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Halogen Bonding: An Alternative Tool to Modulate Peptide Conformation
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.ORCID iD: 0000-0003-0359-5970
2017 (English)Conference paper, Oral presentation with published abstract (Refereed)
Abstract [en]

Halogen bonding: an alternative tool to modulate peptide conformation

Emma Danelius(1), Hanna Andersson(1), Patrik Jarvoll(1), Kajsa Lood(1), Jürgen Gräfenstein(1) and  Mate Erdelyi(1,2)

1) Department of Chemistry and Molecular Biology, University of Gothenburg, Sweden

2) Department of Chemistry – BMC, Uppsala University, Sweden   

Halogen bonding is a weak chemical force that resembles hydrogen bonding in many aspects. Despite its potential for use in drug discovery, as a new molecular tool in the direction of molecular recognition events, it has so far rarely been assessed in biopolymers. Motivated by this fact, we have developed a peptide model system that permits the quantitative evaluation of weak forces in a biologically relevant proteinlike environment and have applied it for the assessment of a halogen bond formed between two amino acid side chains. 

The influence of a single weak force is measured by detection of the extent to which it modulates the conformation of a cooperatively folding system. We have optimized the amino acid sequence of the model peptide on analogues with a hydrogen bond-forming site as a model for the intramolecular halogen bond to be studied, demonstrating the ability of the technique to provide information about any type of weak secondary interaction. 

A combined solution nuclear magnetic resonance spectroscopic and computational investigation demonstrates that an interstrand halogen bond is capable of conformational stabilization of a β-hairpin foldamer comparable to an analogous hydrogen bond. This is the first report of incorporation of a conformation-stabilizing halogen bond into a peptide/protein system, and the first quantification of a chlorine-centered halogen bond in a biologically relevant system in solution.  

Place, publisher, year, edition, pages
2017.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-372065OAI: oai:DiVA.org:uu-372065DiVA, id: diva2:1275293
Conference
HBOND 2017, Jyväskylä, Finland, September 11-14.
Available from: 2019-01-04 Created: 2019-01-04 Last updated: 2019-01-07

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