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Synthesis of selectively protected α-(1→3)- and α-(1→5)-linked octasaccharide moiety bearing a Janus aglycone, related to the branching site of mycobacterial polysaccharides

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Abstract

A novel selectively protected α-(1→3)- and α-(1→5)-linked branched octasaccharide based on arabinofuranose was synthesized via a convergent route as a glycoside with 4-(2-chloroethoxy)phenyl aglycone, belonging to the class of Janus aglycones. The obtained octasaccharide is related to the branching site of lipoarabinomannan and arabinogalactan of mycobacteria. The Janus aglycone moiety can play the role of not only a temporary protective group at the anomeric position of sugar, but also a pre-spacer for the synthesis of neoglycoconjugates useful in the design of new tools for diagnostics of tuberculosis.

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References

  1. World Health Organization. Tuberculosis Fact Sheet; https://www.who.int/en/news-room/fact-sheets/detail/tuberculosis (accessed June 23, 2022).

  2. W. F. Paolo, J. D. Nosanchuk, Lancet Infect. Dis., 2004, 4, 287–293; DOI: https://doi.org/10.1016/s1473-3099(04)01004-7.

    Article  PubMed  Google Scholar 

  3. P. D. O. Davies, Ann. Med., 2009, 35, 235–243; DOI: https://doi.org/10.1080/07853890310005713.

    Article  Google Scholar 

  4. B. Hamasur, G. Ka, S. B. Svenson, Vaccine, 1999, 17, 2853–2861.

    Article  CAS  PubMed  Google Scholar 

  5. H.-S. Kim, E. S. M. Ng, R. B. Zheng, R. M. Whittal, D. C. Schriemer, T. L. Lowary, in Carbohydrate-Based Vaccines, Ed. R. Roy, American Chemical Society, 2008, p. 184–198.

  6. R. B. Zheng, S. A. F. Jegouzo, M. Joe, Y. Bai, H. A. Tran, K. Shen, J. Saupe, L. Xia, M. F. Ahmed, Y. H. Liu, P. S. Patil, A. Tripathi, S. C. Hung, M. E. Taylor, T. L. Lowary, K. Drickamer, ACS Chem. Biol., 2017, 12, 2990–3002; DOI: https://doi.org/10.1021/acschembio.7b00797.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Z. H. Li, T. Bavaro, S. Tengattini, R. Bernardini, M. Mattei, F. Annunziata, R. B. Cole, C. P. Zheng, M. Sollogoub, L. Tamborini, M. Terreni, Y. M. Zhang, Eur. J. Med. Chem., 2020, 204, 112578; DOI: https://doi.org/10.1016/j.ejmech.2020.112578.

    Article  CAS  PubMed  Google Scholar 

  8. T. T. Chen, C. Blanc, Y. Y. Liu, E. Ishida, S. Singer, J. Y. Xu, M. Joe, E. R. Jenny-Avital, J. Chan, T. L. Lowary, J. M. Achkar, J. Clin. Invest., 2020, 130, 1808–1822; DOI: https://doi.org/10.1172/jci128459.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. P. I. Abronina, N. M. Podvalnyy, T. M. Mel’nikova, A. I. Zinin, K. G. Fedina, V. V. Kachala, V. I. Torgov, L. O. Kononov, E. A. Panfertsev, E. V. Baranova, V. V. Mochalov, V. I. Dyatlova, S. F. Biketov, Russ. Chem. Bull., 2010, 59, 2333–2337; DOI: https://doi.org/10.1007/s11172-010-0397-4.

    Article  CAS  Google Scholar 

  10. V. I. Dyatlova, P. I. Abronina, A. G. Bogun, L. O. Kononov, T. M. Mel’nikova, V. V. Mochalov, Ye. A. Panfertsev, N. M. Podvalnyy, S. F. Biketov, Biotekhnologiya [Biotechnology], 2013, 78–86 (in Russian).

  11. A. G. Korolyova-Ushakova, E. V. Baranova, S. G. Ignatov, P. V. Soloviev, N. N. Kondakov, T. M. Mel’nikova, P. I. Abronina, N. M. Podval’niy, L. O. Kononov, S. F. Biketov, Appl. Biochem. Microbiol., 2019, 55, 696–703; DOI: https://doi.org/10.1134/S0003683819060097.

    Article  CAS  Google Scholar 

  12. A. G. Korolyova-Ushakova, E. V. Baranova, S. G. Ignatov, P. V. Solov’ev, S. F. Biketov, P. I. Abronina, N. N. Kondakov, T. M. Mel’nikova, L. O. Kononov, L. V. Saroyantc, V. Z. Naumov, V. V. Duyko, Infekc. bolezni [Infectious Diseases], 2020, 18, 164–168; DOI: https://doi.org/10.20953/1729-9225-2020-4-164-168.

    Article  Google Scholar 

  13. G. L. Burygin, P. I. Abronina, N. M. Podvalnyy, S. A. Staroverov, L. O. Kononov, L. A. Dykman, Beilstein J. Nanotechnol., 2020, 11, 480–493; DOI: https://doi.org/10.3762/bjnano.11.39.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. T. L. Lowary, Acc. Chem. Res., 2016, 49, 1379–88; DOI: https://doi.org/10.1021/acs.accounts.6b00164.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. L. Wang, Z. Guo, J. Carbohydr. Chem., 2019, 38, 269–334; DOI: https://doi.org/10.1080/07328303.2019.1630839.

    Article  CAS  Google Scholar 

  16. L. Han, L. Wang, Z. Guo, J. Carbohydr. Chem., 2019, 38, 335–382; DOI: https://doi.org/10.1080/07328303.2019.1630840.

    Article  CAS  Google Scholar 

  17. K. Liu, L. Wang, Z. Guo, J. Carbohydr. Chem., 2019, 38, 414–469; DOI: https://doi.org/10.1080/07328303.2019.1630841.

    Article  CAS  Google Scholar 

  18. R. P. Sweeney, T. L. Lowary, in Comprehensive Glycoscience, Eds J. J. Barchi, S. Vidal, Elsevier, Amsterdam, 2021, p. 267–285.

  19. P. I. Abronina, N. M. Podval’niy, L. O. Kononov, Russ. Chem. Bull., 2022, 71, 6–29; DOI: https://doi.org/10.1007/s11172-022-3371-z.

    Article  CAS  Google Scholar 

  20. N. N. Kondakov, T. M. Mel’nikova, A. I. Zinin, V. I. Torgov, A. O. Chizhov, E. A. Gordeeva, N. V. Bovin, L. O. Kononov, Russ. Chem. Bull., 2014, 63, 501–506; DOI: https://doi.org/10.1007/s11172-014-0460-7.

    Article  CAS  Google Scholar 

  21. P. I. Abronina, K. G. Fedina, N. M. Podvalnyy, A. I. Zinin, A. O. Chizhov, N. N. Kondakov, V. I. Torgov, L. O. Kononov, Carbohydr. Res., 2014, 396, 25–36; DOI: https://doi.org/10.1016/j.carres.2014.05.017.

    Article  CAS  PubMed  Google Scholar 

  22. P. I. Abronina, A. I. Zinin, D. A. Romashin, N. N. Malysheva, A. O. Chizhov, L. O. Kononov, Synlett, 2015, 26, 2267–2271; DOI: https://doi.org/10.1055/s-0035-1560172.

    Article  CAS  Google Scholar 

  23. N. N. Kondakov, T. M. Mel’nikova, T. V. Chekryzhova, M. V. Mel’nikova, A. I. Zinin, V. I. Torgov, A. O. Chizhov, L. O. Kononov, Russ. Chem. Bull., 2015, 64, 1142–1148; DOI: https://doi.org/10.1007/s11172-015-0991-6.

    Article  CAS  Google Scholar 

  24. P. I. Abronina, A. I. Zinin, N. N. Malysheva, E. V. Stepanova, A. O. Chizhov, V. I. Torgov, L. O. Kononov, Synlett, 2017, 28, 1608–1613; DOI: https://doi.org/10.1055/s-0036-1589028.

    Article  CAS  Google Scholar 

  25. P. I. Abronina, A. I. Zinin, D. A. Romashin, V. V. Tereshina, A. O. Chizhov, L. O. Kononov, Carbohydr. Res., 2018, 464, 28–43; DOI: https://doi.org/10.1016/j.carres.2018.05.005.

    Article  CAS  PubMed  Google Scholar 

  26. M. V. Panova, N. M. Podvalnyy, E. L. Okun, P. I. Abronina, A. O. Chizhov, L. O. Kononov, Carbohydr. Res., 2018, 456, 35–44; DOI: https://doi.org/10.1016/j.carres.2017.11.002.

    Article  CAS  PubMed  Google Scholar 

  27. E. V. Stepanova, N. M. Podvalnyy, P. I. Abronina, L. O. Kononov, Synlett, 2018, 29, 2043–2045; DOI: https://doi.org/10.1055/s-0037-1610648.

    Article  CAS  Google Scholar 

  28. E. V. Stepanova, P. I. Abronina, A. I. Zinin, A. O. Chizhov, L. O. Kononov, Carbohydr. Res., 2019, 471, 95–104; DOI: https://doi.org/10.1016/j.carres.2018.11.013.

    Article  CAS  PubMed  Google Scholar 

  29. N. N. Kondakov, M. V. Panova, P. I. Abronina, A. I. Zinin, A. M. Shpirt, L. O. Kononov, Russ. Chem. Bull., 2019, 68, 416–423; DOI: https://doi.org/10.1007/s11172-019-2402-x.

    Article  CAS  Google Scholar 

  30. P. Abronina, A. Zinin, A. Chizhov, L. Kononov, Eur. J. Org. Chem., 2020, 4146–4160; DOI: https://doi.org/10.1002/ejoc.202000520.

  31. E. V. Stepanova, A. I. Zinin, P. I. Abronina, A. O. Chizhov, L. O. Kononov, Synlett, 2020, 31, 1491–1496; DOI: https://doi.org/10.1055/s-0040-1707137.

    Article  Google Scholar 

  32. P. I. Abronina, N. N. Malysheva, A. I. Zinin, M. Y. Karpenko, N. G. Kolotyrkina, L. O. Kononov, Synlett, 2022, 33, 473–477; DOI: https://doi.org/10.1055/a-1730-9458.

    Article  CAS  Google Scholar 

  33. I. V. Myachin, Z. Z. Mamirgova, E. V. Stepanova, A. I. Zinin, A. O. Chizhov, L. Kononov, Eur. J. Org. Chem., 2022, e202101377; DOI: https://doi.org/10.1002/ejoc.202101377.

  34. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem., Int. Ed., 2001, 40, 2004–2021; DOI: https://doi.org/10.1002/1521-3773(20010601)40:11<2004::Aid-anie2004>3.0.Co;2-5.

    Article  CAS  Google Scholar 

  35. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem., Int. Ed., 2002, 41, 2596–2599; DOI: https://doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4.

    Article  CAS  Google Scholar 

  36. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem., 2002, 67, 3057–3064; DOI: https://doi.org/10.1021/jo011148j.

    Article  PubMed  Google Scholar 

  37. S. Dedola, S. A. Nepogodiev, R. A. Field, Org. Biomol. Chem., 2007, 5, 1006–1017; DOI: https://doi.org/10.1039/b618048p.

    Article  CAS  PubMed  Google Scholar 

  38. M. Meldal, C. W. Tornøe, Chem. Rev., 2008, 108, 2952–3015; DOI: https://doi.org/10.1021/cr0783479.

    Article  CAS  PubMed  Google Scholar 

  39. C. Najera, J. M. Sansano, Org. Biomol. Chem., 2009, 7, 4567–4581; DOI: https://doi.org/10.1039/b913066g.

    Article  CAS  PubMed  Google Scholar 

  40. X. P. He, Y. L. Zeng, Y. Zang, J. Li, R. A. Field, G. R. Chen, Carbohydr. Res., 2016, 429, 1–22; DOI: https://doi.org/10.1016/j.carres.2016.03.022.

    Article  CAS  PubMed  Google Scholar 

  41. V. K. Tiwari, B. B. Mishra, K. B. Mishra, N. Mishra, A. S. Singh, X. Chen, Chem. Rev., 2016, 116, 3086–3240; DOI: https://doi.org/10.1021/acs.chemrev.5b00408.

    Article  CAS  PubMed  Google Scholar 

  42. V. Poonthiyil, T. K. Lindhorst, V. B. Golovko, A. J. Fairbanks, Beilstein J. Org. Chem., 2018, 14, 11–24; DOI: https://doi.org/10.3762/bjoc.14.2.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  43. A. K. Agrahari, P. Bose, M. K. Jaiswal, S. Rajkhowa, A. S. Singh, S. Hotha, N. Mishra, V. K. Tiwari, Chem. Rev., 2021, 121, 7638–7956; DOI: https://doi.org/10.1021/acs.chemrev.0c00920.

    Article  CAS  PubMed  Google Scholar 

  44. N. Y. Savelyeva, A. M. Shpirt, A. V. Orlova, A. O. Chizhov, L. O. Kononov, Russ. Chem. Bull., 2022, 71, 1784–1793; DOI: https://doi.org/10.1007/s11172-022-3590-3.

    Article  CAS  Google Scholar 

  45. A. S. Kritchenkov, Yu. A. Skorik, Russ. Chem. Bull., 2017, 66, 769–781; DOI: https://doi.org/10.1007/s11172-017-1809-5.

    Article  CAS  Google Scholar 

  46. A. A. Druzina, M. Yu. Stogniy, Russ. Chem. Bull., 2021, 70, 527–532; DOI: https://doi.org/10.1007/s11172-021-3119-1.

    Article  CAS  Google Scholar 

  47. A. Yu. Aksinenko, V. B. Sokolov, A. V. Gabrel’yan, V. V. Grigoriev, S. O. Bachurin, Russ. Chem. Bull., 2021, 70, 2180–2184; DOI: https://doi.org/10.1007/s11172-021-3329-6.

    Article  CAS  Google Scholar 

  48. P. I. Abronina, N. M. Podvalnyy, S. L. Sedinkin, K. G. Fedina, A. I. Zinin, A. O. Chizhov, V. I. Torgov, L. O. Kononov, Synthesis, 2012, 44, 1219–1225; DOI: https://doi.org/10.1055/s-0031-1290752.

    Article  CAS  Google Scholar 

  49. U. Huchel, P. Tiwari, R. R. Schmidt, J. Carbohydr. Chem., 2010, 29, 61–75; DOI: https://doi.org/10.1080/07328301003597673.

    Article  CAS  Google Scholar 

  50. W. L. F. Armarego, Purification of Laboratory Chemicals, 8th ed., Butterworth-Heinemann, 2017, 1198 pp.; DOI: https://doi.org/10.1016/B978-0-12-805457-4.50008-2.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    P. I. Abronina, Yu. S. Shvyrkina, A. I. Zinin, A. O. Chizhov & L. O. Kononov

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  1. P. I. Abronina
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  2. Yu. S. Shvyrkina
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  3. A. I. Zinin
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  4. A. O. Chizhov
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  5. L. O. Kononov
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Correspondence to P. I. Abronina or L. O. Kononov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2740–2750, December, 2022.

This work was financially supported by the Russian Science Foundation (Project No. 21-73-20164).

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Abronina, P.I., Shvyrkina, Y.S., Zinin, A.I. et al. Synthesis of selectively protected α-(1→3)- and α-(1→5)-linked octasaccharide moiety bearing a Janus aglycone, related to the branching site of mycobacterial polysaccharides. Russ Chem Bull 71, 2740–2750 (2022). https://doi.org/10.1007/s11172-022-3703-z

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  • DOI: https://doi.org/10.1007/s11172-022-3703-z

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