A route to RNA with an alkylating group at the 5'-triphosphate residue.
Reaction of ATP with N,N,N'-tris(2-chloroethyl), N' (p-formyl-phenyl)propylenediamine-1,3 (abbreviation C13R) afforded a gamma-ester of ATP (abbreviation C1RpppA) - the product of alkylation by an aliphatic nitrogen mustard residue of C13R. The alkylating activity of the aromatic nitrogen mustard residue of C1RpppA is suppressed by the electron-acceptor effect of the p-formyl group. C1RpppA is a substrate of RNA-polymerase, and affords RNA with C1RpppA-residues at the 5'-termini.
D000255:Adenosine Triphosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000477:Alkylating Agents; D055598:Chemical Phenomena; D002621:Chemistry; D002848:Chromatography, DEAE-Cellulose; D002852:Chromatography, Ion Exchange; D012321:DNA-Directed RNA Polymerases / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D009588:Nitrogen Mustard Compounds; D012313:RNA / Q000378:metabolism*; D013056:Spectrophotometry, Ultraviolet
D000477:Alkylating Agents; D009588:Nitrogen Mustard Compounds; D012313:RNA; C020534:N,N,N'-tri(beta-chloroethyl)-N'-(4-formylphenyl)-1,3-propylenediamine; C027719:ClRpppA; D000255:Adenosine Triphosphate; D012321:DNA-Directed RNA Polymerases