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Ethyl methanesulfonate



Ethyl methanesulfonate[1]
IUPAC name 1-Methylsulfonyloxyethane
Other names Ethyl mesylate
Ethyl methanesulphonate
Identifiers
Abbreviations EMS
CAS number 62-50-0
PubChem 6113
SMILES CCOS(=O)(=O)C
InChI InChI=1/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3
Properties
Molecular formula C3H8O3S
Molar mass 124.16 g mol-1
Appearance Clear colorless liquid
Density 1.1452 at 22 °C
Melting point

<25 °C

Boiling point

213-213.5 °C

Hazards
NFPA 704
1
1
0
 
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Ethyl methanesulfonate (EMS) is a mutagenic, teratogenic, and possibly carcinogenic organic compound with formula C3H8O3S. It produces random mutations in genetic material by nucleotide substitution; specifically by guanine alkylation. This typically produces only point mutations. It can induce mutations at a rate of 5x10-4 to 5x10-2 per gene without substantial killing. The ethyl group of EMS reacts with guanine in DNA, forming the abnormal base O-6-ethylguanine. During DNA replication, DNA polymerases that catalyze the process frequently place thymine, instead of cytosine, opposite O-6-ethylguanine. Following subsequent rounds of replication, the original G:C base pair can become an A:T pair. This changes the genetic information, is often harmful to cells, and can result in disease. Many mutagens cause a wide variety of cancers in humans.

Additional recommended knowledge

EMS is often used in genetics as a mutagen. Mutations induced by EMS can then be studied in genetic screens or other assays.

Popular culture

In the 1982 movie Blade Runner, replicant Roy Batty asks Dr. Eldon Tyrell about the possibility of extending his preprogrammed lifespan by changing his genetic code with "EMS recombination". He is informed that ethyl methanesulfonate is a potent mutagen and that a test subject was "dead before he left the table."

References

  1. ^ Merck Index, 11th Edition, 3782.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Ethyl_methanesulfonate". A list of authors is available in Wikipedia.
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