Formation of a pseudo-β-hairpin motif utilizing the Ant-Pro reverse turn: consequences of stereochemical reordering

Herein, we report a special case of pseudo-β-hairpin formation by tetrapetide sequences featuring a two-membered Ant-Pro dipeptide motif (Ant = anthranilic acid and Pro = proline) at the loop region. These folded structures uniquely feature the presence of C9- and C17-H-bonding patterns at reverse t...

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Veröffentlicht in:	Organic & biomolecular chemistry 2014-02, Vol.12 (5), p.774-782
Hauptverfasser:	Nair, Roshna V, Kotmale, Amol S, Dhokale, Snehal A, Gawade, Rupesh L, Puranik, Vedavadi G, Rajamohanan, Pattuparambil R, Sanjayan, Gangadhar J
Format:	Artikel
Sprache:	eng
Schlagworte:	Dimerization Dipeptides - chemical synthesis Dipeptides - chemistry Hydrogen Bonding Models, Molecular Protein Structure, Secondary Stereoisomerism
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Zusammenfassung:	Herein, we report a special case of pseudo-β-hairpin formation by tetrapetide sequences featuring a two-membered Ant-Pro dipeptide motif (Ant = anthranilic acid and Pro = proline) at the loop region. These folded structures uniquely feature the presence of C9- and C17-H-bonding patterns at reverse turn and interstrand regions, respectively. Their hairpin nucleation and folding propensities have been expounded using solution and solid state studies of distinct stereochemically altered sequences.
ISSN:	1477-0520 1477-0539
DOI:	10.1039/c3ob42016g