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A Chemical Biology Approach to Understanding Molecular Recognition of Lipid II by Nisin(1-12): Synthesis and NMR Ensemble Analysis of Nisin(1-12) and Analogues
UCL, Dept Chem, 20 Gordon St, London WC1H 0AJ, England.ORCID iD: 0000-0003-3139-5423
Swedish NMR Ctr, Medicinaregatan 5, S-40530 Gothenburg, Sweden.
UCL, Dept Chem, 20 Gordon St, London WC1H 0AJ, England.
UCL, Div Biosci, Inst Struct & Mol Biol, Gower St, London WC1E 6BT, England.
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2019 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 25, no 64, p. 14572-14582Article in journal (Refereed) Published
Abstract [en]

Natural products that target lipid II, such as the lantibiotic nisin, are strategically important in the development of new antibacterial agents to combat the rise of antimicrobial resistance. Understanding the structural factors that govern the highly selective molecular recognition of lipid II by the N-terminal region of nisin, nisin(1-12), is a crucial step in exploiting the potential of such compounds. In order to elucidate the relationships between amino acid sequence and conformation of this bicyclic peptide fragment, we have used solid-phase peptide synthesis to prepare two novel analogues of nisin(1-12) in which the dehydro residues have been replaced. We have carried out an NMR ensemble analysis of one of these analogues and of the wild-type nisin(1-12) peptide in order to compare the conformations of these two bicyclic peptides. Our analysis has shown the effects of residue mutation on ring conformation. We have also demonstrated that the individual rings of nisin(1-12) are pre-organised to an extent for binding to the pyrophosphate group of lipid II, with a high degree of flexibility exhibited in the central amide bond joining the two rings.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2019. Vol. 25, no 64, p. 14572-14582
Keywords [en]
antibiotics, cyclic peptides, lantibiotics, NMR spectroscopy, solid phase synthesis
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-399097DOI: 10.1002/chem.201902814ISI: 000489322000001PubMedID: 31599485OAI: oai:DiVA.org:uu-399097DiVA, id: diva2:1378581
Funder
Swedish Research Council, 2016:03602Wellcome trust, 101569/z/13/zAvailable from: 2019-12-13 Created: 2019-12-13 Last updated: 2019-12-13Bibliographically approved

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