Glucose–Nucleobase Pseudo Base Pairs: Biomolecular Interactions within DNA

Noncovalent forces rule the interactions between biomolecules. Inspired by a biomolecular interaction found in aminoglycoside–RNA recognition, glucose-nucleobase pairs have been examined. Deoxyoligonucleotides with a 6-deoxyglucose insertion are able to hybridize with their complementary strand, thu...

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Detalles Bibliográficos
Autores: Vengut Climent, Empar, Gómez Pinto, Irene, Lucas Rodríguez, Ricardo, Peñalver, Pablo, Aviñó, Anna, Fonseca Guerra, Célia, Bickelhaupt, F. Matthias, Eritja, Ramón, González, Carlos, Morales, Juan C.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2016
País:España
Institución:Universidad de Sevilla (US)
Repositorio:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/135179
Acceso en línea:https://hdl.handle.net/11441/135179
https://doi.org/10.1002/anie.201603510
Access Level:acceso abierto
Palabra clave:DNA
Hydrogen bonds
NMR spectroscopy
Noncovalent interactions
Nucleobases
Descripción
Sumario:Noncovalent forces rule the interactions between biomolecules. Inspired by a biomolecular interaction found in aminoglycoside–RNA recognition, glucose-nucleobase pairs have been examined. Deoxyoligonucleotides with a 6-deoxyglucose insertion are able to hybridize with their complementary strand, thus exhibiting a preference for purine nucleobases. Although the resulting double helices are less stable than natural ones, they present only minor local distortions. 6-Deoxyglucose stays fully integrated in the double helix and its OH groups form two hydrogen bonds with the opposing guanine. This 6-deoxyglucose-guanine pair closely resembles a purine-pyrimidine geometry. Quantum chemical calculations indicate that glucose-purine pairs are as stable as a natural T-A pair.