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Total chemical synthesis of glycocin F and analogues: S-glycosylation confers improved antimicrobial activity

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Abstract

Glycocin F (GccF) is a unique diglycosylated bacteriocin peptide that possesses potent and reversible bacteriostatic activity against a range of Gram-positive bacteria. GccF is a rare example of a ‘glycoactive’ bacteriocin, with both the O-linked N-acetylglucosamine (GlcNAc) and the unusual S-linked GlcNAc moiety important for antibacterial activity. In this report, glycocin F was successfully prepared using a native chemical ligation strategy and folded into its native structure. The chemically synthesised glycocin appeared to be slightly more active than the recombinant material produced from Lactobacillus plantarum. A second-generation synthetic strategy was used to prepare 2 site selective ‘glyco-mutants’ containing either two S-linked or two O-linked GlcNAc moieties; these mutants were used to probe the contribution of each type of glycosidic linkage to bacteriostatic activity. Replacing the S-linked GlcNAc at residue 43 with an O-linked GlcNAc decreased the antibacterial activity, while replacing O-linked GlcNAc at position 18 with an S-linked GlcNAc increased the bioactivity suggesting that the S-glycosidic linkage may offer a biologically-inspired route towards more active bacteriocins.

Graphical abstract: Total chemical synthesis of glycocin F and analogues: S-glycosylation confers improved antimicrobial activity

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Publication details

The article was received on 10 Oct 2017, accepted on 02 Jan 2018 and first published on 12 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC04383J
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    Total chemical synthesis of glycocin F and analogues: S-glycosylation confers improved antimicrobial activity

    Z. Amso, S. W. Bisset, S. Yang, P. W. R. Harris, T. H. Wright, C. D. Navo, M. L. Patchett, G. E. Norris and M. A. Brimble, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C7SC04383J

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