Glucose–Nucleobase Pseudo Base Pairs: Biomolecular Interactions within DNA. Issue 30 (22nd June 2016)

• Record Type: Journal Article
• Authors: Vengut‐Climent, Empar; Gómez‐Pinto, Irene; Lucas, Ricardo; Peñalver, Pablo; Aviñó, Anna; Fonseca Guerra, Célia; Bickelhaupt, F. Matthias; Eritja, Ramón; González, Carlos; Morales, Juan C.
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 30(2016)
• Page Start: 8643
• Page End: 8647
• Publication Date: 2016-06-22
• Subjects: DNA -- hydrogen bonds -- NMR spectroscopy -- noncovalent interactions -- nucleobases; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201603510
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : New lego pieces : The formation of a glucose–nucleobase pseudo base pair is proposed as a new type of biomolecular interaction. When formed within a DNA double helix, the high‐resolution structure shows only a minor distortion. These DNA duplexes are less stable than natural ones, but glucose shows a preference for binding purine nucleobases. Moreover, quantum chemical calculations indicate that glucose–purine pairs are as stable as a natural T–A pair.