Syntheses of 5-Formyl- and 5-Carboxyl-dC Containing DNA Oligos as Potential Oxidation Products of 5-Hydroxymethylcytosine in DNA
- 7 June 2011
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 13 (13), 3446-3449
- https://doi.org/10.1021/ol201189n
Abstract
To investigate the potential oxidation products of 5-hydroxymethylcytosine (5-hmC)-containing DNA, we present here efficient syntheses of 5-formyl- and 5-methoxycarbonyl-2′-deoxycytidine phosphoramidites. The 5-formyl group in III was easy to introduce and was compatible with phosphoramidite and DNA syntheses. An additional treatment of ODN1 with NaBH4 produced the corresponding ODN2 quantitatively. Phosphoramidite V was also incorporated into DNA, and the methyl ester could be hydrolyzed under mild basic conditions to afford ODN3.Keywords
This publication has 15 references indexed in Scilit:
- Syntheses of Two 5-Hydroxymethyl-2′-deoxycytidine Phosphoramidites with TBDMS as the 5-Hydroxymethyl Protecting Group and Their Incorporation into DNAThe Journal of Organic Chemistry, 2011
- Selective chemical labeling reveals the genome-wide distribution of 5-hydroxymethylcytosineNature Biotechnology, 2011
- Epigenetic Reprogramming in Plant and Animal DevelopmentScience, 2010
- Role of Tet proteins in 5mC to 5hmC conversion, ES-cell self-renewal and inner cell mass specificationNature, 2010
- Sensitive enzymatic quantification of 5-hydroxymethylcytosine in genomic DNANucleic Acids Research, 2010
- Quantification of the Sixth DNA Base Hydroxymethylcytosine in the BrainAngewandte Chemie-International Edition, 2010
- Mammalian cytosine methylation at a glanceJournal of Cell Science, 2009
- Conversion of 5-Methylcytosine to 5-Hydroxymethylcytosine in Mammalian DNA by MLL Partner TET1Science, 2009
- The Nuclear DNA Base 5-Hydroxymethylcytosine Is Present in Purkinje Neurons and the BrainScience, 2009
- Synthesis and investigation of the 5-formylcytidine modified, anticodon stem and loop of the human mitochondrial tRNAMetNucleic Acids Research, 2008