Format

Send to

Choose Destination
Angew Chem Int Ed Engl. 2016 Jul 18;55(30):8643-7. doi: 10.1002/anie.201603510. Epub 2016 Jun 22.

Glucose-Nucleobase Pseudo Base Pairs: Biomolecular Interactions within DNA.

Author information

1
Department of Bioorganic Chemistry, Instituto de Investigaciones Químicas, CSIC-Universidad de Sevilla, Américo Vespucio 49, 41092, 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, 18016, Armilla, Granada, Spain.
4
Instituto de Química Avanzada de Cataluña (IQAC), CSIC, CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine, 08034, Barcelona, Spain.
5
Department of Theoretical Chemistry and Amsterdam Center for Multiscale Modeling, Vrije Universiteit Amsterdam, 1081, HV, Amsterdam, The Netherlands.
6
Institute of Molecules and Materials (IMM), Radboud University, 6525, AJ, Nijmegen, The Netherlands.
7
Department of Bioorganic Chemistry, Instituto de Investigaciones Químicas, CSIC-Universidad de Sevilla, Américo Vespucio 49, 41092, Sevilla, Spain. jcmorales@ipb.csic.es.
8
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.

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; NMR spectroscopy; hydrogen bonds; noncovalent interactions; nucleobases

PMID:
27328804
DOI:
10.1002/anie.201603510
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for Wiley
Loading ...
Support Center