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Glucose–Nucleobase Pseudo Base Pairs: Biomolecular Interactions within DNA
Author(s) -
VengutCliment Empar,
GómezPinto Irene,
Lucas Ricardo,
Peñalver Pablo,
Aviñó Anna,
Fonseca Guerra Célia,
Bickelhaupt F. Matthias,
Eritja Ramón,
González Carlos,
Morales Juan C.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201603510
Subject(s) - nucleobase , guanine , pyrimidine , chemistry , base pair , hydrogen bond , dna , stereochemistry , purine , crystallography , biochemistry , molecule , enzyme , nucleotide , organic chemistry , gene
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.