title: Synthesis of oligonucleotide inhibitors of DNA (Cytosine-C5) methyltransferase containing 5-azacytosine residues at specific sites.
abstract: The incorporation of 5-azacytosine residues into DNA causes potent inhibition of DNA (Cytosine-C5) methyltransferases. The synthesis of oligodeoxyribonucleotides incorporating single or multiple 5-aza-2'-deoxycytidine residues at precise sites was undertaken to generate an array of sequences containing the reactive 5-azacytosine base as specific target sites for enzymatic methylation. Preparation of these modified oligonucleotides requires the use of 2-(p-nitrophenyl)ethyloxycarbonyl (NPEOC) groups for the protection of exocyclic amino functions. These groups are removed under mild conditions, thus avoiding conventional protocols that are detrimental to the integrity of the 5-azacytosine ring.
authors.affiliation: European Molecular Biology Laboratory, Heidelberg, Germany.
authors.forename: R
authors.initials: R
authors.lastname: Güimil García
authors.forename: A S
authors.initials: AS
authors.lastname: Brank
authors.forename: J K
authors.initials: JK
authors.lastname: Christman
authors.forename: V E
authors.initials: VE
authors.lastname: Marquez
authors.forename: R
authors.initials: R
authors.lastname: Eritja
mesh_terms: D001483:Base Sequence; D003596:Cytosine / Q000031:analogs & derivatives*; D004248:DNA (Cytosine-5-)-Methyltransferases / Q000037:antagonists & inhibitors*; D007202:Indicators and Reagents; D020319:Oligodeoxyribonucleotides, Antisense / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D007202:Indicators and Reagents; D020319:Oligodeoxyribonucleotides, Antisense; C039854:5-azacytosine; D003596:Cytosine; D004248:DNA (Cytosine-5-)-Methyltransferases