Skip to main content
SpringerLink
Log in

Convergent synthesis of the tetrasaccharide repeating unit corresponding to the O-antigen of the verotoxin-producing Escherichia coli O176

  • Published:
Glycoconjugate Journal Aims and scope Submit manuscript

Abstract

A convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of the verotoxin producing E. coli O176 has been achieved in excellent yield adopting a [2 + 2] block glycosylation strategy. The β-D-mannosidic moiety of the tetrasaccharide was prepared from β-D-glucoside and α-D-galactosamine moiety was derived from D-galactal. The tetrasaccharide was synthesized as its 2-trimethylsilylethyl glycoside in excellent yield. All intermediate steps are high yielding.

A convergent synthetic strategy of the tetrasaccharide repeating unit corresponding to the O-antigen of verotoxin-producing Escherichia coli has been successfully developed using stereoselective [2 + 2] block glycosylation technique.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Scheme 1

Similar content being viewed by others

References

  1. Abbott, S.L., O’Conner, J., Robin, T., Zimmer, B.L., Janda, J.M.: Biochemical properties of a newly described Escherichia species, Escherichia albertii. J Clin Microbiol 41, 4852–4854 (2003)

    Article  PubMed  CAS  Google Scholar 

  2. Orskov, I., Orskov, F., Jann, B., Jann, K.: Serology, chemistry, and genetics of O and K antigens of Escherichia coli. Bacterial Rev 41, 667–710 (1977)

    CAS  Google Scholar 

  3. Welinder-Olsson, C., Kaijser, B.: Enterohemorrhagic Escherichia coli (EHEC). Scand J Infect Dis 37, 405–416 (2005)

    Article  PubMed  CAS  Google Scholar 

  4. Karch, H., Tarr, P., Bielaszewska, M.: Enterohaemorrhagic Escherichia coli in human medicine. Int. J. Med. Microbiol. 295, 405–418 (2005)

    Article  PubMed  CAS  Google Scholar 

  5. Ezawa, A., Gocho, F., Saitoh, M., Tamura, T., Kawata, K., Takahashi, T., Kikuchi, N.: A three year study of enterohemorrhagic Escherichia coli O157 on a farm in Japan. J. Vet. Med. Sc. 66, 779–784 (2004)

    Article  Google Scholar 

  6. Boyce, T.G., Swerdlow, D.L., Griffin, P.M.: Escherichia coli O157:H7 and the hemolytic-Uremic Syndrome. N Engl J Med 1995(333), 364–368 (1995)

    Article  Google Scholar 

  7. Stenutz, R., Weintraub, A., Widmalm, G.: The structures of Escherichia coli O-polysaccharide antigens. FEMS Microbiol Rev 30, 382–403 (2006)

    Article  PubMed  CAS  Google Scholar 

  8. Olsson, U., Weintraub, A., Widmalm, G.: Structural determination of the O-antigenic polysaccharide from the verocytotoxin-producing Escherichia coli O176. Carbohydr Res 343, 805–809 (2008)

    Article  PubMed  CAS  Google Scholar 

  9. Roy, R.: New trends in carbohydrate based vaccines. Drug Discov Today Tech 1, 327–336 (2004)

    Article  CAS  Google Scholar 

  10. Doshi, G.M., Shanbhag, P.P., Aggarwal, G.V., Shahare, M.D., Martis, E.A.: Carbohydrate Vaccines- A burgeoning field of Glycomics. J Appl Pharm Sci 1, 17–22 (2011)

    Google Scholar 

  11. Jansson, K., Ahlfors, S., Frejd, T., Kihlberg, J., Magnusson, G.: 2-(Trimethylsilyl)ethyl glycosides. Synthesis, anomeric deblocking and transformation into 1,2-trans 1-O-acyl sugars. J. Org. Chem. 53, 5629–5647 (1988)

    Article  CAS  Google Scholar 

  12. Mukhopadhyay, B., Collet, B., Field, R.A.: Glycosylation reactions with ‘disarmed’ thioglycoside donors promoted by N-iodosuccinimide and HClO4-silica. Tetrahedron Lett 46, 5923–5925 (2005)

    Article  CAS  Google Scholar 

  13. Mukherjee, C., Misra, A. K.: Glycosylation and pyranose-furanose isomerization of carbohydrates using HClO4-SiO2: synthesis of oligosaccharides containing galactofuranose. Synthesis 683–692 (2007)

  14. Chakraborti, A. K., Gulhane, R.: Perchloric acid adsorbed on silica gel as a new, highly efficient and versatile catalyst for acetylation of phenols, thiols, alcohols and amines. Chem. Commun. 1896–1897 (2003)

  15. Kanie, O., Ito, Y., Ogawa, T.: Orthogonal glycosylation strategy in oligosaccharide synthesis. J Am Chem Soc 116, 12073–12074 (1994)

    Article  CAS  Google Scholar 

  16. Misra, A.K., Roy, N.: Synthesis of a mannotetraose derivative related to the antigen from Escherichia coli O9a:K26:H-. Ind J Chem 36B, 308–311 (1997)

    CAS  Google Scholar 

  17. Schmidt, R.R., Grundler, G.: Glycosylimidates. Pt. 6. α-Bonded disaccharides from O-(β-D-glycopyranosyl) trichloroacetimidates with trimethylsilyltrifluoromethane sulfonate as catalyst. Angewandte Chemie 94, 790–791 (1982)

    Article  CAS  Google Scholar 

  18. Sarkar, S.K., Mukhopadhyay, B., Roy, N.: Revised synthesis of pentasaccharide related to the repeating unit of the O-antigen from Shigella dysenteriae type 4 in the form of its methyl ester 2-(trimethylsilyl)ethyl glycoside. Ind J Chem 44B, 1058–1063 (2005)

    CAS  Google Scholar 

  19. Pearlman, W.M.: Noble metal hydroxides on carbon non pyrophoric dry catalysts. Tetrahedron Lett 8, 1663–1664 (1967)

    Article  Google Scholar 

Download references

Acknowledgements

G. G. thanks CSIR, New Delhi for providing a Senior Research fellowship. This project was supported by Bose Institute, Kolkata.

Author information

Authors and Affiliations

  1. Molecular Medicine Division, Bose Institute, P-1/12, C.I.T. Scheme VII M, Kolkata, 700054, India

    Goutam Guchhait & Anup Kumar Misra

Authors
  1. Goutam Guchhait
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anup Kumar Misra
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Anup Kumar Misra.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Guchhait, G., Misra, A.K. Convergent synthesis of the tetrasaccharide repeating unit corresponding to the O-antigen of the verotoxin-producing Escherichia coli O176. Glycoconj J 28, 519–524 (2011). https://doi.org/10.1007/s10719-011-9351-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10719-011-9351-4

Keywords

Search

Navigation