Structural study of four-stranded quadruplex structures containing 2'-deoxy-8+ (propyn-1-yl)adenosine

In this paper, we report the NMR structural study of two quadruplex structures formed by truncations of the human telomeric sequence and containing a modified base, namely d(AprGGGT) and d(TAprGGGT), where Apr indicates 2'-deoxy-8-(propyn-1-yl)adenosines. Both oligonucleotides have been found t...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2004-03, Vol.12 (5), p.1191-1197
Main Authors: ESPOSITO, Veronica, RANDAZZO, Antonio, GALEONE, Aldo, VARRA, Michela, MAYOL, Luciano
Format: Article
Language:English
Subjects:
Base Sequence
Biological and medical sciences
Deoxyadenosines - chemistry
DNA - chemistry
Drug Stability
G-Quadruplexes
Guanine
Hydrogen Bonding
Medical sciences
Miscellaneous
Models, Molecular
Nucleic Acid Conformation
Oligodeoxyribonucleotides - chemistry
Pharmacology. Drug treatments
Temperature
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Summary:In this paper, we report the NMR structural study of two quadruplex structures formed by truncations of the human telomeric sequence and containing a modified base, namely d(AprGGGT) and d(TAprGGGT), where Apr indicates 2'-deoxy-8-(propyn-1-yl)adenosines. Both oligonucleotides have been found to form 4-fold symmetric G-quadruplex structures with all strands parallel and equivalent to each other and characterized by higher thermal stabilities than the natural counterparts. The presence of the propynyl groups affects the conformations of the 5' edge of both quadruplexes in such a way to prevent the formation of one of the two possible H-bond patterns observed for a canonical A-tetrad. The increased thermal stabilities of the modified quadruplexes seem to be mostly due to a prevalent syn glycosidic conformation assumed by the Apr residues.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2003.11.019