ribofuranosyl tetrasaccharide motif and a switchable glucosamine (GlcNH2) residue through stereoconvergent [6 + 4] assembly, followed by protecting-group-controlled enzymatic elongation to precisely install hybrid Lewis antigen moiety (Ley-Lex) in a site-specific fucosylation manner to afford the target octadecasaccharide bearing five challenging 1,2-cis-glycosidic linkages. Chemical stereoselective construction of 1,2-cis-glucosidic and 1,2-cis-fucosidic linkages was accomplished by reagent-controlled glycosylation and 4-O-acyl remote participation, respectively. Enzymatic site-specific installation of the remaining three 1,2-cis-fucosidic linkages was achieved using two robust fucosyltransferases and a strategically designed GlcNH2 residue. Glycan microarray-based screening of the synthetic O-antigen and its subunits with H. pylori-infected patient sera identified an undecasaccharide as a simpler and key epitope for vaccine development. |
| WOS关键词 | LIPOPOLYSACCHARIDE STRUCTURE ; BINDING SPECIFICITIES ; CARBOHYDRATE VACCINES ; CHEMICAL-SYNTHESIS ; GLYCOSYL ; GLYCANS ; ALKYNYLBENZOATES ; STRATEGIES ; LECTINS ; ENZYMES |
| 资助项目 | Science and Technology Commission of Shanghai Municipality[24YF2755000] ; National Natural Science Foundation of China[22377134] ; National Natural Science Foundation of China[22177060] ; Strategic Priority Research Program of CAS[XDB1060000] ; NMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate-Based Medicine[2023QRECM03] ; Shanghai Municipal Science and Technology Major Project |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:001656777100001 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/322551]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Li, Tiehai |
| 作者单位 | 1.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Chem Biol, Shanghai 201203, Peoples R China 3.Shandong Univ, Natl Glycoengn Res Ctr, Qingdao 266237, Peoples R China 4.Henan Univ, Sch Med, Inst Joint Natl Lab Antibody Drug Engn, Kaifeng 475004, Peoples R China |
| 推荐引用方式 GB/T 7714 | Liu, Wei,Zhang, Wei,Xu, Zhuojia,et al. Chemoenzymatic Synthesis and Antigenicity Evaluation of an O-Antigen Octadecasaccharide from Helicobacter pylori[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2026:10. |
| APA | Liu, Wei.,Zhang, Wei.,Xu, Zhuojia.,Liu, Wenkai.,Wang, Jiajia.,...&Li, Tiehai.(2026).Chemoenzymatic Synthesis and Antigenicity Evaluation of an O-Antigen Octadecasaccharide from Helicobacter pylori.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,10. |
| MLA | Liu, Wei,et al."Chemoenzymatic Synthesis and Antigenicity Evaluation of an O-Antigen Octadecasaccharide from Helicobacter pylori".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2026):10. |
入库方式： OAI收割
来源：上海药物研究所
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