m6AD – 6-methyladenine

Name
WID	m6AD
Name	6-methyladenine
Traditional name	N-methyl-9H-purin-6-amine
IUPAC name	6-map
Cross references	ChEBI: 201188, CAS: 22387-37-7, PubChem: 85399901

Classification
Type	modified_nucleobase_methylation

Structure
Empirical formula (pH 7.5)	H₇C₆N₅
SMILES (pH 7.5)	CNC1=NC=NC2=C1N=CN2
Charge (pH 7.5)	0
Is hydrophobic	False
Molecular weight (Da)	149.15
van der Waals volume (pH 7.5; Å³ molecule^‑1)	124.67
pI	7.61
logP	-0.230
logD (pH 7.5)	-0.240

Function
Reaction participant	MunI DNA restriction/modification, DNA base methylation (adenine ==> 6-methyladenine; S-Adenosyl-L-methionine) [c]: AD + AMET ⇒ AHCYS + H + m6AD DNA base methylation (adenine ==> 6-methyladenine; Methyl radical) [c]: AD + CH3 ⇒ H + m6AD EcoD DNA restriction/modification, DNA base methylation (adenine ==> 6-methyladenine; S-Adenosyl-L-methionine) [c]: AD + AMET ⇒ AHCYS + H + m6AD

Comments
Comments	majority of m6dA in bacteria is due to action of restriction-modification systems [PUB_0478]; 0.3-3% adenosine replacement in bacteria [PUB_0478];
References	Gommers-Ampt JH, Borst P. Hypermodified bases in DNA. FASEB J 9, 1034-42 (1995). WholeCell: PUB_0478, PubMed: 7649402

Metadata
Created	2012-10-01 15:07:02
Last updated	2012-10-01 15:12:20