A One Step Synthesis of O⁶-Methyl-2′-deoxyguanosine

The synthesis of oligoribonucleotides containing O6-methylguanosine: the role of conserved guanosine residues in hammerhead ribozyme cleavage

“…The latter compounds require further conversion into the 6-trimethylamino-(21, 29) or the 6-Nmethylpyrrolo-(30, 31) derivatives in order to effect displacement by methoxide ion. With the exception of the diazomethane treatment of (deoxy)nucleosides which gives rise to extensive side products that include N7-methyland N'-methyl-(deoxy)guanosines (24,25), no direct route to the synthesis of 06alkyl guanosine or deoxyguanosine has been reported.…”

An Overview of Chemical Processes That Damage Cellular DNA: Spontaneous Hydrolysis, Alkylation, and Reactions with Radicals

“…Alkylation at the exocyclic nitrogen atoms N 2 G, N 6 A, and N 4 C, the amidic nitrogens at N1-G and N1-T, and the oxygens at O 6 -G and O 4 -T yield chemically stable adducts (Figure ) − . Special attention has been paid to the O 6 -G and O 4 -T adducts because these reactions alter the Watson−Crick hydrogen-bonding faces of these bases and cause miscoding and mutagenesis during DNA replication − .…”

The Chemical Reactions of DNA Damage and Degradation

“…Alkylation at several sites on the DNA bases affords an attachment that is chemically stable. Nucleophilic sites that typically yield stable alkyl attachments include the exocyclic nitrogen atoms N 2 G, N 6 A, N 6 C, the amide-type nitrogens N1G, N1T, 0 6 G, and 0 4 T. [45][46][47][48][49][50][51][52] Alkyl groups on phosphate residues in DNA are typically stable under physiological conditions, 53,54 although the charge-neutralized phosphotriester groups are somewhat more prone to hydrolysis under basic conditions, compared with the native phosphodiesters. 55,56 POSSIBLE FATES OF ALKYLATED DNA…”