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Glucose-Nucleobase Pseudo Base Pairs: Biomolecular Interactions within DNA

AuthorsVengut-Climent, Empar; Gomez-Pinto, Irene ; Lucas, Ricardo ; Peñalver, Pablo ; Aviñó, Anna; Fonsecaguerra, Célia; Bickelhaupt, F. Matthias; Eritja Casadellà, Ramón; Bustamante González, Carlos Alberto; Morales, Juan Carlos
Hydrogen bonds
NMR spectroscopy
Noncovalent interactions
Issue Date2016
PublisherJohn Wiley & Sons
CitationAngewandte Chemie - International Edition 2016
AbstractNoncovalent 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. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publisher version (URL)http://dx.doi.org/10.1002/anie.201603510
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