Ethyl methanesulfonate

Source: Wikipedia, the free encyclopedia.
Ethyl methanesulfonate[1]
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Ethyl methanesulfonate
Other names
Ethyl mesylate
Ethyl methanesulphonate
Identifiers
3D model (
JSmol
)
Abbreviations EMS
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.000.488 Edit this at Wikidata
EC Number
  • 200-536-7
KEGG
UNII
  • InChI=1S/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3 checkY
    Key: PLUBXMRUUVWRLT-UHFFFAOYSA-N checkY
  • InChI=1/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3
    Key: PLUBXMRUUVWRLT-UHFFFAOYAM
  • O=S(=O)(OCC)C
Properties
CH3SO3C2H5
Molar mass 124.16 g/mol
Appearance Clear colorless liquid
Density 1.1452 g/cm3 (22 °C)
Melting point < 25 °C
Boiling point 85–86 °C (185–187 °F; 358–359 K) /10 mmHg(lit)
Vapor pressure 0.044 kPa @ 25˚C[2]
Hazards
GHS labelling:[3]
GHS07: Exclamation markGHS08: Health hazard
Danger
H302, H340, H351
P203, P264, P270, P280, P301+P317, P318, P330, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Ethyl methanesulfonate (EMS) is an

alkylating agent. EMS is the most commonly used chemical mutagen in experimental genetics.[4][5] Mutations induced by EMS exposure can then be studied in genetic screens
or other assays.

Use in biological research

EMS produces random

transitions induced by guanine alkylation. EMS typically produces only point mutations
. Due to its potency and well understood mutational spectrum,

EMS can induce mutations at a rate of 5x10−4 to 5x10−2 per gene without substantial killing. A 5x10−4 per gene mutation rate observed in a typical EMS mutagenesis experiment of the model organism

heterozygous non-functional mutated allele may be rescued by the still wildtype allele provided by the other gamete.[6]

Mechanism of mutagenesis

The

transition mutation). This changes the genetic information, is often harmful to cells, and can result in disease. RNA polymerase can also place uridine (RNA analog of thymine) opposite an O6-ethylguanine lesion.[7]

Repair of mutagenic lesion

O6-ethylguanine can be repaired

O-6-methylguanine-DNA methyltransferase repair protein.[8] The in vivo half-life of O6-ethylguanine was reported to be about 9 days in mouse brain, while it was about 1 day in mouse liver.[9]

Induction of recombination

EMS induces mitotic recombination in Saccharomyces cerevisiae.[10] It was suggested that EMS damage to DNA may result in a repair process leading to genetic exchange.[10]

Bacteriophage T4 mutants defective in any one of six genes known to be required for genetic recombination were found to be more sensitive to inactivation by EMS than wild type bacteriophage.[11] This finding suggests that a recombination process catalyzed by the proteins specified by these six genes is employed in repairing EMS lethal lesions in DNA.[11]

Stability

Generally speaking EMS is unstable in water. It hydrolyzes to ethanol and methanesulfonic acid. At neutral to acidic pH at room temperature, it has a fairly long

NaOH and 20% w/v sodium thiosulfate "inactivating solution", for at least six half-lives (>24 hours).[6] The half-life of EMS in 1M NaOH is 6 hours at room temperature, while in a 10% w/v sodium thiosulfate solution it has a half-life of 1.4 hours.[13]

Safety

EMS is

teratogenic, and carcinogenic
.

See also

References

  1. ^ Merck Index, 11th Edition, 3782.
  2. ^ "Ethyl Methanesulfonate" (PDF). Report on Carcinogens, Fourteenth Edition. NIEHS. Retrieved 18 June 2021.
  3. ^ "Ethyl methanesulfonate". pubchem.ncbi.nlm.nih.gov.
  4. PMID 24449699
    . Retrieved 18 June 2021.
  5. PMID 6390190
    .
  6. ^
    ISSN 0091-679X
    .
  7. PMID 4706005
    .
  8. PMID 10767620
    .
  9. PMID 4522778
    .
  10. ^
    S2CID 1982778
    .
  11. ^
    S2CID 30597383
    .
  12. S2CID 12359460
    .
  13. ^
    OCLC 51445955
    .
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