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dc.contributor.author | Blázquez-Sánchez, M. Teresa | - |
dc.contributor.author | Marcelo, Filipa | - |
dc.contributor.author | Fernández-Alonso, M. Carmen | - |
dc.contributor.author | Poveda, Ana | - |
dc.contributor.author | Jiménez-Barbero, Jesús | - |
dc.contributor.author | Vicent, Cristina | - |
dc.date.accessioned | 2015-05-27T09:49:19Z | - |
dc.date.available | 2015-05-27T09:49:19Z | - |
dc.date.issued | 2014 | - |
dc.identifier | doi: 10.1002/chem.201403911 | - |
dc.identifier | issn: 0947-6539 | - |
dc.identifier | e-issn: 1521-3765 | - |
dc.identifier.citation | Chemistry - A European Journal 20: 17640-17652 (2014) | - |
dc.identifier.uri | http://hdl.handle.net/10261/115785 | - |
dc.description.abstract | A strategy to create cooperative hydrogen-bonding centers by using strong and directional intramolecular hydrogen-bonding motifs that can survive in aqueous media is presented. In particular, glyco-oligoamides, a family of DNA minor groove binders, with cooperative and non-cooperative hydrogen-bonding donor centers in the carbohydrate residues have been designed, synthesized, and studied by means of NMR spectroscopy and molecular modeling methods. Indeed, two different sugar moieties, namely, β-D-Man-Py-γ-Py-Ind (1; Ind = indole, Man = mannose, Py= pyrrole) and β-D-Tal-Py-γ-Py-Ind (2; Tal = talose), were chosen according to our design. These sugar molecules should present oneor two-directional intramolecular hydrogen bonds. The challenge has been to study the conformation of the glyco-oligoamides at low temperature in physiological media by detecting the exchangeable protons (amide NH and OH resonances) by means of NMR spectroscopic analysis. In addition, two more glyco-oligoamides with non-cooperative hydrogen-bonding centers, that is, β-D-Glc-Py-γ-Py-Ind (3; Glc = glucose), β-D-Gal-Py-γ-Py-Ind (4; Gal = galac-tose), and the model compounds β-D-Man-Py-NHAc (5) and β-D-Tal-Py-NHAc (6) were synthesized and studied for comparison. We have demonstrated the existence of directional intramolecular hydrogen bonds in 1 and 2 in aqueous media. The unexpected differences in terms of stabilization of the intramolecular hydrogen bonds in 1 and 2 relative to 5 and 6 promoted us to evaluate the influence of CH-π interactions on the establishment of intramolecular hydrogen bonds by using computational methods. Initial binding studies of 1 and 2 with calf-thymus DNA and poly(dA-dT)2 by NMR spectroscopic analysis and molecular dynamics simulations were also carried out. Both new sugar-oligoamides are bound in the minor groove of DNA, thus keeping a stable hairpin structure, as in the free state, in which both intramolecular hydrogen-bonding and CH-π interactions are present. | - |
dc.publisher | John Wiley & Sons | - |
dc.rights | closedAccess | - |
dc.subject | Cooperativity | - |
dc.subject | Hydrogen bonds | - |
dc.subject | Pi interactions | - |
dc.subject | Carbohydrates | - |
dc.subject | DNA | - |
dc.title | Cooperative hydrogen bonding in glyco-oligoamides: DNA minor groove binders in aqueous media | - |
dc.type | artículo | - |
dc.identifier.doi | 10.1002/chem.201403911 | - |
dc.date.updated | 2015-05-27T09:49:19Z | - |
dc.description.version | Peer Reviewed | - |
dc.language.rfc3066 | eng | - |
dc.type.coar | http://purl.org/coar/resource_type/c_6501 | es_ES |
item.cerifentitytype | Publications | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.grantfulltext | none | - |
item.openairetype | artículo | - |
item.fulltext | No Fulltext | - |
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