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Nucleic Acids Res. 2011 May;39(10):4419-26. doi: 10.1093/nar/gkr015. Epub 2011 Jan 19.

Crystal structure of a DNA containing the planar, phenoxazine-derived bi-functional spectroscopic probe C.

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1
Emerald BioStructures, Bainbridge Island, WA 98110, USA.

Abstract

Previously, we developed the deoxycytosine analog Ç (C-spin) as a bi-functional spectroscopic probe for the study of nucleic acid structure and dynamics using electron paramagnetic resonance (EPR) and fluorescence spectroscopy. To understand the effect of Ç on nucleic acid structure, we undertook a detailed crystallographic analysis. A 1.7 Å resolution crystal structure of Ç within a decamer duplex A-form DNA confirmed that Ç forms a non-perturbing base pair with deoxyguanosine, as designed. In the context of double-stranded DNA Ç adopted a planar conformation. In contrast, a crystal structure of the free spin-labeled base ç displayed a ∼ 20° bend at the oxazine linkage. Density function theory calculations revealed that the bent and planar conformations are close in energy and exhibit the same frequency for bending. These results indicate a small degree of flexibility around the oxazine linkage, which may be a consequence of the antiaromaticity of a 16-π electron ring system. Within DNA, the amplitude of the bending motion is restricted, presumably due to base-stacking interactions. This structural analysis shows that the Ç forms a planar, structurally non-perturbing base pair with G indicating it can be used with high confidence in EPR- or fluorescence-based structural and dynamics studies.

PMID:
21252294
PMCID:
PMC3105401
DOI:
10.1093/nar/gkr015
[Indexed for MEDLINE]
Free PMC Article
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