Epigenetic Tools

Novel phosphoramidites of the new epigenetic cytosin bases

To study the function of the epigenetically important bases (1-4) it is of utmost importance to have efficient methods that enable the synthesis of DNA oligomers containing the epigenetic bases at defined sequence positions.
Since 2010, the Carell Group is involved in developing phosphoramidites of the epigenetic bases which couple with superior efficiency. Our new building blocks provide DNA in excellent purity with unrivaled yields. Furthermore, no side reactions are observed and mild deprotection conditions prevent oxidative or reductive lesions.

1. hmdC phosphoramidite

M. Münzel, D. Globisch, C. Trindler, T. Carell, Org Lett. 2010, 12, 5671-5673.
Efficient Synthesis of 5-Hydroxymethylcytosine Containing DNA

Phosphoramidite 8 is available from GlenResearch (5-Hydroxymethyl-dC-CE Phosphoramidite).

2. fdC phosphoramidite

A.S. Schröder, J. Steinbacher, B. Steigenberger, F.A. Gnerlich, S. Schiesser, T. Pfaffeneder, T. Carell, Angew Chem Int Ed Engl. 2014, 53, 315-8 (selected as Hot-Paper)
Synthesis of a DNA Promoter Segment Containing All Four Epigenetic Nucleosides: 5-Methyl-, 5-Hydroxymethyl-, 5-Formyl-, and 5-Carboxy-2’-Deoxycytidine

Phosphoramidite 12 is available from GlenResearch (5-Formyl-dC-CE Phosphoramidite).

3. cadC phosphoramidite

M. Münzel, U. Lischke, D. Stathis, T. Pfaffeneder, F. A. Gnerlich, C. A. Deiml, S. C. Koch, K. Karaghiosoff, T. Carell
Chemistry. 2011, 17, 13782-13788.
Improved Synthesis and Mutagenicity of Oligonucleotides Containing 5-Hydroxymethylcytosine, 5-Formylcytosine and 5-Carboxylcytosine.