Phenylmethylsulfonyl fluoride

PMSF is an irreversible serine/cysteine protease inhibitor commonly used in the preparation of cell lysates.

Phenylmethanesulfonyl fluoride is an acyl fluoride with phenylmethanesulfonyl as the acyl group. It has a role as a serine proteinase inhibitor. It derives from a phenylmethanesulfonic acid.|An enzyme inhibitor that inactivates IRC-50 arvin, subtilisin, and the fatty acid synthetase complex.

General procedure: To a stirred solution of p-tolyl disulfide (246.3 mg, 1.0 mmol) in acetonitrile (10.0 ml) and water (1.0 ml) was added Selectfluor.(TM). (2306.2 mg, 6.5 mmol) and the resulting mixture was heated under reflux for 1.5 h. The reaction was monitored by thin layer chromatography (TLC). After the disulfide and the corresponding thiosulfonate disappeared from the TLC, water (10 ml) was added and the resulting mixture was extracted with ethyl acetate (20 ml .x. 3). The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. Chromatography on silica gel gave the sulfonyl fluoride (299.0 mg, 86percent) as colorless crystals.General procedure: To a stirred solution of p-tolyl disulfide ( 1b) (246.3mg, 1.0mmol) in acetonitrile (10.0mL) and water (1.0mL), Selectfluor™ (2306mg, 6.5mmol) was added at room temperature for over 20min, and the resulting mixture was heated under reflux. The reaction was monitored via TLC. After the disulfide and the corresponding thiosulfonate disappeared from the TLC, water (10mL) was added, and the resulting mixture was extracted withethyl acetate (20mL×3). The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. Chromatography on silica gel using n-hexane/ethyl acetate as the eluent gave the sulfonyl fluoride ( 3b) (299.0mg, 86percent) as colorless crystalsIn a clean, dry 10 ml Schlenk reaction tube, Followed by the addition of benzyl sulfonyl hydrazide 46.5 mg, 1-chloromethyl-4-fluoro-1, 4-diazotized bicycles 2.2.2 octane bis (tetrafluoroborate) 123 mg, And the reaction was stirred at 60 ° C for 18 hours with 2 ml of water as the reaction solvent.After completion of the reaction, extraction was carried out by adding ethyl acetate, The upper organic phase directly spin dry with a small amount of petroleum ether and ethyl acetate (volume ratio of 30: 1) dissolved, The column was separated by a short column of silica gel to give 34.8 mg of a white solid in 80percent yield.General procedure: To a stirred solution of p-tolyl disulfide (246.3 mg, 1.0 mmol) in acetonitrile (2.0 ml) and water (0.2 ml) was added Selectfluor.(TM). (885.5 mg, 2.5 mmol) at room temperature for 20 min, and the resulting mixture was stirred. The reaction was monitored by thin layer chromatography (TLC). After the disulfide disappeared from the TLC, water (5 ml) was added and the resulting mixture was extracted with ethyl acetate (15 ml .x. 3). The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. Chromatography on silica gel gave thiosulfonate (259.3 mg, 93percent) as colorless crystals.General procedure: Representative experimental procedure to prepare thiosulfonates from disulfides General procedure: To a stirred solution of 4, 4′-dimethylphenyl thiosulfonate (2b) (278.0mg, 1.0mmol) in acetonitrile (10.0mL) and water (1.0mL), Selectfluor™ (1594mg, 4.5mmol) was added at room temperature for over 20min, and the resulting mixture was heated under reflux for 1.5h. The reaction was monitored via TLC. After the thiosulfonate disappeared from the TLC, water (10mL) was added and the resulting mixture was extracted with ethyl acetate (20mL×3). The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. Chromatography on silica gel using n-hexane/ethyl acetate as the eluent gave the sulfonyl fluoride ( 3b) (347.8mg, quant.) as colorless crystals.General procedure: To a cold (0 °C) solution of tetrabutylammonium fluoride in THF (1.0 eq, 1.0 M), a solution of the corresponding sulfonyl bromide 2 (0.5 mmol) in THF (1.6 mL), was added under an argon atmosphere. The reaction mixture was warmed to rt and after 1h, the reaction was diluted with water (30 mL) and extracted with EtOAc (x3). The combined organic extracts were dried over anh. NaEXAMPLE 19

Standard protease inhibitor in biological research; in protein purification to prevent proteolytic degradation.

Molecular Weight:174.19
XLogP3:1.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:174.01507880
Monoisotopic Mass:174.01507880
Topological Polar Surface Area:42.5
Heavy Atom Count:11
Complexity:199
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes