Synthesis of the Antimicrobial S‐Linked Glycopeptide,Glycocin F |
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| Authors: | Prof. Margaret A. Brimble Dr. Pat J. Edwards Dr. Paul W. R. Harris Dr. Gillian E. Norris Dr. Mark L. Patchett Tom H. Wright Dr. Sung‐Hyun Yang Dr. Sarah E. Carley |
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| Affiliation: | 1. School of Chemical Sciences, The University of Auckland, 23 Symonds St., Auckland 1142 (New Zealand);2. Maurice Wilkins Centre for Molecular Biodiscovery, School of Biological Sciences, The University of Auckland, Auckland 1142 (New Zealand);3. Institute of Fundamental Sciences, Massey University, Palmerston North 4442 (New Zealand) |
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| Abstract: | The first total synthesis of glycocin F, a uniquely diglycosylated antimicrobial peptide bearing a rare S‐linked N‐acetylglucosamine (GlcNAc) moiety in addition to an O‐linked GlcNAc, has been accomplished using a native chemical ligation strategy. The synthetic and naturally occurring peptides were compared by HPLC, mass spectrometry, NMR and CD spectroscopy, and their stability towards chymotrypsin digestion and antimicrobial activity were measured. This is the first comprehensive structural and functional comparison of a naturally occurring glycocin with an active synthetic analogue. |
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| Keywords: | antimicrobial peptides disulfide glycocin F glycopeptides glycosylation |
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