Facile synthesis of hydroxymethylcytosine-containing oligonucleotides and their reactivity upon osmium oxidation.

DNA strands containing a 5-hydroxymethylcytosine ((hm)C), which have recently been found in neuron cells and embryonic stem cells, were synthesized through a facile synthetic technique. The (hm)C-containing strands were efficiently oxidized at (hm)C using an osmium oxidation assay. The (hm)C was oxidized as easily as 5-methylcytosine, which can be distinguished from unmethylated cytosine.

[1]  David R. Liu,et al.  The Behaviour of 5-Hydroxymethylcytosine in Bisulfite Sequencing , 2010, PloS one.

[2]  S. Ikeda,et al.  Doubly thiazole orange-labeled cytidine for functional expansion of a hybridization-sensitive probe , 2009 .

[3]  N. Heintz,et al.  The Nuclear DNA Base 5-Hydroxymethylcytosine Is Present in Purkinje Neurons and the Brain , 2009, Science.

[4]  David R. Liu,et al.  Conversion of 5-Methylcytosine to 5- Hydroxymethylcytosine in Mammalian DNA by the MLL Partner TET1 , 2009 .

[5]  Kazuki Tainaka,et al.  Osmium complexation of mismatched DNA: effect of the bases adjacent to mismatched 5-methylcytosine. , 2009, Bioconjugate chemistry.

[6]  A. Okamoto Chemical approach toward efficient DNA methylation analysis. , 2009, Organic & biomolecular chemistry.

[7]  A. Okamoto,et al.  Synthesis and characterization of the 5-methyl-2'-deoxycytidine glycol-dioxoosmium-bipyridine ternary complex in DNA. , 2008, Organic & biomolecular chemistry.

[8]  Kazuki Tainaka,et al.  An osmium-DNA interstrand complex: application to facile DNA methylation analysis. , 2007, Journal of the American Chemical Society.

[9]  Kazuki Tainaka,et al.  Direct labeling of 5-methylcytosine and its applications. , 2007, Journal of the American Chemical Society.

[10]  Kazuki Tainaka,et al.  Sequence-selective osmium oxidation of DNA: efficient distinction between 5-methylcytosine and cytosine. , 2006, Organic & biomolecular chemistry.

[11]  J. H. Boom,et al.  Chemical and Enzymatic Synthesis of DNA Fragments Containing 5‐(β‐D‐Glucopyranosyloxymethyl)‐2′‐deoxycytidine − a Modified Nucleoside in T4 Phage DNA , 2001 .

[12]  L. Sowers,et al.  Solid phase synthesis and restriction endonuclease cleavage of oligodeoxynucleotides containing 5-(hydroxymethyl)-cytosine. , 1997, Nucleic acids research.

[13]  L. E. McDonald,et al.  A genomic sequencing protocol that yields a positive display of 5-methylcytosine residues in individual DNA strands. , 1992, Proceedings of the National Academy of Sciences of the United States of America.

[14]  B. Froehler,et al.  Dialkylformamidines: depurination resistant N6-protecting group for deoxyadenosine. , 1983, Nucleic acids research.

[15]  H. Hayatsu,et al.  Bisulfite modification of nucleic acids and their constituents. , 1976, Progress in nucleic acid research and molecular biology.