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Glucose–Nucleobase Pseudo Base Pairs: Biomolecular Interactions within DNA

IIQ

E. Vengut-Climent, I. Gómez-Pinto, R. Lucas, P. Peñalver, A. Aviñó, C. Fonseca Guerra, F. M. Bickelhaupt, R. Eritja, C. González, J.C. Morales Angew. Chem. Int. Ed. 2016, Vol. 55, 8643-8647. DOI: 10.1002/anie.201603510

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 itsOH 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-Apair.