Poster Presentation 11th Australian Peptide Conference 2015

Solid-Phase Synthesis of Azotides and Their Employment in Green Catalysis (#131)

Christian Borch Jacobsen 1 , Frederik Diness 1 , Morten Meldal 1
  1. Department of Chemistry, University of Copenhagen, Copenhagen, Denmark

Azotides, peptides that contain at least one azole or azoline moiety, are widespread in nature. Whereas the biological activities of a few of these peptides have been elucidated, the avenues regarding their potential utilization in catalytic systems are largely unexplored.

The key structural features of azotides are the azole and azoline moieties; moieties that are well-known for coordinating a range of transition metals. Combining these features with the advantages of peptide-based ligands, we aim to develop a range of novel linear and cyclic complexes that can revolutionize the use of such ligands in catalytic systems.

This presentation will focus on the synthesis of azole and azoline building blocks from amino acid precursors, their employment in solid-phase synthesis into azotides as well as the azotides´s utilization in catalytic reactions.

  1. For selected examples of naturally occurring azotides see: a) C. Zhang et al., J. Am. Chem. Soc., 2008, 130, 12102. b) C. J. Hawkins, M. F. Lavin, K. A. Marshall, A. L. Brenk, D. J. Watters, J. Med. Chem., 1990, 33, 1634. c) H. Luesch, W. Y. Yoshida, R. E. Moore, V. J. Paul, J. Nat. Prod., 2000, 63, 1106. d) D. S. Dalisay, E. W. Rogers, A. S. Edison, T. F. Molinski, J. Nat. Prod., 2009, 72, 732.
  2. For a review on azole and azoline metal coordination see: a) G. Desimoni, G. Faita, K. A. Jørgensen, Chem. Rev., 2006, 106, 3561.