Skip to main content
SpringerLink
Log in

X-Ray Structure of the Key Synthetic Intermediate of a Cancer-Related Sialyl-Tn Antigen Analogue

  • ORIGINAL PAPER
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

We report herein the synthesis and the X-ray crystal structure of 2-azido-2-deoxy-3,4-O-isopropylidene-α-d-galactopyranosyl-N-oxyphthalimide 3 which is the key-precursor of a cancer-related STn antigen analogue 5. Compound 3 crystallizes from a mixture of dichloromethane/pentane as colorless orthorhombic needles in P2 1 2 1 2 space group with the following cell parameters: a = 14.039(2) Å; b = 16.574(3) Å; c = 8.038(1) Å. The hexapyranose ring of 3 adopts a twisted boat according to the Cremer and Pople puckering parameters (Cremer and Pople, J Am Chem Soc 97:1354, 1975) whereas the structure determination of the corresponding deprotected intermediate 4 (orthorombic colorless prisms, P2 1 2 1 2 1 space group, a = 4.927(3) Å; b = 13.423(2) Å; c = 22.744(3) Å) has revealed a quasi perfect chair.

Index Abstract

We report herein the synthesis and the X-ray crystal structure of 2-azido-2-deoxy-3,4-O-isopropylidene-α-d-galactopyranosyl-N-oxyphthalimide 3 which is the key-precursor of a cancer-related STn antigen analogue 5.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Feizi T, Childs RA (1985) Trends Biochem Sci 10:24

    Article  CAS  Google Scholar 

  2. Hakomori S (1984) Am Rev Immunol 2:103

    Article  CAS  Google Scholar 

  3. Springer GF (1997) J Mol Biol 75:594

    CAS  Google Scholar 

  4. Danishefsky SJ, Allen JR (2000) Angew Chem Int Ed 112:882

    Google Scholar 

  5. Buskas T, Thompson P, Boons G-J (2009) Chem Commun 36:5335

    Article  Google Scholar 

  6. Grigalevicius S, Chierici S, Renaudet O, Lo-Man R, Dériaud E, Leclerc C, Dumy P (2005) Bioconjugate Chem 5:1149

    Article  Google Scholar 

  7. Renaudet O, Křenek K, Bossu I, Dumy P, Kádek A, Adámek D, Vaněk O, Kavan D, Gažák R, Šulc M, Bezouška K, Křen V (2010) J Am Chem Soc 132:6800

    Article  CAS  Google Scholar 

  8. Bettahi I, Dasgupta G, Renaudet O, Chentoufi AA, Zhang X, Carpenter D, Yoon S, Dumy P, BenMohamed L (2009) Cancer Immunol Immunother 58:187

    Article  CAS  Google Scholar 

  9. Renaudet O, BenMohamed L, Dasgupta G, Bettahi I, Dumy P (2008) ChemMedChem 3:737

    Article  CAS  Google Scholar 

  10. Renaudet O, Dasgupta G, Bettahi I, Shi A, Nesburn AB, Dumy P, BenMohamed L (2010) PLoS One 5:e11216

    Article  Google Scholar 

  11. Ragupathi G (1998) Cancer Immunol Immunother 46:82

    Article  Google Scholar 

  12. Renaudet O (2008) Mini-Rev Org Chem 5:274

    Article  CAS  Google Scholar 

  13. Boturyn D, Defrancq E, Dolphin GT, Garcia J, Labbé P, Renaudet O, Dumy P (2008) J Pept Sci 14:224

    Article  CAS  Google Scholar 

  14. Renaudet O, Boturyn D, Dumy P (2009) Bioorg Med Chem Lett 19:3880

    Article  CAS  Google Scholar 

  15. Dendane N, Hoang A, Renaudet O, Vinet F, Dumy P, Defrancq E (2008) Lab Chip 8:2161

    Article  CAS  Google Scholar 

  16. Duléry V, Renaudet O, Wilczewski M, Van der Heyden A, Labbé P, Dumy P (2008) J Comb Chem 10:368

    Article  Google Scholar 

  17. Wilczewski M, Van der Heyden A, Renaudet O, Dumy P, Coche-Guérente L, Labbé P (2008) Org Biomol Chem 6:1114

    Article  CAS  Google Scholar 

  18. Renaudet O, Dumy P (2008) Eur J Org Chem 32:5383

    Article  Google Scholar 

  19. Renaudet O, Dumy P (2006) Org Biomol Chem 4:2628

    Article  CAS  Google Scholar 

  20. Garanger E, Boturyn D, Renaudet O, Defrancq E, Dumy P (2006) J Org Chem 71:2402

    Article  CAS  Google Scholar 

  21. Dubois M-P, Gondran C, Renaudet O, Dumy P, Driguez H, Fort S, Cosnier S (2005) Chem Commun 34:4318

    Article  Google Scholar 

  22. Renaudet O, Dumy P (2005) Bioorg Med Chem Lett 15:3619

    Article  CAS  Google Scholar 

  23. Edupuganti OP, Renaudet O, Defrancq E, Dumy P (2004) Bioorg Med Chem Lett 14:2839

    Article  CAS  Google Scholar 

  24. Renaudet O, Dumy P (2004) Tetrahedron Lett 45:65

    Article  CAS  Google Scholar 

  25. Renaudet O, Reymond J-L (2003) Org Lett 5:4693

    Article  CAS  Google Scholar 

  26. Renaudet O, Dumy P (2002) Tetrahedron 58:2127

    Article  CAS  Google Scholar 

  27. Marcaurelle LA, Shin Y, Goon S, Bertozzi CR (2001) Org Lett 3:3691

    Article  CAS  Google Scholar 

  28. Renaudet O, Dumy P (2001) Tetrahedron Lett 42:7575

    Article  CAS  Google Scholar 

  29. Duléry V, Renaudet O, Philouze C, Dumy P (2007) Carbohydr Res 342:894

    Article  Google Scholar 

  30. Enraf-Nonius CAD-4 Software (1988) Bruker-AXS-Enraf-Nonius, Delft, The Netherlands

  31. Altomare A, Cascarano G, Giacovazzo C, Guagliardi A (1993) J Appl Cryst 26:343

    Article  Google Scholar 

  32. Molecular Structure Corporation TeXsan (1992–1997) Single crystal structure analysis software, version 1.7. MSC, The Woodlands, USA

  33. Johnson CK (1976) ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge

    Google Scholar 

  34. Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor R (1987) J Chem Soc Perkin Trans 2:S1–S2

    Google Scholar 

  35. Cremer D, Pople JA (1975) J Am Chem Soc 97:1354

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Centre National pour la Recherche Scientifique (CNRS), Université Joseph Fourier (UJF) and the COST Action D-34.

Author information

Authors and Affiliations

  1. Département de Chimie Moléculaire, UMR-CNRS 5250 and ICMG FR 2607, Université Joseph Fourier, BP 53, 38041, Grenoble Cedex 9, France

    Olivier Renaudet, Christian Philouze, Corinne Bailly, André Durif & Pascal Dumy

Authors
  1. Olivier Renaudet
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Christian Philouze
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Corinne Bailly
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. André Durif
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Pascal Dumy
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Olivier Renaudet.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Renaudet, O., Philouze, C., Bailly, C. et al. X-Ray Structure of the Key Synthetic Intermediate of a Cancer-Related Sialyl-Tn Antigen Analogue. J Chem Crystallogr 41, 204–208 (2011). https://doi.org/10.1007/s10870-010-9864-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-010-9864-x

Keywords

Search

Navigation