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ChemicalBook CAS DataBase List DIBENZOTHIOPHENE SULFONE
1016-05-3

DIBENZOTHIOPHENE SULFONE synthesis

11synthesis methods
-

Yield:1013-23-6 86% ,1016-05-3 7.2%

Reaction Conditions:

with peroxygenase;dihydrogen peroxide in acetonitrile; pH=5 at 20; for 0.416667 h;Enzymatic reaction;Concentration;

Steps:

6 Example 6 Oxidation of Dibenzothiophene
Oxidations of 1 mM dibenzothiophene with 1 mM H2O2 were carried out with 30% acetonitrile and 5 mM acetate (pH 3-5), phosphate (pH 6-7) or borate buffer (pH 8-8.5) at specified pH values using 0.01 mg/mL of purified peroxygenase (mature peroxygenase encoded by SEQ ID NO: 1) in a total reaction volume of 1 mL. Reactions were performed at room temperature for 25 minutes and samples were then inactivated with 50 μL of 50% (w/v) trichloroacetic acid. (0265) Samples were analyzed on an Agilent 1200 HPLC system equipped with a Diode Array Detector (Agilent, Santa Clara Calif., USA) and separated on a Gemini C6-Phenyl (110 , 2×150 mm, 3 μm) column from Phenomenex (Torrance Calif., USA) thermostated at 40° C. Two mobile phases were used: (A) 0.1% formic acid, and (B) 0.1% formic acid in acetonitrile. (0266) Separations were run using stepwise gradient starting with 30% B held for 0.5 min, then increasing to 80% B within 14.5 min and being maintained at 80% for 3 min with a constant flow rate of 0.4 mL/min. (0267) Dibenzothiophene and its oxidation product dibenzothiophene sulfone was identified and quantified by external calibration using authentic standards, based on their retention times, UV absorbtion spectra (230 nm and 260 nm). Dibenzothiophene oxide standard was not commercially available the quantification of this compound was done using dibenzothiophene sulfone calibration curve. (0268) The peroxygenase oxidised dibenzothiophene yielding two products dibenzothiophene oxide and dibenzothiophene sulfone. TABLE 5 Comparison of dibenzothiophene oxide (DBT-SO) and dibenzothiophene sulfone (DBT-SO2) yields calculated at various pH. (30% ACN; reaction time 1 min). pH DBT-SO (%) DBT-SO2 (%) 3.0 65.9 0.0 4.0 66.2 0.0 5.0 81.3 0.4 6.0 87.9 0.8 6.5 87.1 0.7 7.0 83.4 0.8 8.0 85.6 0.5 8.5 80.5 0.0 [table-us-00007-en] TABLE 6 Comparison of dibenzothiophene oxide (DBT-SO) and dibenzothiophene sulfone (DBT-SO2) yields calculated at various acetonitrile (ACN) concentrations (pH5.0; reaction time25 min). ACN DBT-SO DBT-SO2 (%) (%) (%) 30 72.0 12.5 40 86.0 7.2 50 89.6 1.4 60 64.1 0.8 70 14.8 0.0 80 2.1 0.0

References:

Novozymes A/S;Landvik, Sara;Oestergaard, Lars H.;Kalum, Lisbeth US9382559, 2016, B2 Location in patent:Page/Page column 33

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