Citation: Lingxin Li, Jing Hu, Chunjun Qin, Juntao Cai, Xiaopeng Zou, Guangzong Tian, Peter H. Seeberger, Jian Yin. Immunological evaluation of the autism-related bacterium Enterocloster bolteae capsular polysaccharide driven by chemical synthesis[J]. Chinese Chemical Letters, ;2025, 36(9): 110797. doi: 10.1016/j.cclet.2024.110797 shu

Immunological evaluation of the autism-related bacterium Enterocloster bolteae capsular polysaccharide driven by chemical synthesis

Lingxin Li ^{a, e, 1} ,
Jing Hu ^{c, e, 1} ,
Chunjun Qin ^{a, e, 1} ,
Juntao Cai ^{a, b} ,
Xiaopeng Zou ^{a, b, e} ,
Guangzong Tian ^{a, b, e} ,
Peter H. Seeberger ^b ,
Jian Yin ^{a, d, e, *,}

a.
School of Biotechnology and Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education, Jiangnan University, Wuxi 214122, China
b.
Biomolecular Systems Department, Max Planck Institute of Colloids and Interfaces, Potsdam 14476, Germany
c.
Wuxi School of Medicine, Jiangnan University, Wuxi 214122, China
d.
School of Life Sciences and Health Engineering, Jiangnan University, Wuxi 214122, China
e.
Innovation Center for Vaccine Engineering, Jiangnan University, Wuxi 214122, China

jianyin@jiangnan.edu.cn

Received Date: 7 November 2024
Revised Date: 22 December 2024
Accepted Date: 23 December 2024
Available Online: 25 December 2024

Figures(8)

The gut pathogen Enterocloster bolteae (E. bolteae) has been associated with autism spectrum disorder (ASD). The development of an E. bolteae vaccine to prevent gastrointestinal diseases, might be beneficial for understanding and treating ASD. Capsular polysaccharide (CPS) is a major virulence factor for E. bolteae. Based on an antigenicity evaluation of oligosaccharides associated with E. bolteae CPS and a structural revision of this carbohydrate antigen, two series of glycans including the d-Manp-d-Rhap type oligosaccharides 13–18 and the d-Ribp-d-Rhap type disaccharides 19–23 related to E. bolteae WAL-16351 CPS were prepared. The hydrogen-bond mediated glycosylation and conformational locking strategy facilitated the constructions of two 1,2-cis-β-glycosidic linkages. Glycan microarray analysis revealed that oligosaccharides 4, 5, and 19 are recognized by antibodies in the anti-E. bolteae sera. The sera IgG antibodies induced by glycoconjugate 19-CRM197 recognize the CPS and bacteria specifically, whereas the IgG antibodies induced respectively by glycoconjugates 4-CRM197 and 5-CRM197 showed almost no binding to the CPS and bacteria. These results indicated that disaccharide 19 is a potential candidate for the development of E. bolteae vaccines.
- Chemical synthesis,
- Enterocloster bolteae,
- Immunology,
- Glycoconjugates,
- Capsular polysaccharide,
- Antibacterial vaccine
1. [1]
  G. Sharon, N.J. Cruz, D.W. Kang, et al., Cell 177 (2019) 1600–1618. doi: 10.1016/j.cell.2019.05.004
2. [2]
  M.J. Maenner, Z. Warren, A.R. Williams, et al., MMWR Surveill Summ. 72 (2023) 1–14. doi: 10.15585/mmwr.ss7202a1
3. [3]
  T. Hirota, B.H. King, JAMA 329 (2023) 157–168. doi: 10.1001/jama.2022.23661
4. [4]
  F. Strati, D. Cavalieri, D. Albanese, et al., Microbiome 5 (2017) 24–34. doi: 10.1186/s40168-017-0242-1
5. [5]
  Y. Wan, T. Zuo, Z. Xu, et al., Gut 71 (2022) 910–918. doi: 10.1136/gutjnl-2020-324015
6. [6]
  K.N. Haas, J.L. Blanchard, Int. J. Syst. Evol. Microbiol. 70 (2020) 23–34. doi: 10.1099/ijsem.0.003698
7. [7]
  Y. Song, C. Liu, D.R. Molitoris, et al., Syst. Appl. Microbiol. 26 (2003) 84–89. doi: 10.1078/072320203322337353
8. [8]
  R.H. Sandler, S.M. Finegold, E.R. Bolte, et al., J. Child Neurol. 15 (2000) 429–435. doi: 10.1177/088307380001500701
9. [9]
  Y.A. Warren, K.L. Tyrrell, D.M. Citron, et al., J. Clin. Microbiol. 44 (2006) 2416–2422. doi: 10.1128/JCM.00116-06
10. [10]
  R. Rohokale, Z. Guo, ACS Infect. Dis. 9 (2023) 178–212. doi: 10.1021/acsinfecdis.2c00559
11. [11]
  F. Boisnard, C. Manson, L. Serradell, et al., Expert Rev. Vaccines 22 (2023) 1196–1213. doi: 10.1080/14760584.2023.2280236
12. [12]
  C. Qin, J. Hu, W. Tong, et al., Chin. J. Nat. Med. 20 (2022) 633–640.
13. [13]
  M. Shirley, Drugs 82 (2022) 989–999. doi: 10.1007/s40265-022-01733-z
14. [14]
  S.R. Parikh, H. Campbell, J.A. Bettinger, et al., J. Infect. 81 (2020) 483–498. doi: 10.1016/j.jinf.2020.05.079
15. [15]
  F. Khatun, I. Toth, R.J. Stephenson, Adv. Drug. Deliv. Rev. 165 (2020) 117–126.
16. [16]
  M. Vella, D. Pace, Expert Opin. Biol. Ther. 15 (2015) 529–546. doi: 10.1517/14712598.2015.993375
17. [17]
  B. Pequegnat, M. Sagermann, M. Valliani, et al., Vaccine 31 (2013) 2787–2790. doi: 10.1016/j.vaccine.2013.04.018
18. [18]
  P.H. Seeberger, Chem. Rev. 121 (2021) 3598–3626. doi: 10.1021/acs.chemrev.0c01210
19. [19]
  G. Tian, J. Hu, C. Qin, et al., J. Am. Chem. Soc. 146 (2024) 18427–18439. doi: 10.1021/jacs.4c03814
20. [20]
  C. Qin, M. Ding, G. Tian, et al., Chin. J. Nat. Med. 20 (2022) 401–420.
21. [21]
  C. Qin, B. Schumann, X. Zou, et al., J. Am. Chem. Soc. 140 (2018) 3120–3127. doi: 10.1021/jacs.8b00148
22. [22]
  C. Qin, H. Hou, M. Ding, et al., Chin. J. Nat. Med. 20 (2022) 387–392.
23. [23]
  Z. Hou, J. Wang, X. Zhang, et al., Chin. Chem. Lett. 34 (2023) 107804. doi: 10.1016/j.cclet.2022.107804
24. [24]
  G. Tian, J. Hu, C. Qin, et al., Angew. Chem. Int. Ed. 59 (2020) 13362–13370. doi: 10.1002/anie.202004267
25. [25]
  X. Zhou, L. Li, Z. Zhang, et al., Angew. Chem. Int. Ed. 61 (2022) e202204420. doi: 10.1002/anie.202204420
26. [26]
  P. Shen, H. Lin, Y. Bao, et al., Chin. Chem. Lett. 34 (2023) 107679. doi: 10.1016/j.cclet.2022.07.022
27. [27]
  J. Sianturi, P. Priegue, J. Hu, et al., Angew. Chem. Int. Ed. 61 (2022) e202209556. doi: 10.1002/anie.202209556
28. [28]
  C. Qin, L. Li, G. Tian, et al., J. Am. Chem. Soc. 144 (2022) 21068–21079. doi: 10.1021/jacs.2c05953
29. [29]
  N.W. Frame, M.J. Allas, B. Pequegnat, et al., Carbohydr. Res. 526 (2023) 108805. doi: 10.1016/j.carres.2023.108805
30. [30]
  B. Pequegnat, M.A. Monteiro, Curr. Med. Chem. 26 (2019) 6341–6348. doi: 10.2174/0929867326666190225164527
31. [31]
  J. Davidson, C. Gauthier-Signore, K.P. Bishop, et al., Org. Biomol. Chem. 20 (2022) 2964–2980. doi: 10.1039/d2ob00131d
32. [32]
  J. Cai, J. Hu, C. Qin, et al., Angew. Chem. Int. Ed. 59 (2020) 20529–20537. doi: 10.1002/anie.202007209
33. [33]
  M. Zhao, G. Tian, C. Qin, et al., Chin. J. Chem. 42 (2024) 243–251. doi: 10.1002/cjoc.202300510
34. [34]
  B. Schumann, H.S. Hahm, S.G. Parameswarappa, et al., Sci. Transl. Med. 9 (2017) eaaf5347. doi: 10.1126/scitranslmed.aaf5347
35. [35]
  D. Crich, Q. Yao, J. Am. Chem. Soc. 126 (2004) 8232–8236. doi: 10.1021/ja048070j
36. [36]
  J. Cai, X. Yuan, Y. Kong, et al., Chin. J. Nat. Med. 21 (2023) 886–901.
37. [37]
  X. Liu, Y. Lin, W. Peng, et al., Angew. Chem. Int. Ed. 61 (2022) e202206128. doi: 10.1002/anie.202206128
38. [38]
  B. Yu, H. Tao, Tetrahedron Lett. 42 (2001) 2405–2407. doi: 10.1016/S0040-4039(01)00157-5
39. [39]
  A. Imamura, T. Lowary, Trends Glycosci. Glycotechnol. 23 (2011) 134–152. doi: 10.4052/tigg.23.134
40. [40]
  X. Zou, J. Hu, M. Zhao, et al., J. Am. Chem. Soc. 144 (2022) 14535–14547. doi: 10.1021/jacs.2c03068
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  Xueling Yu , Lixing Fu , Tong Wang , Zhixin Liu , Na Niu , Ligang Chen . Multivariate chemical analysis: From sensors to sensor arrays. Chinese Chemical Letters, 2024, 35(7): 109167-. doi: 10.1016/j.cclet.2023.109167
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沈阳化工大学材料科学与工程学院沈阳 110142