Published in

Wiley-VCH Verlag, ChemInform, 26(42), p. no-no, 2011

DOI: 10.1002/chin.201126186

Elsevier, Bioorganic and Medicinal Chemistry Letters, 4(21), p. 1181-1184

DOI: 10.1016/j.bmcl.2010.12.098

Links

Tools

Export citation

Search in Google Scholar

Improved synthesis of 5-hydroxymethyl-2′-deoxycytidine phosphoramidite using a 2′-deoxyuridine to 2′-deoxycytidine conversion without temporary protecting groups

Journal article published in 2011 by Anders S. Hansen, Armin Thalhammer, Afaf H. El-Sagheer, Tom Brown ORCID, Christopher J. Schofield
This paper is available in a repository.
This paper is available in a repository.

Full text: Download

Red circle
Preprint: archiving forbidden
Orange circle
Postprint: archiving restricted
Upload
Red circle
Published version: archiving forbidden
Policy details
Data provided by SHERPA/RoMEO

Abstract

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.