Dioxygenase-catalysed sulfoxidation of bicyclic alkylaryl sulfides and chemoenzymatic synthesis of acyclic disulfoxides (original) (raw)
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2019
A large variety of organosulfur compounds have been shown to having diverse biological effects such as anti-oxidant effects, anti-inflammatory properties, inhibition of platelet aggregation, reduction of systolic blood pressure, and reduction of cholesterol. Among these, sulfoxides and sulfones show wide and significant applications as commodity chemical in various fields of chemistry. Therefore, synthesis of sulfoxides as well as sulfones has remained a point of attraction for synthetic organic chemists. Among array of methods used to synthesize the sulfoxides or sulfones, oxidation of sulfide is the most convenient way. This review precises chemoselective methods for the synthesis of the sulfoxides as well as sulfones focusing on oxidative protocols. This review will aid researchers to explore and utilise the mentioned protocols for different organic transformations.
Catalysts, 2017
A recently discovered, moderately thermostable Baeyer-Villiger monooxygenase, polycyclic ketone monooxygenase (PockeMO), from Thermothelomyces thermophila has been employed as a biocatalyst in a set of asymmetric sulfoxidations. The enzyme was able to catalyze the oxidation of various alkyl aryl sulfides with good selectivities and moderate to high activities. The biocatalytic performance was able to be further increased by optimizing some reaction parameters, such as the addition of 10% v v −1 of water miscible solvents or toluene, or by performing the conversion at a relatively high temperature (45 • C). PockeMO was found to display an optimum activity at sulfide concentrations of 50 mM, while it can also function at 200 mM. Taken together, the data show that PockeMO can be used as robust biocatalyst for the synthesis of optically active sulfoxides.
Regioselective aerobic oxidation of bis-sulfides into monosulfoxides
Journal of Molecular Catalysis A: Chemical, 2000
Ž . 1 The cobalt II acetylacetonateraldehyde-promoted aerobic oxidation of three bis-sulfides of general formula R -SCH CH S-R 2 , where R 1 is a heterocycle and R 2 is p-tolyl, provides a method to functionalise selectively the sulfur atom 2 2 bonded to the p-tolyl moiety leading to the corresponding monosulfoxides. The same chemoselectivity and little Ž . Ž . 3 diastereoisomeric excess 10% was achieved by submitting to oxidative conditions the chiral bis-sulfide S -R -
Applied and Environmental Microbiology, 2009
A new and efficient sulfide monooxygenase-producing strain, ECU0066, was isolated and identified as a Rhodococcus sp. that could transform phenylmethyl sulfide (PMS) to (S)-sulfoxide with 99% enantiomeric excess via two steps of enantioselective oxidations. Its enzyme activity could be effectively induced by adding PMS or phenylmethyl sulfoxide (PMSO) directly to a rich medium at the early log phase (6 h) of fermentation, resulting in over 10-times-higher production of the enzyme. This bacterial strain also displayed fairly good activity and enantioselectivity toward seven other sulfides, indicating a good potential for practical application in asymmetric synthesis of chiral sulfoxides.
Asymmetric oxidation of sulfides by cyclohexanone monooxygenase
Tetrahedron-asymmetry, 1993
CycIohexanone monooxygenase catalyzes the asymmetric oxidazion of numerous alkyl tnyl sulildes with the alkyl chain functionalyzed with Cl, CN, vinyl or hydroxy groups. Sulfoxides with enantiorneric excesses up to 99% were obtained. The structure of the sulfide markedly influenced enzyme enantioselectivity.
Biocatalytic Oxidation of Sulfides to Sulfones
Oriental Journal Of Chemistry, 2021
This paper describes a method for the biocatalytic oxidation of sulfides. During the screening of microorganisms using pure cultures of Bacteria and Fungi for the oxidation of sulfides, it was observed that a number of strains of microorganisms, were able to oxidize various sulfides (1-4), but the desired sulfoxide was either not obtained or obtained only as a minor product. A close observation of the reaction showed complete oxidation and thus sulfone (5-8) formation had occurred in these cases.Sulfones are used to stabilize intermediates like α-radicals, α-anionsetc. and also used as cationic synthons in many known reactions.This prompted us to explore the sulfone synthesis by biocatalytic route.Approximately 20% of the strains tested (400 bacterial and 200 fungal) showed the formation of sulfone with conversion rate varying from 3 to 100% based on TLC analysis. There were two strains of fungi, Aspergillus ochraceus MTCC 5245 and Penicillium Funiculosum MTCC 5246 which showed exce...