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Hydrate of 2,3:4,5-di-O-isopropylidene-β-D-arabino-hexos-2-ulo-2,6-pyranose as new crystalline reagent in the preparation of Amadori derived peptides

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Central European Journal of Chemistry

Abstract

We established, that crystalline hydrate of 2,3:4,5-di-O-isopropylidene-β-D-arabino-hexos-2-ulo-2,6-pyranose is a new, convenient and stable reagent for solid phase synthesis of peptide derived Amadori products. The structure of the title compound was studied by X-ray analysis, NMR spectroscopy, and high resolution ESI-MS. The crystal structure indicated the existence of two symmetry-independent molecules that were not connected with hydrogen bonds. A comparison with previously reported 2,3:4,5-di-O-isopropylidene-β-D-fructopyranose revealed, that these two compounds are isostructural.

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References

  1. R. Singh, A. Barden, T. Mori, L. Beilin, Diabetologia 44, 129 (2001)

    Article  CAS  Google Scholar 

  2. S, Kikuchi, K. Shinpo, M. Takeuchi, S. Yamagishi, Z. Makita, K. Tashiro, Brain Res. Rev. 41, 306 (2003)

    Article  CAS  Google Scholar 

  3. A.M. McKillop, Y.H. Abdel-Wahab, M.H. Mooney, F.P.M. O’Harte, P.R. Flatt, Diabet. Metab. 28, 61 (2002)

    Google Scholar 

  4. A.M. McKillop, A. Meade, P.R. Flatt, F.P.M. O’Harte, Regul. Peptides 113, 1 (2003)

    Article  CAS  Google Scholar 

  5. P. Stefanowicz, K. Kapczyńska, A. Kluczyk, Z. Szewczuk, Tetrahedron Lett. 48, 967 (2007)

    Article  CAS  Google Scholar 

  6. A. Frolov, D. Singer, R. Hoffmann, J. Pept. Sci. 13, 862 (2007)

    Article  CAS  Google Scholar 

  7. P. Stefanowicz, M. Kijewska, K. Kapczyńska, Z. Szewczuk, Amino Acids, in press, DOI 10.1007/s00726-009-0294-z

  8. S. Carganico, P. Rovero, J.A. Halperin, A.M. Papini, M. Chorev, J. Pept. Sci. 15, 67 (2009)

    Article  CAS  Google Scholar 

  9. N.J. Forrow, M.J. Batchelor, Tetrahedron Lett. 31, 3493 (1990)

    Article  CAS  Google Scholar 

  10. S. Horvat, A. Jakas, J. Pept. Sci. 10, 119 (2004)

    Article  CAS  Google Scholar 

  11. I.I. Cubero, M.T.P. Lopez-Espinosa, Carbohydr. Res. 205, 293 (1990)

    Article  Google Scholar 

  12. K.H. Aamlid, L. Hough, A.C. Richardson, Carbohydr. Res. 202, 117 (1990)

    Article  CAS  Google Scholar 

  13. R.W. Lowe, W.A. Szarek, J.K.N. Jones, Carbohydr. Res. 28, 281 (1973)

    Article  CAS  Google Scholar 

  14. R.F. Brady Jr, Carbohydr. Res. 15, 35 (1970)

    Article  CAS  Google Scholar 

  15. Bruker, SHELXTL. Version 5.10. (Bruker AXS Inc., Madison, WI, 1997)

    Google Scholar 

  16. P. Roepstorff, J. Fohlmann, Biomed. Mass Spectrom. 11, 601 (1984)

    Article  CAS  Google Scholar 

  17. T. Lis, A. Weichsel, Acta Cryst. C43, 1954 (1987)

    CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Faculty of Chemistry, University of Wrocław, 50-383, Wrocław, Poland

    Piotr Stefanowicz, Joanna Batorska, Monika Kijewska, Hubert Bartosz-Bechowski, Zbigniew Szewczuk & Tadeusz Lis

Authors
  1. Piotr Stefanowicz
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  2. Joanna Batorska
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  3. Monika Kijewska
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  4. Hubert Bartosz-Bechowski
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  5. Zbigniew Szewczuk
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  6. Tadeusz Lis
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Correspondence to Piotr Stefanowicz.

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Stefanowicz, P., Batorska, J., Kijewska, M. et al. Hydrate of 2,3:4,5-di-O-isopropylidene-β-D-arabino-hexos-2-ulo-2,6-pyranose as new crystalline reagent in the preparation of Amadori derived peptides. cent.eur.j.chem. 8, 28–33 (2010). https://doi.org/10.2478/s11532-009-0123-y

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  • DOI: https://doi.org/10.2478/s11532-009-0123-y

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