Efficient Synthesis of 5-Hydroxymethylcytosine Containing DNA

Mu╠łnzel M, Globisch D, Trindler C, Carell T

Org. Lett. 12 (24) 5671-5673 [2010-12-17; online 2010-12-17]

5-Hydroxymethylcytosine ((5-HOMe)dC) was recently discovered as the sixth base in the mammalian genome. The development of a new phosphoramidite building block is reported, which allows efficient synthesis of (5-HOMe)dC containing DNA. Key steps of the synthesis are a palladium-catalyzed formylation and the simultaneous protection of a hydroxyl and amino group as a cyclic carbamate. DNA synthesis is possible under standard conditions, and deprotection can be carried out with dilute NaOH.

Daniel Globisch

SciLifeLab Fellow

PubMed 21082782

DOI 10.1021/ol102408t

Crossref 10.1021/ol102408t

Publications 9.5.0