Chloroperoxidase from Caldariomyces fumago is active in the presence of an ionic liquid as co-solvent

Sanfilippo, Claudia; D’Antona, Nicola; Nicolosi, Giovanni

doi:10.1007/s10529-004-5087-6

Cited by 65 publications

(33 citation statements)

References 16 publications

(5 reference statements)

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“…[20] The use of tert-butylhydroperoxide (TBHP) in the place of H 2 O 2 has proven successful in some cases. [21] In other strategies, polymers [22] and antioxidants [23] were added, or co-solvents such as an ionic liquid [24,25] or ternary systems [26] were employed. Immobilization of haloperoxidases on solid supports did increase the stability of the enzyme and facilitated its recovery.…”

Section: Biological Halogenation and Biomimeticsmentioning

confidence: 99%

Oxidative Halogenation with “Green” Oxidants: Oxygen and Hydrogen Peroxide

2009

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It is difficult to imagine organic chemistry without organo-halogen compounds and the molecular halogens needed for their preparation. The halogens have very different reactivity, with iodine usually requiring some form of activation, while others are reactive and hazardous chemicals. To avoid their use, various modified reagents have been discovered (N-bromo- and N-chlorosuccinimide, Selectfluor..), but halogens are used to prepare these reagents and when they are used the atom economy is poor. A better approach, which is based on biomimetric research on oxidative halogenation in nature, consists of generating the halogenating reagent in situ under acidic conditions from a halide salt. The result of such a reaction has been halogenation with 100 % halogen atom economy. Suitable oxidants for the oxidation of halides are hydrogen peroxide and oxygen.

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Section: Biological Halogenation and Biomimeticsmentioning

confidence: 99%

Oxidative Halogenation with “Green” Oxidants: Oxygen and Hydrogen Peroxide

2009

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“…Aromatic rings, however, are not susceptible to oxygen transfer by CPO. Merely cyclic dienes, such as 1,2-dihydronyphthalene or indene, can be epoxidized by CPO and subsequently undergo spontaneous transformation to the respective oxides or dihydrodiols [190,191]. Furthermore, CPO catalyzes benzylic hydroxylation, e.g., of p-xylene or toluene [192,193].…”

mentioning

confidence: 99%

Enzymatic hydroxylation of aromatic compounds

Ullrich

Hofrichter

2007

Cell. Mol. Life Sci.

299

182

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Selective hydroxylation of aromatic compounds is among the most challenging chemical reactions in synthetic chemistry and has gained steadily increasing attention during recent years, particularly because of the use of hydroxylated aromatics as precursors for pharmaceuticals. Biocatalytic oxygen transfer by isolated enzymes or whole microbial cells is an elegant and efficient way to achieve selective hydroxylation. This review gives an overview of the different enzymes and mechanisms used to introduce oxygen atoms into aromatic molecules using either dioxygen (O(2)) or hydrogen peroxide (H(2)O(2)) as oxygen donors or indirect pathways via free radical intermediates. In this context, the article deals with Rieske-type and alpha-keto acid-dependent dioxygenases, as well as different non-heme monooxygenases (di-iron, pterin, and flavin enzymes), tyrosinase, laccase, and hydroxyl radical generating systems. The main emphasis is on the heme-containing enzymes, cytochrome P450 monooxygenases and peroxidases, including novel extracellular heme-thiolate haloperoxidases (peroxygenases), which are functional hybrids of both types of heme-biocatalysts.

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“…8,9 Although the solubility of substrates was improved by performing the CPO-catalyzed biotransformation in liquid-liquid systems, which composed of a water immiscible organic solvent and water, the catalytic efficiency and selectivity remained lower. 10 The initial enzymatic activity was increased in reverse micelle systems, but inactivation by H 2 O 2 was even more pronounced than that in aqueous media. 11 In terms of practical purpose, improving enzyme catalytic performance by additive is simple and efficient.…”

Section: Introductionmentioning

confidence: 97%

The improvement of chloroperoxidase activities in the presence of ammonium salts and cationic surfactants

Guo

et al. 2010

Biotechnology Progress

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The catalytic activities of chloroperoxidase (CPO) including halogenation, oxidation, and peroxidation were investigated in the presence of ammonium salts: tetramethylammonium bromide (TMABr), tetraethylammonium bromide (TEABr), tetrapropylammonium bromide (TPABr), tetrabutylammonium bromide (TBABr), and cationic surfactants: dodecyltrimethylammonium bromide (DTABr) and cetyltrimethylammonium bromide (CTABr). All the mentioned activities were promoted in most cases. The highest modified activity (ABTS peroxidation) was 18.16 times higher in the presence of TMABr than that in pure buffer. The activity enhancement was strongly dependent on the concentration and the hydrophobic chain length of additives, and the structure of substrates. The kinetic parameters showed that the activation was mainly attributed to an increase in k(cat) due probably to a catalytically favorable conformation of CPO induced by the additives. Moreover, a lower K(m) and higher ratio of k(cat)/K(m) (specificity constant) was obtained, indicating that both the affinity and specificity of CPO to substrates were improved in the presence of additives.

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Chloroperoxidase from Caldariomyces fumago is active in the presence of an ionic liquid as co-solvent

Cited by 65 publications

References 16 publications

Oxidative Halogenation with “Green” Oxidants: Oxygen and Hydrogen Peroxide

Oxidative Halogenation with “Green” Oxidants: Oxygen and Hydrogen Peroxide

Enzymatic hydroxylation of aromatic compounds

The improvement of chloroperoxidase activities in the presence of ammonium salts and cationic surfactants

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