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Glucose–Nucleobase Pseudo Base Pairs: Biomolecular Interactions within DNA |
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| Authors: | Dr Empar Vengut‐Climent Dr Irene Gómez‐Pinto Dr Ricardo Lucas Dr Pablo Peñalver Dr Anna Aviñó Dr Célia Fonseca Guerra Prof Dr F Matthias Bickelhaupt Prof Ramón Eritja Prof Carlos González Dr Juan C Morales |
| Institution: | 1. Department of Bioorganic Chemistry, Instituto de Investigaciones Químicas, CSIC—Universidad de Sevilla, Sevilla, Spain;2. Instituto de Química Física “Rocasolano”, CSIC, 28006, Madrid, Spain;3. Department of Biochemistry and Molecular Pharmacology, Instituto de Parasitología y Biomedicina, CSIC, Parque Tecnológico Ciencias de la Salud, Armilla, Granada, Spain;4. Instituto de Química Avanzada de Catalu?a (IQAC), CSIC, CIBER—BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona, Spain;5. Department of Theoretical Chemistry and Amsterdam Center for Multiscale Modeling, Vrije Universiteit Amsterdam, HV, Amsterdam, The Netherlands;6. Institute of Molecules and Materials (IMM), Radboud University, AJ, Nijmegen, The Netherlands |
| Abstract: | 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. |
| Keywords: | DNA hydrogen bonds NMR spectroscopy noncovalent interactions nucleobases |