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- Title
Plant Antimicrobial Peptides Snakin-1 and Snakin-2: Chemical Synthesis and Insights into the Disulfide Connectivity.
- Authors
Harris, Paul W. R.; Yang, Sung ‐ Hyun; Molina, Antonio; López, Gemma; Middleditch, Martin; Brimble, Margaret A.
- Abstract
Antimicrobial peptides and proteins represent an important class of plant defensive compounds against pathogens and provide a rich source of lead compounds in the field of drug discovery. We describe the effective preparation of the cysteine-rich snakin-1 and -2 antimicrobial peptides by using a combination of solid-phase synthesis and native chemical ligation. A subsequent cysteine/cystine mediated oxidative folding to form the six internal disulfide bonds concurrently gave the folded proteins in 40-50 % yield. By comparative evaluation of mass spectrometry, HPLC, biological data and trypsin digest mapping of folded synthetic snakin-2 compared to natural snakin-2, we demonstrated that synthetic snakin-2 possesses full antifungal activity and displayed similar chromatographic behaviour to natural snakin-2. Trypsin digest analysis allowed tentative assignment of three of the purported six disulfide bonds.
- Subjects
ANTIMICROBIAL peptides; CHEMICAL synthesis; DISULFIDES; PLANT defenses; CYSTEINE
- Publication
Chemistry - A European Journal, 2014, Vol 20, Issue 17, p5102
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201303207