NXO beta structure mimicry: an ultrashort turn/hairpin mimic that folds in water
- Author(s)
- Constantin Rabong, Christoph Schuster, Tibor Liptaj, Nadezda Prónayová, Vassil B. Delchev, Ulrich Jordis, Jaywant Phopase
- Abstract
We report the first application of NXO-pseudopeptides for β-turn mimicry. Incorporating the proline-derived NProO peptidomimetic building block, a minimal tetrapeptide β-hairpin mimic has been designed, synthesized and its solution structure elucidated. Emulating a natural proline-glycine β-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 Φ, Ψ characteristic of natural proline-containing turns composed of α-amino acids only. Taken together, the observed folding behavior and inherently high designability render the NProO motif a building block for β-structure elaboration in aqueous medium. This journal is
- Organisation(s)
- External organisation(s)
- Technische Universität Wien, Slovak University of Technology in Bratislava, Paisii Hilendarski University of Plovdiv, Linköping University
- Journal
- RSC Advances
- Volume
- 4
- Pages
- 21351-21360
- No. of pages
- 10
- ISSN
- 2046-2069
- DOI
- https://doi.org/10.1039/C4RA01210K
- Publication date
- 2014
- Austrian Fields of Science 2012
- 104023 Environmental chemistry
- ASJC Scopus subject areas
- General Chemical Engineering, General Chemistry
- Portal url
- https://ucrisportal.univie.ac.at/en/publications/a983f756-0bb6-41ef-acb4-fd0dd728cd5c