Biotransformations of aryl alkyl sulfides by whole cells of white-rot Basidiomycetes

Ricci, Luís C.; Comasseto, J. V.; Andrade, Leandro H.; Capelari, Marina; Cass, Quézia B.; Porto, André Luiz Meleiro

doi:10.1016/j.enzmictec.2005.01.021

Cited by 36 publications

(16 citation statements)

References 28 publications

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“…213 Sugimoto reported that kinetic resolution took place when oxidising racemic sulfoxide with hydrogen peroxide in the presence of BSA. 188 The highest enantioselectivity was observed in the kinetic resolution of tert-butyl phenyl sulfoxide 166, which was isolated with 33% ee after the kinetic resolution experiment. Using a combination of both asymmetric sulfide oxidation and kinetic resolution, Sugimoto obtained phenyl iso-propyl sulfoxide 162 in 93% ee.…”

Section: Biological Methodsmentioning

confidence: 94%

“…The oxidation of phenyl propyl sulfide 170 produced the (S)-sulfoxide in enantiopure form. 188 Olivo et al reported a highly enantioselective oxidation of benzhydrylsulfanyl acetic acid to the corresponding (S)-sulfinyl carboxylic acid using the fungus Beauveria bassiana. The sulfoxide 172 was produced in excellent yield (89%) and enantioselectivity (99%) (Scheme 69).…”

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confidence: 99%

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Synthesis of enantioenriched sulfoxides

O’Mahony¹,

Kelly²,

Lawrence³

et al. 2011

Arkivoc

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This review discusses strategies for the asymmetric synthesis of sulfoxides, compounds with many applications in stereoselective synthesis and in some cases with pharmaceutical application. The review describes asymmetric oxidation, including metal catalyzed and nonmetal and biological oxidation processes, in addition to synthetic approaches via nucleophilic substitution of appropriately substituted precursors. Kinetic resolution in oxidation of sulfoxides to the analogous sulfones is also discussed; in certain instances, access to enantioenriched sulfoxides can be achieved via a combination of asymmetric sulfide oxidation and complementary kinetic resolution in sulfoxide oxidation.

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Section: Biological Methodsmentioning

confidence: 94%

mentioning

confidence: 99%

Synthesis of enantioenriched sulfoxides

O’Mahony¹,

Kelly²,

Lawrence³

et al. 2011

Arkivoc

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“…By contrast, asymmetric sulfoxidations catalyzed by whole-cell systems (e.g., fungi and bacteria) are much cheaper and more convenient, avoiding the involvement of expensive cofactors (NADH/NADPH). Although a few microorganisms have so far been successfully used for such a biocatalytic sulfoxidation, the most frequently used cultures for this purpose were fungi (12,21,22). For the bacteria, there have been only a few brief reports regarding the oxidation of sulfides with whole cells (2,15), but the results were unsatisfactory because of low enantioselectivity or poor substrate tolerance.…”

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confidence: 99%

Isolation of Rhodococcus sp. Strain ECU0066, a New Sulfide Monooxygenase-Producing Strain for Asymmetric Sulfoxidation

Zhang

et al. 2009

Appl Environ Microbiol

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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.Because of the high configurational stability of the sulfinyl group as well as their synthetic versatility, chiral sulfoxides are powerful stereodirecting groups (18), valuable asymmetric starting materials (19), and chiral auxiliaries (7). The value of chiral sulfoxide functionality is further illustrated by their diverse biological activities and pharmaceutical uses (17). In many cases, only one enantiomer of a sulfur-containing drug exhibits the desired biological activity (10); therefore, it is necessary and important to prepare enantiopure sulfoxides.The asymmetric oxidation of a prochiral sulfide is undoubtedly a more direct and economical method for the synthesis of enantiomerically pure sulfoxides than the kinetic resolution of racemic sulfoxides. Asymmetric sulfoxidations mediated by either metal catalysts or isolated enzymes have received considerable attention over the past several years (1,9,14,20,24). However, the transformations with metal catalysts or isolated enzymes (such as peroxidases, haloperoxidases, and monooxygenases) are tedious and expensive, which are major disadvantages for preparative applications. And only very few of the enzymes used for sulfoxidation, such as the cyclohexanone monooxygenase from Acinetobacter NCBI 9871, have been isolated and characterized (8). By contrast, asymmetric sulfoxidations catalyzed by whole-cell systems (e.g., fungi and bacteria) are much cheaper and more convenient, avoiding the involvement of expensive cofactors (NADH/NADPH). Although a few microorganisms have so far been successfully used for such a biocatalytic sulfoxidation, the most frequently used cultures for this purpose were fungi (12,21,22). For the bacteria, there have been only a few brief reports regarding the oxidation of sulfides with whole cells (2, 15), but the results were unsatisfactory because of low enantioselectivity or poor substrate tolerance. Therefore, we decided to screen for new bacterial strains with higher enzyme activity and better enantioselectivity for asymmetric oxidation of sulfides.In this article, we report the catalytic performance of the newly isolated bacterium Rhodococcus sp. strain ECU0066 for asymmetric oxidation of sulfides. This bacterium displayed pretty high activity and satisfactory enantioselectivity for most of the sulfides examined, indicating that this bacterium is very ...

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“…Enantiomerically pure sulfoxides are useful building blocks for the synthesis of pharmaceuticals and biologically active compounds [1]. As natural products, they occur in a variety of functionalized amino acids possessing various biological activities.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric oxidation of organic sulfides by the filamentous fungi Botrytis cinerea, Eutypa lata and Trichoderma viride

Pinedo-Rivilla

Aleu

Collado

2007

Journal of Molecular Catalysis B: Enzymatic

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The biotransformations of a series of substituted sulfides were carried out with the filamentous fungi Botrytis cinerea, Eutypa lata and Trichoderma viride. Several products underwent microbial oxidation of sulfide to sulfoxide with medium to high enantiomeric purity. With regard to sulfoxide enantioselectivity, the (R)-enantiomer was favoured in biotransformations by T. viride and E. lata while the (S)-enantiomer was favoured in those by B. cinerea. A minor amount of sulfone product was also obtained.

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Biotransformations of aryl alkyl sulfides by whole cells of white-rot Basidiomycetes

Cited by 36 publications

References 28 publications

Synthesis of enantioenriched sulfoxides

Synthesis of enantioenriched sulfoxides

Isolation of Rhodococcus sp. Strain ECU0066, a New Sulfide Monooxygenase-Producing Strain for Asymmetric Sulfoxidation

Enantiomeric oxidation of organic sulfides by the filamentous fungi Botrytis cinerea, Eutypa lata and Trichoderma viride

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