Poster Presentation RACI Biomolecular Division Conference 2013

Total Synthesis of Polydiscamide B-D and Microspinosamide (#86)

Gajan Santhakumar 1 , Richard J Payne 1
  1. University of Sydney, Camperdown, NSW, Australia

With the current decline in new drug approvals, untapped biological resources such as natural products may provide an opportunity for the discovery of new pharmaceutical agents1 . This poster describes a novel approach towards the total synthesis of four structurally related peptide-based natural products 1-4. Polydiscamide B-D2 (1-3) possess agonist activity (EC50 = 1.26, 3.57 and 2.80 mM, respectively) against the human sensory neuron-specific G-protein coupled receptor (SNSR) while Microspinosamide3 (4) possesses potent anti-HIV activity (EC50 = 100 nM).  Assembly of these natural products via an unprecedented native chemical ligation (NCL)-oxidation approach will be described.

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  1. J. W. H. Li, J. C. Vederas, Science 2009, 325, 161-165.
  2. Y. Feng, A. R. Carroll, D. M. Pass, J. K. Archbold, V. M. Avery, R. J. Quinn, J. Nat. Pro., 2007, 71, 8-11.
  3. M. A. Rashid, K. R. Gustafson, L. K. Cartner, N. Shigematsu, L. K. Pannell, M. R. Boyd, J. Nat. Pro., 2000, 64, 117-121.