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Halogen bond promoted peptide folding
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry. (Erdelyi group)
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry. (Ederlyi group)ORCID iD: 0000-0003-3798-3322
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2018 (English)Conference paper, Oral presentation with published abstract (Refereed)
Abstract [en]

We have developed a β-hairpin peptide model system that permits quantitative evaluation of weak interactions in a biologically relevant environment. The influence of a single weak force was measured by detection of the extent to which it modulates peptide folding. Initially we have optimized a β-hairpin model system, using the simpler to synthesize hydrogen bonding analogues of our target system encompassing halogen bond donor and acceptor sites [1,2,3]. Using a combined computational and NMR spectroscopic ensemble analysis, we have quantified the stabilizing effect of a single secondary interaction on the folded β-hairpin conformation. We have demonstrated that a chlorine centered halogen bond, formed between two amino acid side chains in an interstrand manner (Figure 1), provides a conformational stabilization comparable to the analogous hydrogen bond [4]. The negative control, i.e. the peptide containing a noninteracting aliphatic side chain, was ~30% less folded than the hydrogen and halogen bonding analogues, revealing the high impact of the interstrand interaction on folding. The experimental results are corroborated by computation on the DFT level. This is the first report of quantification of a conformation-stabilizing chlorine centered halogen bond in a peptide system.  

Place, publisher, year, edition, pages
2018.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-371811OAI: oai:DiVA.org:uu-371811DiVA, id: diva2:1274766
Conference
The 3rd International Symposium on Halogen Bonding, Greenville, USA, June 11-14 2018.
Available from: 2019-01-02 Created: 2019-01-02 Last updated: 2019-01-07

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Danelius, EmmaAndersson, HannaErdélyi, Máté

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