Synthesis of oligonucleotide inhibitors of DNA (Cytosine-C5) methyltransferase containing 5-azacytosine residues at specific sites.
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.
Güimil García
R
R
European Molecular Biology Laboratory, Heidelberg, Germany.
Brank
A S
AS
Christman
J K
JK
Marquez
V E
VE
Eritja
R
R
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*
D007202:Indicators and Reagents; D020319:Oligodeoxyribonucleotides, Antisense; C039854:5-azacytosine; D003596:Cytosine; D004248:DNA (Cytosine-5-)-Methyltransferases