Chemical Properties
White to cream solid
Uses
Phenylmethylsulfonyl fluoride is used as a Protease inhibitor such as Chymotrypsin, Trypsin and Thrombin as well as Acetylcholineesterase.
Uses
PMSF is an irreversible serine/cysteine protease inhibitor
Uses
Standard protease inhibitor in biological research; in protein purification to prevent proteolytic degradation.
Definition
ChEBI: An acyl fluoride with phenylmethanesulfonyl as the acyl group.
General Description
In biochemistry, Phenylmethylsulfonyl fluoride (PMSF) is a serine protease inhibitor commonly used in preparation of cell lysates. It is rapidly degraded in water and stock solutions are usually made up in anhydrous ethanol, isopropanol, corn oil, or DMSO (Dimethyl sulfoxide).
Hazard
Extremely corrosive and destructive to tissues. May cause irreversible eye damage. PMSF hydrolyzes upon exposure to water/moisture, liberating a toxic and corrosive gas (hydrogen flouride) that in contact with metal surfaces can generate flammable and/or explosive hydrogen gas.
Biological Activity
pmsf (phenylmethanesulfonyl fluoride) is an irreversible inhibitor of serine proteinases, which is associated with the development of the delayed organophosphorus neuropathy. it has a role in a lot of cellular repair and regeneration processes in many kinds of tissues. pmsf is a long acting neuropathy target esterase (nte) inhibitor. nte is a protection was related to inhibition of the putative target of organophosphate-induced delayed polyneuropathy (opidp). pmsf can increase nte inhibition to more than 90%. pmsf also acts as an active site directed reagent for γ-glutamyl transpeptidase.thomas baker, herbert e. lowndes, martin k. johnson, irene c. sandborg. the effects of phenylmethanesulfonyl fluoride on delayed organophosphorus neuropathy. archives of toxicology. 1980; 46(3-4): 305 – 311.marcello lotti, stefano caroldi, eugenio capodicasa, angelo moretto. promotion of organophosphate-induced delayed polyneuropathy by phenylmethanesulfonyl fluoride. toxicology and applied pharmacology. 1991; 108(2): 234 – 241.masayasu inoue, seikoh horiuchi, yoshimasa morino. inactivation of γ-glutamyl transpeptidase by phenylmethanesulfonyl fluoride, a specific inactivator of serine enzymes. biochemical and biophysical research communications. 1978; 82(4): 1183 – 1188.
Biochem/physiol Actions
Phenylmethanesulfonyl fluoride has the ability to enhance the stability of plasma lipidome in lipidomic and metabolomic analysis. This serine protease inhibitor reduces the naloxone-precipitated withdrawal jumping behavior in morphine-dependent mice.
Synthesis
General procedure for the synthesis of phenylmethylsulfonyl fluoride from dibenzyl disulfide: Selectfluor? (2306.2 mg, 6.5 mmol) was added to a stirred mixed solution of dibenzyl disulfide (246.3 mg, 1.0 mmol) in acetonitrile (10.0 mL) and water (1.0 mL). The reaction mixture was heated under reflux conditions for 1.5 h and the progress of the reaction was monitored by thin layer chromatography (TLC). After the dibenzyl disulfide and the corresponding thiosulfonate disappeared on TLC, water (10 mL) was added to the reaction mixture and extracted with ethyl acetate (20 mL × 3). The organic phases were combined, washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Finally, it was purified by silica gel column chromatography to obtain phenylmethylsulfonyl fluoride (299.0 mg, 86% yield) in colorless crystal form.
Purification Methods
Purify PMSF by recrystallisation from *C6H6, pet ether or CHCl3/pet ether. [Davies & Dick J Chem Soc 483 1932, cf Tullock & Coffman J Org Chem 23 2016 1960.] It is a general protease inhibitor (specific for trypsin and chymotrypsin) and is a good substitute for diisopropylphosphoro floridate [Fahrney & Gould J Am Chem Soc 85 997 1963]. [Beilstein 11 III 331.]
References
[1] Tetrahedron Letters, 2011, vol. 52, # 24, p. 3086 - 3089
[2] Tetrahedron, 2014, vol. 70, # 14, p. 2464 - 2471
[3] Tetrahedron, 2014, vol. 70, # 14, p. 2464 - 2471
