Oral Presentation 10th Australian Peptide Conference 2013

Total Chemical Synthesis of the antimicrobial peptides Snakin 1 and 2 (#43)

Paul WR Harris 1 , Margaret A Brimble 1 , Sung-hyun Yang 2 , Antonio Molina 3
  1. School of Chemical Sciences and Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, Auckland 1142, New Zealand
  2. School of Biological Sciences, The University of Auckland, Auckland 1142, New Zealand
  3. Centro de Biotecnología y Genómica de Plantas (CBGP, UPM-INIA), Universidad Politécnica de Madrid (UPM), Campus Montegancedo, M-40 (Km 38), Madrid, Spain

Snakin 11 (63 residues) and Snakin 22 (66 residues) are disulphide rich antimicrobial proteins isolated from solanum tuberosum (potato) tubers. Both are active (1-20 uM) against several fungal and bacterial plant pathogens but due to a lack of readily available material a detailed investigation of their structure and structural requirements for their biological activity remains undetermined. We outline the first synthesis of these intriguing peptides using native chemical ligation techniques and describe the oxidative folding of the 12 cysteines present in the linear polypeptide to afford the postulated 6 disulphide bonds. Both synthetic Snakin 1 and 2 demonstrated full biological activity when compared to natural Snakin 1 peptide. Furthermore, comparison by spectroscopic methods of the folded synthetic Snakin 2 to that obtained from natural sources suggested that these were otherwise identical.

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  2. M. Berrocal-Lobo, A. Segura, M. Moreno, G. López, F. García-Olmedo and A. Molina, Plant Physiol., 2002, 128, 951-961.