DNAmod: 6-O-methylguanine

Description

A methylguanine in which the methyl group is positioned on the oxygen at position 6. Formed in DNA by alkylation of the oxygen atom of guanine, most often by N-nitroso compounds and sometimes due to methylation by other compounds such as endogenous S-adenosylmethionine, it base-pairs to thymine rather than cytidine, causing a G:C to A:T transition in DNA.

Chemical properties

Chemical formula	Net charge	Average mass
C6H7N5O	0	165.153

Recommended notation

Name	6-O-methylguanine
Abbreviation	m6G

Nomenclature

IUPAC	SMILES	InChI	InChIKey	Synonyms
6-methoxy-7H-purin-2-amine	COc1nc(N)nc2nc[nH]c12	InChI=1S/C6H7N5O/c1-12-5-3-4(9-2-8-3)10-6(7)11-5/h2H,1H3,(H3,7,8,9,10,11)	BXJHWYVXLGLDMZ-UHFFFAOYSA-N	o-(6)-methylguanine o(6)-methylguanine 6-methoxyguanine 6-methoxy-1h-purine-2-amine 2-amino-6-methoxypurine

Method	Method detail	Resolution	Qualifier	References
SMRT	direct detection	single-base	target sequences	Clark, TA, et al. 2011. Direct detection and sequencing of damaged DNA bases. Genome Integrity. 2.

Origin	Function	Functional detail	Organisms	References
natural	damage	highly cytotoxic	Escherichia colii Mesocricetus auratus Mus musculus Rattus norvegicus	Margison, GP, et al. 1976. Methylated purines in the deoxyribonucleic acid of various Syrian-golden-hamster tissues after administration of a hepatocarcinogenic dose of dimethylnitrosamine. The Biochemical Journal. 157(3). Frei, JV, et al. 1978. Alkylation of deoxyribonucleic acid in vivo in various organs of C57BL mice by the carcinogens N-methyl-N-nitrosourea, N-ethyl-N-nitrosourea and ethyl methanesulphonate in relation to induction of thymic lymphoma Some applications of high-pressure liquid chromatography. The Biochemical Journal. 174(3). Faustman-Watts, EM, et al. 1984. DNA-purine methylation in hepatic chromatin following exposure to dimethylnitrosamine or methylnitrosourea. Biochemical Pharmacology. 33(4). Mielecki, D, et al. 2014. Ada response - a strategy for repair of alkylated DNA in bacteria. FEMS Microbiology Letters. 355(1).

Database references:

CHEBI:20689

Citations

Clark, TA, et al. 2011. Direct detection and sequencing of damaged DNA bases. Genome Integrity. 2.
Faustman-Watts, EM, et al. 1984. DNA-purine methylation in hepatic chromatin following exposure to dimethylnitrosamine or methylnitrosourea. Biochemical Pharmacology. 33(4).
Frei, JV, et al. 1978. Alkylation of deoxyribonucleic acid in vivo in various organs of C57BL mice by the carcinogens N-methyl-N-nitrosourea, N-ethyl-N-nitrosourea and ethyl methanesulphonate in relation to induction of thymic lymphoma. Some applications of high-pressure liquid chromatography. The Biochemical Journal. 174(3).
Margison, GP, et al. 1976. Methylated purines in the deoxyribonucleic acid of various Syrian-golden-hamster tissues after administration of a hepatocarcinogenic dose of dimethylnitrosamine. The Biochemical Journal. 157(3).
Mielecki, D, et al. 2014. Ada response - a strategy for repair of alkylated DNA in bacteria. FEMS Microbiology Letters. 355(1).
Tan, NW, et al. 1990. Interaction of oligonucleotides containing 6-O-methylguanine with human DNA (cytosine-5-)-methyltransferase [published erratumm appears in Biochemistry 1992 Aug 4;31(30):7008]. Biochemistry. 29(39).
Wong, CW, et al. 1992. Structure-related properties of the mutagenic lesion 6-O-methylguanine in DNA. Journal of Molecular Biology. 228(4).
Wunschel, DS, et al. 2004. Proofreading activity of Pfu thermostable DNA polymerase on a 6-O-methylguanine-containing template monitored by ESI-FTICR mass spectrometry. Chembiochem : A European Journal of Chemical Biology. 5(7).