de Araujo, Aline D.;
Hoang, Huy N.;
Kok, W. Mei;
Diness, Frederik;
Gupta, Praveer;
Hill, Timothy A.;
Driver, Russell W.;
Price, David A.;
Liras, Spiros;
Fairlie, David P.
Comparative α‐Helicity of Cyclic Pentapeptides in Water
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Medientyp:
E-Artikel
Titel:
Comparative α‐Helicity of Cyclic Pentapeptides in Water
Beteiligte:
de Araujo, Aline D.;
Hoang, Huy N.;
Kok, W. Mei;
Diness, Frederik;
Gupta, Praveer;
Hill, Timothy A.;
Driver, Russell W.;
Price, David A.;
Liras, Spiros;
Fairlie, David P.
Erschienen:
Wiley, 2014
Erschienen in:Angewandte Chemie International Edition
Beschreibung:
<jats:title>Abstract</jats:title><jats:p>Helix‐constrained polypeptides have attracted great interest for modulating protein–protein interactions (PPI). It is not known which are the most effective helix‐inducing strategies for designing PPI agonists/antagonists. Cyclization linkers (X<jats:sub>1</jats:sub>–X<jats:sub>5</jats:sub>) were compared here, using circular dichroism and 2D NMR spectroscopy, for α‐helix induction in simple model pentapeptides, Ac‐cyclo(1,5)‐[X<jats:sub>1</jats:sub>‐Ala‐Ala‐Ala‐X<jats:sub>5</jats:sub>]‐NH<jats:sub>2</jats:sub>, in water. In this very stringent test of helix induction, a Lys1→Asp5 lactam linker conferred greatest α‐helicity, hydrocarbon and triazole linkers induced a mix of α‐ and 3<jats:sub>10</jats:sub>‐helicity, while thio‐ and dithioether linkers produced less helicity. The lactam‐linked cyclic pentapeptide was also the most effective α‐helix nucleator attached to a 13‐residue model peptide.</jats:p>