Citation: Kai Zhou, Ao Sun, Yuchao Wang, Hang Dong, Chenkai Bai, Yidian Mo, Xuyang Ding, Xiangbao Meng, Zhongtang Li, Zhongjun Li. Semisynthesis of rare chondroitin sulfate B and T oligosaccharides[J]. Chinese Chemical Letters, ;2025, 36(9): 110783. doi: 10.1016/j.cclet.2024.110783 shu

Semisynthesis of rare chondroitin sulfate B and T oligosaccharides

Kai Zhou ^a ,
Ao Sun ^a ,
Yuchao Wang ^a ,
Hang Dong ^a ,
Chenkai Bai ^a ,
Yidian Mo ^a ,
Xuyang Ding ^a ,
Xiangbao Meng ^a ,
Zhongtang Li ^{a, b, *,} ,
Zhongjun Li ^{a, b, *,}

a.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
b.
Ningbo Institute of Marine Medicine, Peking University, Ningbo 315832, China

lizhongtang@bjmu.edu.cn

zjli@bjmu.edu.cn

Received Date: 23 September 2024
Revised Date: 8 December 2024
Accepted Date: 19 December 2024
Available Online: 19 December 2024

Figures(6)

Chondroitin sulfate (CS) B and T are rare subtypes of CS, which are scare in nature. There are also limited synthetic methods to prepare them. Here we report an ingenious semisynthetic approach to prepare a library of disaccharides, tetrasaccharides and hexasaccharides of CS-B and CS-T based on the acid or enzymatic degradation of natural CS polysaccharide in 9 or 10 steps. Our approach is the shortest synthetic route toward size-defined CS-B and CS-T oligosaccharides reported to date. In addition, a regioselective protection method of hydroxyls is highlighted, which has achieved the regioselective protection of 4 hydroxyl groups among 7 equatorial hydroxyl groups. By preparing size-defined rare CS oligosaccharides from commercially available natural CS polysaccharides, this strategy has the potential to meet the need of rare natural oligosaccharides.
- Chondroitin sulfate,
- Oligosaccharide,
- Semisynthesis,
- Regioselectivity,
- Sulfation,
- Glycosaminoglycan
1. [1]
  H. Wu, R. Zhang, B. Hu, et al., Chin. Chem. Lett. 32 (2021) 3940–3947. doi: 10.1016/j.cclet.2021.04.043
2. [2]
  S. Jalkanen, M. Jalkanen, J. Cell. Biol. 116 (1992) 817–825. doi: 10.1083/jcb.116.3.817
3. [3]
  S. Mizumoto, S. Yamada, K. Sugahara, Curr. Opin. Struct. Biol. 34 (2015) 35–42. doi: 10.1016/j.sbi.2015.06.004
4. [4]
  M.W. Fried, P.E. Duffy, Vaccine 33 (2015) 7483–7488. doi: 10.1016/j.vaccine.2015.10.011
5. [5]
  S. Yamada, K. Sugahara, Curr. Drug. Discov. Technol. 5 (2008) 289–301. doi: 10.2174/157016308786733564
6. [6]
  J.M. Brown, J. Xia, B.Q. Zhuang, et al., Proc. Natl. Acad. Sci. U. S. A. 109 (2012) 4768–4773. doi: 10.1073/pnas.1121318109
7. [7]
  M. Mende, C. Bednarek, M. Wawryszyn, et al., Chem. Rev. 116 (2016) 8193–8255. doi: 10.1021/acs.chemrev.6b00010
8. [8]
  G. Vesssella, S. Traboni, D. Cimini, et al., Biomacromolecules 20 (2019) 3021–3030. doi: 10.1021/acs.biomac.9b00590
9. [9]
  K. Wang, W. Wang, R. Zhang, et al., Food Chem. 434 (2024) 137392. doi: 10.1016/j.foodchem.2023.137392
10. [10]
  S. Nadanka, K. Sugahara, Glycobiology 7 (1997) 253–263. doi: 10.1093/glycob/7.2.253
11. [11]
  N. Takeda, S. Horai, J. Tamura, Carbohydr. Res. 424 (2016) 54–58. doi: 10.1016/j.carres.2016.02.006
12. [12]
  K. Sugahara, Y. Tanaka, S. Yamada, et al., J. Biol. Chem. 271 (1996) 26745–26574. doi: 10.1074/jbc.271.43.26745
13. [13]
  A.K. Shetty, T. Kobayashi, S. Mizumoto, et al., Carbohydr. Res. 344 (2009) 1526–1532. doi: 10.1016/j.carres.2009.02.029
14. [14]
  K. Higashi, Y. Okamoto, A. Mukuno, et al., Carbohydr. Polym. 134 (2015) 557–565. doi: 10.1016/j.carbpol.2015.07.082
15. [15]
  R.S. Cavalcante, A.S. Brito, L.C. Palhares, et al., Carbohydr. Polym. 183 (2018) 192–200. doi: 10.1016/j.carbpol.2017.12.018
16. [16]
  H. Bougatef, F. Krichen, F. Capitani, et al., Carbohydr. Polym. 196 (2018) 272–278. doi: 10.1016/j.carbpol.2018.05.019
17. [17]
  K. Kitazawa, S. Nadanaka, K. Kadomatsu, H. Kitagawa, Commun. Biol. 4 (2021) 114. doi: 10.1038/s42003-020-01618-5
18. [18]
  S. Yang, S. Gigout, A. Molinaro, et al., Mol. Psychiatr. 26 (2021) 5658–5668. doi: 10.1038/s41380-021-01208-9
19. [19]
  C. Spliid, A. Toledo, P. Sanderson, et al., J. Biol. Chem. 297 (2021) 101391. doi: 10.1016/j.jbc.2021.101391
20. [20]
  G. Zhang, Q. Liu, S. Yang, et al., Chin. Chem. Lett. 30 (2019) 686–689. doi: 10.1016/j.cclet.2018.06.012
21. [21]
  K. Wang, F. Bai, X. Zhou, et al., Int. J. Bio. Macromol. 209 (2022) 1280–1287. doi: 10.1364/oe.446015
22. [22]
  Q. Yuan, X. Shi, H. Ma, et al., Int. J. Bio. Macromol. 262 (2024) 129969. doi: 10.1016/j.ijbiomac.2024.129969
23. [23]
  W. Yao, Y. Zhu, X. Zhang, et al., J. Org. Chem. 83 (2018) 14069–14077. doi: 10.1021/acs.joc.8b01987
24. [24]
  Y.S. Chng, G. Tristan, G.W. Yip, Y. Lam, Org. Lett. 21 (2019) 4559–4562. doi: 10.1021/acs.orglett.9b01457
25. [25]
  C. Peng, Q. Wang, R. Jiao, et al., Carbohydr. Polym. 262 (2021) 117911.
26. [26]
  A. Badri, A. Williams, A. Awofiranye, et al., Nat. Commun. 12 (2021) 1389. doi: 10.1038/s41467-021-21692-5
27. [27]
  K. Wang, L. Qi, L. Zhao, et al., Carbohydr. Polym. 301 (2023) 120361. doi: 10.1016/j.carbpol.2022.120361
28. [28]
  J. Li, G. Su, J. Liu, Angew. Chem. Int. Ed. 56 (2017) 11784–11787. doi: 10.1002/anie.201705638
29. [29]
  J. Li, E.M. Sparkenbaugh, G. Su, et al., ACS Cent. Sci. 6 (2020) 1199–1207. doi: 10.1021/acscentsci.0c00712
30. [30]
  P. Lin, Y. Xu, S. Bali, et al., Angew. Chem. Int. Ed. 2024 e202405671. doi: 10.1002/anie.202405671
31. [31]
  M. Wakao, R. Obata, K. Miyachi, et al., Bioorg. Med. Chem. Lett. 25 (2015) 1407–1411. doi: 10.1016/j.bmcl.2015.02.054
32. [32]
  X. Zhang, H. Liu, W. Yao, et al., J. Org. Chem. 84 (2019) 7418–7425. doi: 10.1021/acs.joc.9b00112
33. [33]
  X. Zhang, H. Liu, L. Lin, et al., Angew. Chem. Int. Ed. 57 (2018) 12880–12885. doi: 10.1002/anie.201807546
34. [34]
  C. Lopin, J.C. Jacquinet, Angew. Chem. Int. Ed. 45 (2006) 2574–2578. doi: 10.1002/anie.200503551
35. [35]
  P. Peng, M. Linseis, R.F. Winter, R.R. Schmidt, J. Am. Chem. Soc. 138 (2016) 6002–6009. doi: 10.1021/jacs.6b02454
36. [36]
  T. Li, T. Li, T. Cui, et al., Org. Lett. 20 (2018) 3862–3865. doi: 10.1021/acs.orglett.8b01446
37. [37]
  T. Li, T. Li, M. Linseis, et al., ACS Catal. 10 (2020) 11406–11416. doi: 10.1021/acscatal.0c02112
38. [38]
  T. Li, T. Li, Y. Sun, et al., Org. Chem. Front. 8 (2021) 260–265. doi: 10.1039/d0qo01243b
39. [39]
  J.C. Jacquinet, C. Lopin-Bon, A. Vibert, Chem. Eur. J. 15 (2009) 9579–9595. doi: 10.1002/chem.200900741
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