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Improved synthesis of 5-hydroxymethyl-2'-deoxycytidine phosphoramidite using a 2'-deoxyuridine to 2'-deoxycytidine conversion without temporary protecting groups |
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| Authors: | Hansen Anders S Thalhammer Armin El-Sagheer Afaf H Brown Tom Schofield Christopher J |
| Affiliation: | a Department of Chemistry and the Oxford Centre for Integrative Systems Biology, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, United Kingdom b School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, United Kingdom c Chemistry Branch, Department of Science and Mathematics, Faculty of Petroleum and Mining Engineering, Suez Canal University, Suez, Egypt |
| 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-HOMedC) 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-HOMedC phosphoramidite is obtained in six steps and 24% overall yield from 2′-deoxyuridine. |
| Keywords: | 5-Hydroxymethylcytosine DNA methylation DNA hydroxylation Epigenetics Phosphoramidite synthesis |
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