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NXO beta structure mimicry: an ultrashort turn/hairpin mimic that folds in water
Vienna University of Technology, Austria .
University of Vienna, Austria .
Slovak University of Technology Bratislava, Slovakia .
Slovak University of Technology Bratislava, Slovakia .
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2014 (English)In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 4, no 41, 21351-21360 p.Article in journal (Refereed) Published
Abstract [en]

We report the first application of NXO-pseudopeptides for beta-turn mimicry. Incorporating the proline-derived NProO peptidomimetic building block, a minimal tetrapeptide beta-hairpin mimic has been designed, synthesized and its solution structure elucidated. Emulating a natural proline-glycine beta-turn, evidence from NMR, molecular modeling and CD suggests the formation of two rapidly interconverting hairpin folds in water, methanol and dimethyl-sulfoxide at room temperature, displaying the proline nitrogen amide bond in either cis or trans arrangement. The NProO-modified hairpin features peptidic backbone dihedrals phi, Psi characteristic of natural proline-containing turns composed of alpha-amino acids only. Taken together, the observed folding behavior and inherently high designability render the NProO motif a building block for beta-structure elaboration in aqueous medium.

Place, publisher, year, edition, pages
Royal Society of Chemistry , 2014. Vol. 4, no 41, 21351-21360 p.
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Engineering and Technology
Identifiers
URN: urn:nbn:se:liu:diva-108819DOI: 10.1039/c4ra01210kISI: 000336837100026OAI: oai:DiVA.org:liu-108819DiVA: diva2:732878
Available from: 2014-07-07 Created: 2014-07-06 Last updated: 2017-12-05

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