DNAmod: 6-methyladenine

Description

A methyladenine that is 9H-purin-6-amine substituted by a methyl group at the amino nitrogen.

Chemical properties

Chemical formula	Net charge	Average mass
C6H7N5	0	149.15330

Recommended notation

Name	6-methyladenine
Abbreviation	6mA
Symbol	a

Nomenclature

IUPAC	SMILES	InChI	InChIKey	Synonyms
N-methyl-9H-purin-6-amine	CNc1ncnc2[nH]cnc12	InChI=1S/C6H7N5/c1-7-5-4-6(10-2-8-4)11-3-9-5/h2-3H,1H3,(H2,7,8,9,10,11)	CKOMXBHMKXXTNW-UHFFFAOYSA-N	6-methylaminopurine n6-methyladenine 6-map n6-monomethyladenine

Mapping techniques

Method	Method detail	Resolution	Qualifier	References
6mACE-seq	affinity-based	high		Koh, CWQ, et al. 2018. Single-nucleotide-resolution sequencing of human N6-methyldeoxyadenosine reveals strand-asymmetric clusters associated with SSBP1 on the mitochondrial genome. Nucleic Acids Research. 46(22).
DA-6mA-seq	restriction endonuclease	high	target sequences	Luo, GZ, et al. 2016. Characterization of eukaryotic DNA N(6)-methyladenine by a highly sensitive restriction enzyme-assisted sequencing. Nature Communications. 7.
SMRT	direct detection	single-base	target sequences	Flusberg, BA, et al. 2010. Direct detection of DNA methylation during single-molecule, real-time sequencing. Nature Methods. 7(6). Clark, TA, et al. 2011. Characterization of DNA methyltransferase specificities using single-molecule, real-time DNA sequencing. Nucleic Acids Research. 40(4). Murray, IA, et al. 2012. The methylomes of six bacteria. Nucleic Acids Research. 40(22).
dye-terminator Sanger sequencing	direct detection	single-base		Rao, BS, et al. 1998. Direct visualization of site-specific and strand-specific DNA methylation patterns in automated DNA sequencing data. Nucleic Acids Research. 26(10). Bart, A, et al. 2005. Direct detection of methylation in genomic DNA. Nucleic Acids Research. 33(14).
nanopore	direct detection	single-base	target sequences	Rand, AC, et al. 2017. Mapping DNA methylation with high-throughput nanopore sequencing. Nature Methods. 14(4).

Nature

Origin	Function	Functional detail	Organisms	References
natural	epigenetic mark		Arabidopsis thaliana Arthrobacter luteus Bacillus amyloliquefaciens Bacillus aneurinolyticus Bacillus caldolyticus Bacillus stearothermophilus Bombyx mori Caenorhabditis elegans Chlamydomonas reinhardtii Clostridium thermoaceticum Clostridium thermoautotrophicum Clostridium thermosaccharolyticum Danio rerio Desulfotomaculum nigrificans Drosophila melanogaster Escherichia coli Fusobacterium nucleatum Haemophilus aegyptius Haemophilus gallinarum Haemophilus haemolyticus Haemophilus influenzae Haemophilus influenzae Haemophilus parainfluenzae Klebsiella pneumoniae Methanobacterium thermoautotrophicum Methanococcus Moraxella bovis Moraxella nonliquefaciens Nocardia aerocolonigenes Proteus vulgaris Rhodopseudomonas sphaeroides Serratia marcescens Streptococcus pneumoniae Sus scrofa Thermoanaerobacter kivui Thermobacteroides acetoethylicus thermolithotrophicus Thermus aquaticus Xanthomonas campestris	Ehrlich, M, et al. 1985. DNA methylation in thermophilic bacteria: N4-methylcytosine, 5-methylcytosine, and N6-methyladenine. Nucleic Acids Research. 13(4). Ehrlich, M, et al. 1987. N4-methylcytosine as a minor base in bacterial DNA. Journal of Bacteriology. 169(3). Heyn, H, et al. 2015. An Adenine Code for DNA: A Second Life for N6-Methyladenine. Cell. 161(4). Greer, EL, et al. 2015. DNA Methylation on N6-Adenine in C elegans. Cell. 161(4). Zhang, G, et al. 2015. N6-methyladenine DNA modification in Drosophila. Cell. 161(4). Liu, J, et al. 2016. Abundant DNA 6mA methylation during early embryogenesis of zebrafish and pig. Nature Communications. 7. Liang, Z, et al. 2018. 6-Adenine Methylation in Arabidopsis thaliana. Developmental Cell. 45(3). Wang, X, et al. 2018. DNA methylation on N6-adenine in lepidopteran Bombyx mori. Biochimica Et Biophysica Acta. Gene Regulatory Mechanisms. .

Database references:

CHEBI:28871

Citations

Aik, W, et al. 2013. Structural basis for inhibition of the fat mass and obesity associated protein (FTO). Journal of Medicinal Chemistry. 56(9).
Bart, A, et al. 2005. Direct detection of methylation in genomic DNA. Nucleic Acids Research. 33(14).
Clark, TA, et al. 2011. Characterization of DNA methyltransferase specificities using single-molecule, real-time DNA sequencing. Nucleic Acids Research. 40(4).
Ehrlich, M, et al. 1987. N4-methylcytosine as a minor base in bacterial DNA. Journal of Bacteriology. 169(3).
Ehrlich, M, et al. 1985. DNA methylation in thermophilic bacteria: N4-methylcytosine, 5-methylcytosine, and N6-methyladenine. Nucleic Acids Research. 13(4).
Flusberg, BA, et al. 2010. Direct detection of DNA methylation during single-molecule, real-time sequencing. Nature Methods. 7(6).
Greer, EL, et al. 2015. DNA Methylation on N6-Adenine in C. elegans. Cell. 161(4).
Heyn, H, et al. 2015. An Adenine Code for DNA: A Second Life for N6-Methyladenine. Cell. 161(4).
Huang, S, et al. 2015. N6-methyladenine: a potential epigenetic mark in eukaryotes. Oncotarget. 6(18).
Koh, CWQ, et al. 2018. Single-nucleotide-resolution sequencing of human N6-methyldeoxyadenosine reveals strand-asymmetric clusters associated with SSBP1 on the mitochondrial genome. Nucleic Acids Research. 46(22).
Liang, Z, et al. 2018. 6-Adenine Methylation in Arabidopsis thaliana. Developmental Cell. 45(3).
Liu, J, et al. 2016. Abundant DNA 6mA methylation during early embryogenesis of zebrafish and pig. Nature Communications. 7.
Luo, GZ, et al. 2016. Characterization of eukaryotic DNA N(6)-methyladenine by a highly sensitive restriction enzyme-assisted sequencing. Nature Communications. 7.
Murray, IA, et al. 2012. The methylomes of six bacteria. Nucleic Acids Research. 40(22).
Rand, AC, et al. 2017. Mapping DNA methylation with high-throughput nanopore sequencing. Nature Methods. 14(4).
Rao, BS, et al. 1998. Direct visualization of site-specific and strand-specific DNA methylation patterns in automated DNA sequencing data. Nucleic Acids Research. 26(10).
Razin, A, et al. 1980. Methylated bases in mycoplasmal DNA. Nucleic Acids Research. 8(6).
Summerer, D, et al. 2015. N(6) -Methyladenine: A Potential Epigenetic Mark in Eukaryotic Genomes. Angewandte Chemie (International Ed. in English). 54(37).
Sun, Q, et al. 2015. N6-methyladenine functions as a potential epigenetic mark in eukaryotes. BioEssays : News and Reviews in Molecular, Cellular and Developmental Biology. 37(11).
Wang, X, et al. 2018. DNA methylation on N6-adenine in lepidopteran Bombyx mori. Biochimica Et Biophysica Acta. Gene Regulatory Mechanisms. .
Zhang, G, et al. 2015. N6-methyladenine DNA modification in Drosophila. Cell. 161(4).