Methanesulfonic acid methyl ester
Methyl mesylate; MMS
3D model (Jmol)
|Molar mass||110.13 g/mol|
|Density||1.3 g/mL at 25 °C|
|Boiling point||202 to 203 °C (396 to 397 °F; 475 to 476 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical reactions with DNA
MMS methylates DNA predominantly on N7-deoxyguanosine and N3-deoxyadenosine, and to a much lesser extent also methylates at other oxygen and nitrogen atoms in DNA bases, and also methylates the phosphodiester linkage. Originally, this action was believed to directly cause double-stranded DNA breaks, because homologous recombination-deficient cells are particularly vulnerable to the effects of MMS. However, it is now believed that MMS stalls replication forks, and cells that are homologous recombination-deficient have difficulty repairing the damaged replication forks.
Dimethyl sulfite, a chemical with the same molecular formula but different arrangement
- Scorecard Pollution Information Site: Methyl Methanesulfonate Scorecard.org Accessed 14 Feb 08
- Medical.Webends.com: Methyl Methanesulfonate Medical.webends.com Accessed 14 Feb 08
- Lundin C, North M, Erixon K, Walters K, Jenssen D, Goldman AS, Helleday T (2005). "Methyl methanesulfonate (MMS) produces heat-labile DNA damage but no detectable in vivo DNA double-strand breaks". Nucleic Acids Research. 33 (12): 3799–3811. doi:10.1093/nar/gki681. PMC . PMID 16009812.