title: Efficient synthesis of 5-hydroxymethylcytosine containing DNA.
abstract: 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.
authors.affiliation: Center for Integrated Protein Science, Department of Chemistry, Ludwig-Maximilians-University Munich, Butenandtstr. 5-13, 81377 Munich, Germany.
authors.forename: Martin
authors.initials: M
authors.lastname: Münzel
authors.forename: Daniel
authors.initials: D
authors.lastname: Globisch
authors.forename: Christian
authors.initials: C
authors.lastname: Trindler
authors.forename: Thomas
authors.initials: T
authors.lastname: Carell
mesh_terms: D044503:5-Methylcytosine / Q000031:analogs & derivatives; D000818:Animals; D003596:Cytosine / Q000031:analogs & derivatives* / Q000737:chemistry; D004247:DNA / Q000138:chemical synthesis*; D016678:Genome; D015394:Molecular Structure
chemical_list: C011865:5-hydroxymethylcytosine; D044503:5-Methylcytosine; D003596:Cytosine; D004247:DNA