title: Glucose-Nucleobase Pseudo Base Pairs: Biomolecular Interactions within DNA.
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.
authors.affiliation: Department of Bioorganic Chemistry, Instituto de Investigaciones Químicas, CSIC-Universidad de Sevilla, Américo Vespucio 49, 41092, Sevilla, Spain.
authors.forename: Empar
authors.initials: E
authors.lastname: Vengut-Climent
authors.affiliation: Instituto de Química Física "Rocasolano", CSIC, 28006, Madrid, Spain.
authors.forename: Irene
authors.initials: I
authors.lastname: Gómez-Pinto
authors.affiliation: Department of Bioorganic Chemistry, Instituto de Investigaciones Químicas, CSIC-Universidad de Sevilla, Américo Vespucio 49, 41092, Sevilla, Spain.|Department of Biochemistry and Molecular Pharmacology, Instituto de Parasitología y Biomedicina, CSIC, Parque Tecnológico Ciencias de la Salud, 18016, Armilla, Granada, Spain.
authors.forename: Ricardo
authors.initials: R
authors.lastname: Lucas
authors.affiliation: Department of Bioorganic Chemistry, Instituto de Investigaciones Químicas, CSIC-Universidad de Sevilla, Américo Vespucio 49, 41092, Sevilla, Spain.|Department of Biochemistry and Molecular Pharmacology, Instituto de Parasitología y Biomedicina, CSIC, Parque Tecnológico Ciencias de la Salud, 18016, Armilla, Granada, Spain.
authors.forename: Pablo
authors.initials: P
authors.lastname: Peñalver
authors.affiliation: Instituto de Química Avanzada de Cataluña (IQAC), CSIC, CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine, 08034, Barcelona, Spain.
authors.forename: Anna
authors.initials: A
authors.lastname: Aviñó
authors.affiliation: Department of Theoretical Chemistry and Amsterdam Center for Multiscale Modeling, Vrije Universiteit Amsterdam, 1081, HV, Amsterdam, The Netherlands.
authors.forename: Célia
authors.initials: C
authors.lastname: Fonseca Guerra
authors.affiliation: Department of Theoretical Chemistry and Amsterdam Center for Multiscale Modeling, Vrije Universiteit Amsterdam, 1081, HV, Amsterdam, The Netherlands.|Institute of Molecules and Materials (IMM), Radboud University, 6525, AJ, Nijmegen, The Netherlands.
authors.forename: F Matthias
authors.initials: FM
authors.lastname: Bickelhaupt
authors.affiliation: Instituto de Química Avanzada de Cataluña (IQAC), CSIC, CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine, 08034, Barcelona, Spain.
authors.forename: Ramón
authors.initials: R
authors.lastname: Eritja
authors.affiliation: Instituto de Química Física "Rocasolano", CSIC, 28006, Madrid, Spain.
authors.forename: Carlos
authors.initials: C
authors.lastname: González
authors.affiliation: Department of Bioorganic Chemistry, Instituto de Investigaciones Químicas, CSIC-Universidad de Sevilla, Américo Vespucio 49, 41092, Sevilla, Spain. jcmorales@ipb.csic.es.|Department of Biochemistry and Molecular Pharmacology, Instituto de Parasitología y Biomedicina, CSIC, Parque Tecnológico Ciencias de la Salud, 18016, Armilla, Granada, Spain. jcmorales@ipb.csic.es.
authors.forename: Juan C
authors.identifier: 0000-0003-2400-405X
authors.initials: JC
authors.lastname: Morales
mesh_terms: D020029:Base Pairing; D004247:DNA / Q000737:chemistry / Q000378:metabolism*; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D006147:Guanine / Q000737:chemistry / Q000378:metabolism; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D009699:N-Glycosyl Hydrolases / Q000737:chemistry / Q000378:metabolism*; D009690:Nucleic Acid Conformation; D010303:Paromomycin / Q000737:chemistry / Q000378:metabolism; D011789:Quantum Theory; D013816:Thermodynamics; D044366:Transition Temperature
chemical_list: D006147:Guanine; D010303:Paromomycin; D004247:DNA; D003847:Deoxyglucose; D009699:N-Glycosyl Hydrolases; C030681:purine nucleosidase; C037904:6-deoxyglucose
keywords: DNA; NMR spectroscopy; hydrogen bonds; noncovalent interactions; nucleobases