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Int. J. Mol. Sci. 2013, 14(3), 5765-5774; doi:10.3390/ijms14035765
Article

Quick, Selective and Reversible Photocrosslinking Reaction between 5-Methylcytosine and 3-Cyanovinylcarbazole in DNA Double Strand

1,2,* , 1
 and
1
Received: 20 December 2012 / Revised: 12 February 2013 / Accepted: 26 February 2013 / Published: 12 March 2013
(This article belongs to the Special Issue Molecular Cut and Paste)
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Abstract

Selective photocrosslinking reaction between 3-cyanovinylcarbazole nucleoside (CNVK) and 5-methylcytosine (mC), which is known as epigenetic modification in genomic DNA, was developed. The reaction was completely finished within 5 s of 366 nm irradiation, and the rate of this photocrosslinking reaction was ca. 30-fold higher than that in the case of unmodified normal cytosine. There were no significant differences in the thermodynamic parameters and the kinetics of hybrid formation of oligonucleotide (ODN) containing CNVK and its complementary ODN containing C or mC at the photocrosslinking site, and suggesting that the quick and selective photoreaction has potential for the selective detection of mC in the DNA strand via the photocrosslinking reaction.
Keywords: photocrosslinking; 5-methylcytosine; 3-cyanovinylcarbazole nucleoside photocrosslinking; 5-methylcytosine; 3-cyanovinylcarbazole nucleoside
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Fujimo, K.; Konishi-Hiratsuka, K.; Sakamoto, T. Quick, Selective and Reversible Photocrosslinking Reaction between 5-Methylcytosine and 3-Cyanovinylcarbazole in DNA Double Strand. Int. J. Mol. Sci. 2013, 14, 5765-5774.

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