Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of the 2'-Azidoethyl Trisaccharide, 6d-altroHepp-GlcNAc-Gal Hapten, an O-Antigenic Repeating Unit of Campylobacter jejuni Serotypes O:23 and O:36

  • Yun, Mi-Kyung (Department of Applied Chemistry, Dongyang Technical College) ;
  • Shin, Jeong E. Nam (Department of Chemistry, Soongsil University)
  • Published : 2008.07.20
Download PDF
⟨ Previous Next ⟩

Abstract

A trisaccharide, 6d-Altro-Hepp$\alpha$ (1$\rightarrow$3) GlcNAc$\beta$ (1$\rightarrow$3) Gal$\alpha$ (1$\rightarrow$$OCH_2CH_2N_3$, as an O-antigenic repeating unit of Campylobacter jejuni serotypes O:23 and O:36, was synthesized. Coupling of the 6d-altro-Hepp$\alpha$ (1$\rightarrow$3) GlcNAc$\beta$ (1$\rightarrow$SEt donor with Gal$\alpha$ (1${\rightarrow}OCH_2CH_2Cl$ acceptor in the presence of NIS-TfOH promoter afforded the trisaccharide having the $\beta$ (1$\rightarrow$3) Gal linkage. $\beta$ -Stereospecificity and the desired regioselectivity for the 3-OH Gal are obtained. Subsequent hydrogenation, acetylation, azide displacement, hydrazinolysis, Nacetylation, and finally deacetylation furnished the title trisaccharide hapten for further glycoconjugation.

Keywords

References

  1. Salloway, S.; Mermel, L. A.; Seamans, M.; Aspinall, G. O.; Nam Shin, J. E.; Kurjanczyk, L. A.; Penner, J. L. Infect. Immun. 1996, 64, 2945
  2. Nam Shin, J. E.; Ackloo, S.; Mainkar, A. S.; Montriro, M. A.; Pang, H.; Penner, J. L.; Aspinall, G. O. Carbohydr. Res. 1998, 305, 223 https://doi.org/10.1016/S0008-6215(97)00259-0
  3. Aspinall, G. O.; McDonald, A. G.; Raju, T. S.; Pang, H.; Moran, A. P.; Penner, J. L. Eur. J. Biochem. 1993, 213, 1017 https://doi.org/10.1111/j.1432-1033.1993.tb17849.x
  4. Aspinall, G. O.; McDonald, A. G.; Raju, T. S.; Pang, H.; Kurjanczyk, L. A.; Penner, J. L.; Maran, A. P. Eur. J. Biochem. 1993, 231, 1029
  5. Aspinall, G. O.; McDonald, A. G.; Raju, T. S.; Pang, H.; Mills, S. D.; Kurjanczyk, L. A.; Penner, J. L. J. Bacteriol. 1992, 174, 1324 https://doi.org/10.1128/jb.174.4.1324-1332.1992
  6. Aspinall, G. O.; McDonald, A. G.; Pang, H. Carbohydr. Res. 1992, 231, 13 https://doi.org/10.1016/0008-6215(92)84003-B
  7. Aspinall, G. O.; Fujimoto, S.; McDonald, A. G.; Pang, H.; Kurjanczyk, L. A.; Penner, J. L. Infect. Immun. 1994, 62, 2122
  8. Yun, M.; Nam Shin, J. E. J. Graduate School Soongsil Univ., 1999
  9. Yun, M.; Yoon, S.; Chun, K. H.; Nam Shin, J. E. Agricultural Biotechnology Sym. 1995, 51
  10. Yun, M.; Yoon, S.; Shin, Y.; Chun, K. H.; Nam Shin, J. E. Arch. Pharm. Res. 2004, 27, 143 https://doi.org/10.1007/BF02980097
  11. Yoon, S.; Shin, Y.; Chun, K. H.; Nam Shin, J. E. Bull. Korean Chem. Soc. 2004, 25, 289 https://doi.org/10.5012/bkcs.2004.25.2.289
  12. Mancuso, A. J.; Swern, D. Synthesis 1981, 165
  13. Veeneman, G. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 275 https://doi.org/10.1016/S0040-4039(00)94391-0
  14. Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331 https://doi.org/10.1016/S0040-4039(00)88799-7
  15. Yun, M.; Shin, Y.; Chun, K. H.; Nam Shin, J. E. Bull. Korean Chem. Soc. 2000, 21, 562 https://doi.org/10.1007/BF02705488
  16. Yun, M. PhD. Thesis 1999, Part III, 63
  17. Yun, M.; Shin, Y.; Yoon, S.; Chun, K. H.; Nam Shin, J. E. Bull. Korean Chem. Soc. 1998, 19, 1239
  18. Leung, O-T.; Douglas, S. P.; Whitfield, D. M.; Pang, H. Y. S.; Krepinsky, J. J. New. J. Chem. 1994, 18, 349
  19. Whitfield, D. M.; Pang, H.; Carver, J. P.; Krepinsky, J. J. Can. J. Chem. 1990, 68, 942 https://doi.org/10.1139/v90-147
  20. Verduyn, R.; van der Klein, P. A. M.; Douwes, M.; van der Marel, G. A.; van Boom, J. H. Recl. Trav. Chim. Pays-Bas 1993, 112, 464 https://doi.org/10.1002/recl.19931120707

Cited by

  1. -Methyl Phosphoramidate Motif pp.00448249, 2018, https://doi.org/10.1002/ange.201810222
  2. -Methyl Phosphoramidate Motif pp.14337851, 2018, https://doi.org/10.1002/anie.201810222
  3. Progress toward the Development of Glycan-Based Vaccines against Campylobacteriosis vol.7, pp.5, 2008, https://doi.org/10.1021/acsinfecdis.0c00332