title: Synthesis of a DNA promoter segment containing all four epigenetic nucleosides: 5-methyl-, 5-hydroxymethyl-, 5-formyl-, and 5-carboxy-2'-deoxycytidine.
abstract: A 5-formyl-2'-deoxycytidine (fdC) phosphoramidite building block that enables the synthesis of fdC-containing DNA with excellent purity and yield has been developed. In combination with phosphoramidites for 5-methyl-dC, 5-hydroxymethyl-dC, and carboxy-dC, it was possible to prepare a segment of the OCT-4 promoter that contains all four epigenetic bases. Because of the enormous interest in these new epigenetic bases, the ability to insert all four of them into DNA should be of great value for the scientific community.
authors.affiliation: Center for Integrated Protein Science, Department für Chemie, Ludwig-Maximilians-Universität, Butenandtstrasse 5-13, 81377 München (Germany) http://www.carellgroup.de.
authors.forename: Arne S
authors.initials: AS
authors.lastname: Schröder
authors.forename: Jessica
authors.initials: J
authors.lastname: Steinbacher
authors.forename: Barbara
authors.initials: B
authors.lastname: Steigenberger
authors.forename: Felix A
authors.initials: FA
authors.lastname: Gnerlich
authors.forename: Stefan
authors.initials: S
authors.lastname: Schiesser
authors.forename: Toni
authors.initials: T
authors.lastname: Pfaffeneder
authors.forename: Thomas
authors.initials: T
authors.lastname: Carell
mesh_terms: D004247:DNA / Q000138:chemical synthesis*; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D044127:Epigenesis, Genetic; D015394:Molecular Structure; D009705:Nucleosides / Q000235:genetics*
chemical_list: C402104:5-formyl-2'-deoxycytidine; D009705:Nucleosides; D003841:Deoxycytidine; D004247:DNA
keywords: 5-formylcytosine; DNA methylation; epigenetics; oligonucleotides; solid-phase synthesis