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

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 pho...

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Publication status:
Published

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Publisher copy:
10.1016/j.bmcl.2010.12.098

Authors


Hansen, AS More by this author
Thalhammer, A More by this author
El-Sagheer, AH More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
Bioorganic and medicinal chemistry letters
Volume:
21
Issue:
4
Pages:
1181-1184
Publication date:
2011-02-05
DOI:
EISSN:
1464-3405
ISSN:
0960-894X
URN:
uuid:c69533aa-20e9-45f1-ba7d-cedeb509fee0
Source identifiers:
115704
Local pid:
pubs:115704

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