Glucose–Nucleobase Pseudo Base Pairs: Biomolecular Interactions within DNA. (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. Volume 128:Number 30(2016)
• Page Start: 8785
• Page End: 8789
• Publication Date: 2016-06-22
• Subjects: DNA -- Nichtkovalente Wechselwirkungen -- NMR-Spektroskopie -- Nucleobasen -- Wasserstoffbrücken; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201603510
• Languages: English
• ISSNs: 0044-8249

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.