MMSO4 – dimethyl sulfate

Name
WID	MMSO4
Name	dimethyl sulfate
Traditional name	dimethylsulfate
IUPAC name	dimethyl sulfate
Cross references	ChEBI: 371544, PubChem: 85563059

Classification
Type	alkylating_agent_methylation

Structure
Empirical formula (pH 7.5)	H₆C₂O₄S₁
SMILES (pH 7.5)	COS(=O)(=O)OC
Charge (pH 7.5)	0
Is hydrophobic	False
Molecular weight (Da)	126.13
van der Waals volume (pH 7.5; Å³ molecule^‑1)	99.32
logP	-0.0900
logD (pH 7.5)	-0.0900

Function
Reaction participant	DNA base methylation (cytosine ==> 3-methylcytosine; dimethyl sulfate) [c]: CSN + MMSO4 ⇒ m3CSN + MSO4 DNA base methylation (adenine ==> 1-methyladenine; dimethyl sulfate) [c]: AD + H + MMSO4 ⇒ m1AD + MSO4 DNA base methylation (adenine ==> 3-methyladenine; dimethyl sulfate) [c]: AD + MMSO4 ⇒ m3AD + MSO4 DNA base methylation (guanine ==> 7-methylguanine; dimethyl sulfate) [c]: GN + H + MMSO4 ⇒ m7GN + MSO4 DNA base methylation (adenine ==> 7-methyladenine; dimethyl sulfate) [c]: AD + MMSO4 ⇒ m7AD + MSO4 ... 2 more DNA base methylation (guanine ==> 6'-O-methylguanine; dimethyl sulfate) [c]: GN + MMSO4 ⇒ MSO4 + O6mGN DNA base methylation (guanine ==> 3-methylguanine; dimethyl sulfate) [c]: GN + MMSO4 ⇒ m3GN + MSO4

Comments
Comments	SN2 DNA methylating agent [PUB_0465]
References	Sedgwick B. Repairing DNA-methylation damage. Nat Rev Mol Cell Biol 5, 148-57 (2004). WholeCell: PUB_0465, PubMed: 15040447

Metadata
Created	2012-10-01 15:07:03
Last updated	2012-10-01 15:12:22