329-98-6 Usage
Description
Phenylmethylsulfonyl fluoride (PMSF) is an acyl fluoride with phenylmethanesulfonyl as the acyl group. It is a potent and irreversible serine/cysteine protease inhibitor, derived from phenylmethanesulfonic acid. PMSF is a white to cream solid and is widely used in biological research and protein purification to prevent proteolytic degradation.
Uses
1. Used in Biological Research:
Phenylmethylsulfonyl fluoride is used as a protease inhibitor for various serine/cysteine proteases such as chymotrypsin, trypsin, and thrombin, as well as acetylcholineesterase. It plays a crucial role in maintaining the integrity of proteins during research, ensuring accurate results and minimizing the risk of proteolytic degradation.
2. Used in Protein Purification:
PMSF is a standard protease inhibitor in protein purification processes. It helps prevent the degradation of proteins by inhibiting the activity of proteases, ensuring that the purified proteins maintain their structural and functional integrity.
3. Used in Pharmaceutical Industry:
Phenylmethylsulfonyl fluoride is used as a protease inhibitor in the development of drugs targeting various diseases. Its ability to inhibit proteases makes it a valuable tool in the design and synthesis of therapeutic agents.
4. Used in Diagnostics:
PMSF can be employed in the development of diagnostic tools and assays that require the inhibition of proteases to prevent interference with the detection of specific biomarkers or other molecules of interest.
5. Used in Food Industry:
In the food industry, PMSF can be used as a preservative to inhibit the activity of proteases that may cause spoilage or degradation of food products, thereby extending their shelf life and maintaining their quality.
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.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 329-98-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,2 and 9 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 329-98:
(5*3)+(4*2)+(3*9)+(2*9)+(1*8)=76
76 % 10 = 6
So 329-98-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H7FO2S/c1-6-4-2-3-5-7(6)11(8,9)10/h2-5H,1H3
329-98-6Relevant articles and documents
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Davies,Dick
, p. 483,485 (1932)
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Method for preparing alkyl sulfonyl fluoride
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Paragraph 0084-0087, (2021/11/27)
The invention relates to a method for preparing alkyl sulfonyl fluoride, wherein the reducing active ester converted from alkyl carboxylic acid is a raw material, the sulfur dioxide substitution reagent is a sulfur dioxide source, and the electrophilic fluorinating reagent is a fluorine source. Compared with the prior art, the synthesis method is simple, has the selectivity of in-situ introduction of the sulfonyl fluoride group and high yield, and is easy to implement large-scale production.
Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride
Laudadio, Gabriele,Bartolomeu, Aloisio De A.,Verwijlen, Lucas M. H. M.,Cao, Yiran,De Oliveira, Kleber T.,No?l, Timothy
supporting information, p. 11832 - 11836 (2019/08/26)
Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based "click chemistry" is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups is of great interest. Herein, we report a mild and environmentally benign electrochemical approach to prepare sulfonyl fluorides using thiols or disulfides, as widely available starting materials, in combination with KF, as an inexpensive, abundant and safe fluoride source. No additional oxidants nor additional catalysts are required and, due to mild reaction conditions, the reaction displays a broad substrate scope, including a variety of alkyl, benzyl, aryl and heteroaryl thiols or disulfides.
Sulfur(VI) fluoride compounds and methods for the preparation thereof
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Page/Page column 19; 20; 36; 45; 47, (2018/11/23)
This application describes a compound represented by Formula (I): (I) wherein: Y is a biologically active organic core group comprising one or more of an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group, to which Z is covalently bonded; n is 1, 2, 3, 4 or 5; m is 1 or 2; Z is O, NR, or N; X1 is a covalent bond or —CH2CH2—, X2 is O or NR; and R comprises H or a substituted or unsubstituted group selected from an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group. Methods of preparing the compounds, methods of using the compounds, and pharmaceutical compositions comprising the compounds are described as well.