m6dA – 6-methyl-2'-deoxyadenosine

Name
WID	m6dA
Name	6-methyl-2'-deoxyadenosine
Traditional name	2-(hydroxymethyl)-5-[6-(methylamino)-9H-purin-9-yl]oxolan-3-ol
IUPAC name	2-(hydroxymethyl)-5-[6-(methylamino)purin-9-yl]oxolan-3-ol

Classification
Type	modified_deoxyribonucleoside_methylation

Structure
Empirical formula (pH 7.5)	H₁₅C₁₁N₅O₃
SMILES (pH 7.5)	CNC1=NC=NC2=C1N=CN2C1CC(O)C(CO)O1
Charge (pH 7.5)	0
Is hydrophobic	False
Molecular weight (Da)	265.27
van der Waals volume (pH 7.5; Å³ molecule^‑1)	224.82
pI	9.45
logP	-0.890
logD (pH 7.5)	-0.890

Function
Reaction participant	6-methyl-2'-deoxyadenosine transport m6dA[e] ⇔ m6dA[c] 5'-nucleotidase (6-methyl-2'-deoxyadenosine monophosphate) [c]: H2O + m6dAMP ⇒ m6dA + PI

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