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Título

Disulfide bonds versus Trp···Trp pairs in irregular β-hairpins: NMR structure of vammin loop 3-derived peptides as a case study

AutorMirassou, Yasmina ; Santiveri, Clara M.; Pérez de Vega, M. Jesús; González-Muñiz, Rosario ; Jiménez, M. Angeles
Palabras claveBeta hairpin
Circular dichroism
Disulfide bonds
NMR spectroscopy
Peptides
Trp-Trp interactions
Fecha de publicación17-mar-2009
EditorJohn Wiley & Sons
CitaciónChembiochem 10(5): 902-910 (2009)
ResumenWhere a noncovalent interaction is better than a covalent bond: The most stabilising cross-strand pairs were incorporated into an irregular β-hairpin, loop 3 of vammin. 1H and 13C NMR conformational analyses of these designed peptides indicated that an edge-to-face Trp···Trp interaction leads to a β-hairpin that is more stable than a disulfide bond.
Structural studies on model peptides have led to a good understanding of the rules behind the formation and stability of regular β-hairpins. To test their applicability to the successful design of irregular β-hairpins with long loops and/or β-bulges at the strands, we mimicked loop 3 of vammin, a 4:6 β-hairpin with a non-Gly β-bulge. The most stabilising cross-strand pairs, disulfide bonds or/and Trp···Trp pairs, were incorporated at non-hydrogen-bonded sites in peptides spanning the 69-80 region of vammin. According to NMR data, these modified peptides adopt β-hairpin conformations as intended by design. The Trp-containing peptides reproduce even the unusual positive φ angle for the Gln residue, with the indole rings in the preferred edge-to-face orientation. For the first time the β-hairpin-stabilising capacities of a disulfide bond and a Trp···Trp pair are compared in the same model system. We found that the contribution to stability of the noncovalent indole-indole interaction is larger than that of the covalent disulfide bond, and that their combination gives rise to an even more stable β-hairpin.
Descripción9 pages, 6 figures, 1 table.-- PMID: 19294654 [PubMed].-- Supporting information (Suppl. figs SF1-SF2, tabs ST1-ST2) available at: http://www3.interscience.wiley.com/cgi-bin/fulltext/122264837/sm001.pdf?PLACEBO=IE.pdf
Versión del editorhttp://dx.doi.org/10.1002/cbic.200800834
URIhttp://hdl.handle.net/10261/13199
DOI10.1002/cbic.200800834
ISSN1439-4227
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