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5-Hydroxymethylcytosine has recently been characterized as the 'sixth base' in human DNA. To enable research on this DNA modification, we report an improved method for the synthesis of 5-hydroxymethyl-2'-deoxycytidine ((5-HOMe)dC) phosphoramidite for site-specific incorporation into oligonucleotides. To minimize manipulations we employed a temporary protecting group-free 2'-deoxyuridine to 2'-deoxycytidine conversion procedure that utilizes phase transfer catalysis. The desired (5-HOMe)dC phosphoramidite is obtained in six steps and 24% overall yield from 2'-deoxyuridine.

Original publication

DOI

10.1016/j.bmcl.2010.12.098

Type

Journal article

Journal

Bioorg Med Chem Lett

Publication Date

15/02/2011

Volume

21

Pages

1181 - 1184

Keywords

Deoxycytidine, Deoxyuridine, Electrophoresis, Capillary, Humans, Oligonucleotides, Organophosphorus Compounds, Spectrometry, Mass, Electrospray Ionization