Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH FRONT

Synthesis of MUC1 Peptide and Glycopeptide Dendrimers

Candy K. Y. Chun A and Richard J. Payne A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry, The University of Sydney, NSW 2006, Australia.

B Corresponding author. Email: payne@chem.usyd.edu.au

Australian Journal of Chemistry 62(10) 1339-1343 https://doi.org/10.1071/CH09282
Submitted: 12 May 2009  Accepted: 19 June 2009   Published: 13 October 2009

Abstract

Several dendrimers possessing multiple copies of peptides and glycopeptides belonging to the MUC1 eicosapeptide tandem repeat sequence have been prepared. Fmoc-strategy solid-phase peptide synthesis was used to construct the peptides and glycopeptides, which were conjugated to suitably functionalized dendrimer cores using the copper-catalyzed azide-alkyne cycloaddition reaction to produce multivalent peptide and glycopeptide dendrimers.


Acknowledgements

We would like to thank the Australian Research Council for funding and Yves Hsieh for assistance with MALDI-TOF mass spectrometry.


References


[1]   A. Varki, Glycobiology 1993, 3,  97.
        | CrossRef |  CAS |  open url image1

[2]   R. G. Spiro, Glycobiology 2002, 12,  43R.
        | CrossRef |  CAS |  open url image1

[3]   R. A. Dwek, Chem. Rev. 1996, 96,  683.
        | CrossRef |  CAS |  open url image1

[4]   F.-G. Hanisch, S. Muller, Glycobiology 2000, 10,  439.
        | CrossRef |  CAS |  open url image1

[5]   H. Kunz, J. Pept. Sci. 2003, 9,  563.
        | CrossRef |  CAS |  open url image1

[6]   H. Herzner, T. Reipen, M. Schultz, H. Kunz, Chem. Rev. 2000, 100,  4495.
        | CrossRef |  CAS |  open url image1

[7]   T. Buskas, S. Ingale, G. J. Boons, Glycobiology 2006, 16,  113R.
        | CrossRef |  CAS |  open url image1

[8]   S. J. Danishefsky, J. R. Allen, Angew. Chem. Int. Ed. 2000, 39,  836.
        | CrossRef |  CAS |  open url image1

[9]   S. Dziadek, H. Kunz, Chem. Rec. 2004, 3,  308.
        | CrossRef |  CAS |  open url image1

[10]   O. Ouerfelli, J. D. Warren, R. M. Wilson, S. J. Danishefsky, Expert Rev. Vaccines 2005, 4,  677.
        | CrossRef |  CAS |  open url image1

[11]   C. Brocke, H. Kunz, Bioorg. Med. Chem. 2002, 10,  3085.
        | CrossRef |  CAS |  open url image1

[12]   M. Meldal, P. M. St Hilaire, Curr. Opin. Chem. Biol. 1997, 1,  552.
        | CrossRef |  CAS |  open url image1

[13]   S. Dziadek, C. G. Espinola, H. Kunz, Aust. J. Chem. 2003, 56,  519.
        | CrossRef |  CAS |  open url image1

[14]   G. F. Springer, Science 1984, 224,  1198.
        | CrossRef |  CAS |  open url image1

[15]   S. Dziadek, C. Griesinger, H. Kunz, U. M. Reinscheid, Chem. Eur. J. 2006, 12,  4981.
        | CrossRef |  CAS |  open url image1

[16]   A. L. Sorensen, C. A. Reis, M. A. Tarp, U. Mandel, K. Ramachandran, V. Sankaranarayanan, T. Schwientek, R. Graham, J. Taylor-Papadimitriou, M. A. Hollingsworth, J. Burchell, H. Clausen, Glycobiology 2006, 16,  96.
        | CrossRef |  CAS |  open url image1

[17]   A. Liakatos, H. Kunz, Curr. Opin. Mol. Ther. 2007, 9,  35.
        |  CAS |  open url image1

[18]   P. Niederhafner, M. Reinis, J. Sebestik, J. Jezek, J. Pept. Sci. 2008, 14,  556.
        | CrossRef |  CAS |  open url image1

[19]   C. Ozawa, H. Katayama, H. Hojo, Y. Nakahara, Org. Lett. 2008, 10,  3531.
        | CrossRef |  CAS |  open url image1

[20]   C. Ozawa, H. Hojo, Y. Nakahara, H. Katayama, K. Nabeshima, T. Akahane, Tetrahedron 2007, 63,  9685.
        | CrossRef |  CAS |  open url image1

[21]   R. Huisgen, G. Szeimies, L. Mobius, Chem. Ber. 1967, 100,  2494.
        | CrossRef |  CAS |  open url image1

[22]   C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67,  3057.
        | CrossRef |   open url image1

[23]   V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41,  2596.
        | CrossRef |  CAS |  open url image1

[24]   E. D. Goddard-Borger, R. V. Stick, Org. Lett. 2007, 9,  3797.
        | CrossRef |  CAS |  open url image1



Rent Article (via Deepdyve) Supplementary MaterialSupplementary Material (581 KB) Export Citation Cited By (11)