Issue 2, 2012
From the journal:

Organic & Biomolecular Chemistry

Self-association-driven transition of the β-peptidic H12 helix to the H18 helix†‡

Éva Szolnoki,a   Anasztázia Hetényi,b   Tamás A. Martinek,*a   Zsolt Szakonyia  and  Ferenc Fülöpa  

* Corresponding authors

a Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6., H-6720 Szeged, Hungary
E-mail: martinek@pharm.u-szeged.hu
Fax: +36 62545705
Tel: +36 62545564

b Department of Medical Chemistry, University of Szeged, Dóm tér 8., H-6720 Szeged, Hungary

Abstract

Various patterns of foldameric oligomers formed by trans-ABHC ((1S,2S,3S,5S)-2-amino-6,6-dimethylbicyclo[3.3.1]heptane-3-carboxylic acid) and β3-hSer residues were studied. NMR, ECD and molecular modelling demonstrated that octameric and nonameric sequences with multiple i–i+3 ABHC pair repulsions attain the β-H18 helix in CD3OH. As a close relative of the α-helix, this helix type is stabilized by i–i+4 backbone H-bond interactions. The formation of the β-H18 helix was found to be solvent- and concentration-dependent. Upon dilution, the β-H18 → β-H12 helix transition was revealed by concentration-dependent ECD, DOSY-NMR and TEM measurements.

Graphical abstract: Self-association-driven transition of the β-peptidic H12 helix to the H18 helix

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Article information

DOI
https://doi.org/10.1039/C1OB06627G
Article type
Communication
Submitted
23 Sep 2011
Accepted
26 Oct 2011
First published
26 Oct 2011

Org. Biomol. Chem., 2012,10, 255-259

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Self-association-driven transition of the β-peptidic H12 helix to the H18 helix

É. Szolnoki, A. Hetényi, T. A. Martinek, Z. Szakonyi and F. Fülöp, Org. Biomol. Chem., 2012, 10, 255 DOI: 10.1039/C1OB06627G

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