Poster Presentation 7th Modern Solid Phase Peptide Synthesis & Its Applications Symposium 2019

Synthesis and characterisation of an insulin-like peptide from a sea anemone (#140)

Feng Lin 1 , Michela L Mitchell 2 , Dorothy CC Wai 2 , Raymond S Norton 2 , Mohammed Akhter Hossain 1 , John D Wade 1 3
  1. Florey Neuroscience Institute, University of Melbourne, Melbourne, VIC 3010, Australia
  2. Monash Institute of Pharmaceutical Sciences, 381 Royal Parade, Parkville, VIC 3052, Australia
  3. School of Chemistry, University of Melbourne, Melbourne, VIC, Australia

Multiple 'omic' technologies have shown that sea anemones from a range of species produce a wide variety of peptides and proteins, including many ion channel blockers and modulators.1-3 Our transcriptomic analysis of the Australian sea anemone Oulactis sp has revealed the presence of novel, insulin-like sequences (INSLs) in this animal. In order to study their possible biological functions and structure-function relationships, we used our highly optimized Fmoc-SPPS methods4 to prepare each of the A- and B-chains of one putative INSL followed by stepwise regioselective formation of each of the three disulfide bonds - one intra-chain and two inter-chain - in good overall yield. We describe the chemical synthesis together with a preliminary NMR spectroscopic analysis of the peptide.

  1. Prentis, P. J., Pavasovic, A. & Norton, R. S. Toxins 10, 36; doi:10.3390/toxins10010036 (2018)
  2. Mitchell, M. L., Hamilton, B. R., Madio, B. et al. Aust. J. Chem. 70, 1235 (2017)
  3. Shafee, T., Mitchell, M. L. & Norton, R. S. Toxicon 165, 95 (2019)
  4. Hossain, M. A. & Wade, J. D. Accounts Chem Res, 50, 2116 (2017).