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Synlett 2009(8): 1233-1236  
DOI: 10.1055/s-0028-1088128
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Use of ‘Click Chemistry’ for the Synthesis of Tetrazole-Containing Analogues of the Neuroprotective Agent Glycyl-l-prolyl-l-glutamic Acid

Kuo-yuan Hung, Paul W. R. Harris, Margaret A. Brimble*
Department of Chemistry, University of Auckland, 23 Symonds Street, Auckland 1142, New Zealand
Fax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz ;
Further Information

Publication History

Received 11 February 2009
Publication Date:
08 April 2009 (online)

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Abstract

Tetrazole-containing analogues of glycyl-l-prolyl-l-glutamic acid (GPE) were prepared by coupling of Cbz-glycyl-l-proline with tetrazole-containing glutamic acids followed by hydrogenation of the resultant tripeptide. Synthesis of the tetrazole-­containing glutamic acids involved 1,3-dipolar cycloaddition of ­sodium azide to nitrile derivatives of the corresponding glutamic ­acids.

Key words

GPE - 1,3-dipolar cycloaddition - tetrazole - TMSI - BoPCl

    References

  • 1 Yamamoto H. Murphy L. Endocrinology  1994,  2432 
    CrossrefGoogle Scholar
  • 2 Guan J. Waldvogel H. Faull R. Gluckman P. Williams C. Neuroscience  1999,  649 
    CrossrefGoogle Scholar
  • 3a Trotter N. Brimble M. Harris P. Callis D. Sieg F. Bioorg. Med. Chem.  2005,  501 
    Google Scholar
  • 3b Brimble M. Trotter N. Harris P. Sieg F. Bioorg. Med. Chem.  2005,  519 
    Google Scholar
  • 3c Lai M. Brimble M. Callis D. Harris P. Levi M. Sieg F. Bioorg. Med. Chem.  2005,  533 
    Google Scholar
  • 3d Harris P. Brimble M. Muir V. Lai M. Trotter N. Callis D. Tetrahedron  2005,  10018 
    Google Scholar
  • 3e De Diego S. Muñoz P. González-Muñiz R. Herranz R. Martín-Martínez M. Cenarruzabeitia E. Frechilla D. Del Río J. Jimeno M. García-López M. Bioorg. Med. Chem. Lett.  2005,  2279 
    Google Scholar
  • 4 Thornber C. Chem. Soc. Rev.  1979,  563 
    CrossrefGoogle Scholar
  • 5a Duncia J. Carini D. Chui A. Johnson A. Price W. Wong P. Wexler R. Timmermans P. Med. Res. Rev.  1992,  149 
    Google Scholar
  • 5b Chu S. Drugs Future  1985,  632 
    Google Scholar
  • 6 Detsi A. Micha-Screttas M. Igglessi-Markopoulou O. J. Chem. Soc., Perkin Trans. 1  1998,  2243 
    CrossrefGoogle Scholar
  • 7 Adams E. Int. J. Pept. Protein Res.  1976,  503 
    Google Scholar
  • 8 Demko Z. Sharpless K. Org. Lett.  2002,  2525 
    CrossrefGoogle Scholar
  • 9 Sureshbabu V. Venkataramanarao R. Naik S. Chennakrishmareddy G. Tetrahedron Lett.  2007,  7038 
    CrossrefGoogle Scholar
  • 10 Tong A. Harris P. Barker D. Brimble M. Eur. J. Org. Chem.  2008,  164 
    CrossrefGoogle Scholar
  • 11 Lott R. Chauhan V. Stammer C. J. Chem. Soc., Chem. Commun.  1979,  495 
    CrossrefGoogle Scholar