A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase

Alvarez, Ricardo G.; Hunter, Iain S.; Suckling, Colin J.; Thomas, Michael J.; Vitinius, Ute

doi:10.1016/s0040-4020(01)00837-7

Cited by 29 publications

(11 citation statements)

References 20 publications

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“…3-Alkylbenzo[b]furans 79 were oxidized by chloroperoxidase from Caldariomyces fumago to their trans-2,3-diols as major products 81 and 82 in addition to methylacetate derivative 80 [32] (Scheme 24).…”

Section: Oxidationmentioning

confidence: 99%

Reactivity of Benzofuran Derivatives

Abu‐Hashem

Hussein²,

Aly³

et al. 2014

Synthetic Communications

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Section: Oxidationmentioning

confidence: 99%

Reactivity of Benzofuran Derivatives

Abu‐Hashem

Hussein²,

Aly³

et al. 2014

Synthetic Communications

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“…The oxidation of the indole derivatives 39 -41 by CPO from Caldariomyces fumago has been investigated. Under conditions in which inactivi-tation of CPO was minimised by the presence of chloride and hydrogen peroxide [46], the oxidation products of N-unsubstituted indoles tautomerised to give the corresponding lactam. 3-alkyl benzofurans 42 -45 gave 2,3-diols 46 and 47 as initial products.…”

Section: Oxidation Reactions Catalyzed By Chloro-and Bromoperoxidasesmentioning

confidence: 99%

“…3-alkyl benzofurans 42 -45 gave 2,3-diols 46 and 47 as initial products. The diols (predominantly trans) formed from the benzofurans were sufficiently stable for isolation [46]. Under conditions where catalase activity was high, the predominant products from benzofurans were heterocyclic ring cleaved compounds such as the ketoformate 44 (Scheme 8).…”

Section: Oxidation Reactions Catalyzed By Chloro-and Bromoperoxidasesmentioning

confidence: 99%

“…In the last decade peroxidases, notably CPO from Caldariomyces fumago, have been shown to catalyze a wide variety of synthetically useful (enantioselective) oxygen transfer reactions with H 2 O 2 [27,54,77,94], e.g., asymmetric epoxidation of olefins [30,42,59], benzylic, propargylic, and allylic hydroxylation [26,31], asymmetric sulfoxidation [4,61,74,77], and oxidation of indoles to the corresponding 2oxindoles [44][45][46]. However, a major shortcoming of all heme-dependent peroxidases, such as CPO, is their low operational stability [77], resulting from facile oxidative degradation of the porphyrin ring.…”

Section: Distribution Of Haloperoxidases In Naturementioning

confidence: 99%

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The Use Haloperoxidases in Organic Synthesis: Selected Reactions of Oxidation, Epoxydation and Sulfoxidation

Dembitsky

Srebnik

2017

Eurasian Chem. Tech. J.

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<p>Haloperoxidases are ubiquitous metalloenzymes that catalyse a variety of enantioselective oxygen-transfer reactions with hydrogen peroxide or alkylperoxides. Haloperoxidases are enzymes which catalyze the reaction of oxidation, epoxidation and sulfoxidation by hydrogen peroxide. These enzymes usually contain the FeHeme moiety or vanadium as an essential constituent at their active site, however, a few haloperoxidases which lack a metal cofactor are known. This review will examine the reactivity of the different haloperoxidases, particularly the mechanism of oxidation by hydrogen peroxide, and the mechanism of oxidation and sulfoxidation, including the newly reported regioselectivity and enantioselectivity of the haloperoxidases. The structure of chloroperoxidase, the vanadium active site and the role of critical amino acid side chains for catalysis and functional biomimetic systems, with specific relevance to the mechanism of the haloperoxidase enzymes. Advances have recently been made in using them to prepare, under controlled conditions, chiral organic molecules that are valuable for the synthesis of a wide range of useful compounds. The application of biocatalytic methods in asymmetric organic synthesis is of great interest as an alternative to chemical procedures employing chiral auxiliaries. Asymmetric oxidation of prochiral sulfides to yield optically active sulfoxides has been performed by many different techniques yielding varying enantiomeric excess values. Oxygenated metabolites are compounds that are commonly found in nature and they are produced by many different organisms. The oxygen atom is incorporated into organic compounds by enzyme-catalyzed reactions with oxygen ions as the oxygen source. For over 40 years haloperoxidases were thought to be responsible for the incorporation of mainly halogen atoms into organic molecules. However, haloperoxidases lack substrate specificity and regioselectivity, and the connection of haloperoxidases with the in vivo formation of oxygenated as well as halometabolites has been demonstrated. Recently, molecular genetic investigations showed that, at least in bacteria, fungi, and other organisms a different class of halogenases is involved in halo- and oxygenated metabolite formation. These halogenases were found to require FADH2, which can be produced from FAD and NADH by unspecific flavin reductases. The FADH<sub>2</sub>-dependent halogenases and haloperoxidases show substrate specificity and regioselectivity, and their genes have been detected in many halometabolite-producing organisms, suggesting that this type of halogenating enzymes constitutes the major source for halo- and oxygenated metabolite formation in bacteria and also in other organisms. Distribution of haloperoxidases in nature also is demonstrated in this brief review.</p>

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“…[44] Efficient hydroxylation of organic substrates has also been achieved with this peroxidase. Chloroperoxidase is able to catalyze the hydroxylation of 1,2-dihydronaphthalene with t-butyl hydroperoxide as oxidant [45], the hydroxylation of the furan ring with hydrogen peroxide as an O2 donor [46]. All of these are halide-dependent reactions and require the participation of halide ions.…”

Section: Reactions Catalyzed By Chloroperoxidasementioning

confidence: 99%

Enzyme Catalyzed and Ultrasound Assisted Transformation of Selected Pollutants

Tan¹

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A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase

Cited by 29 publications

References 20 publications

Reactivity of Benzofuran Derivatives

Reactivity of Benzofuran Derivatives

The Use Haloperoxidases in Organic Synthesis: Selected Reactions of Oxidation, Epoxydation and Sulfoxidation

Enzyme Catalyzed and Ultrasound Assisted Transformation of Selected Pollutants

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