Chiral Sulfoxide-Induced Single Turn Peptide α-Helicity.
Sci Rep
; 6: 38573, 2016 12 09.
Article
en En
| MEDLINE
| ID: mdl-27934919
ABSTRACT
Inducing α-helicity through side-chain cross-linking is a strategy that has been pursued to improve peptide conformational rigidity and bio-availability. Here we describe the preparation of small peptides tethered to chiral sulfoxide-containing macrocyclic rings. Furthermore, a study of structure-activity relationships (SARs) disclosed properties with respect to ring size, sulfur position, oxidation state, and stereochemistry that show a propensity to induce α-helicity. Supporting data include circular dichroism spectroscopy (CD), NMR spectroscopy, and a single crystal X-ray structure for one such stabilized peptide. Finally, theoretical studies are presented to elucidate the effect of chiral sulfoxides in inducing backbone α-helicity.
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Péptidos
/
Safrol
/
Conformación Proteica en Hélice alfa
Idioma:
En
Año:
2016
Tipo del documento:
Article