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Org Lett. 2011 Jul 1;13(13):3446-9. doi: 10.1021/ol201189n. Epub 2011 Jun 7.

Syntheses of 5-formyl- and 5-carboxyl-dC containing DNA oligos as potential oxidation products of 5-hydroxymethylcytosine in DNA.

Author information

1
Department of Chemistry and Institute for Biophyscial Dynamics, The University of Chicago, 929 East 57th Street, Chicago, Illinois 60637, USA. daiqing@uchicago.edu

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 NaBH(4) 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.

PMID:
21648398
PMCID:
PMC3150843
DOI:
10.1021/ol201189n
[Indexed for MEDLINE]
Free PMC Article

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