Selective oxidations catalyzed by peroxidases

Deurzen, M. P. J. van; Rantwijk, Fred van; Sheldon, Roger A.

doi:10.1016/s0040-4020(97)00477-8

Cited by 268 publications

(138 citation statements)

References 158 publications

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“…This enzyme, a heme-containing peroxidase, has been shown to be unusually useful for selective oxygen insertion reactions which frequently occur in an enantioselective manner. This makes the enzyme a promising candidate for the production of chiral intermediates, such as epoxides, sulfoxides, or halohydrins (Kaup et al, 2007;Park and Clark, 2006;Seelbach et al, 1997;van Deurzen et al, 1997;van Rantwijk and Sheldon, 2000;van de Velde et al, 2001;Zaks and Dodds, 1995).…”

Section: Introductionmentioning

confidence: 99%

Microparticle‐enhanced cultivation of filamentous microorganisms: Increased chloroperoxidase formation by Caldariomyces fumago as an example

Kaup

Ehrich

Pescheck

et al. 2007

Biotech & Bioengineering

129

132

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Microparticle-enhanced cultivation (MPEC) was applied as a novel method for improved biomass and product formation during cultivation of filamentous microorganisms. Exemplarily, chloroperoxidase (CPO) formation by Caldariomyces fumago was analyzed in the presence and absence of microparticles of different size. Particles of $500 mm in diameter had no effect on growth morphology or productivity of CPO formation by C. fumago. In contrast particles of 42 mm in diameter led to the dispersion of the C. fumago mycelia up to the level of single hyphae. Under these conditions the maximum specific productivity of CPO formation was enhanced about fivefold and an accumulated CPO activity in the culture supernatant of more than 1,000 U mL À1 was achieved after 10-12 days of cultivation. In addition, the novel cultivation method also showed a positive effect on growth characteristics of other filamentous microorganisms proven by the stimulation of single hyphae/ cell formation.

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Section: Introductionmentioning

confidence: 99%

Microparticle‐enhanced cultivation of filamentous microorganisms: Increased chloroperoxidase formation by Caldariomyces fumago as an example

Kaup

Ehrich

Pescheck

et al. 2007

Biotech & Bioengineering

129

132

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“…Among them, we would like to highlight peroxidases to perform oxidations [8], or catalases [49,50], to decompose hydrogen peroxide yielding water and molecular oxygen. In many other examples, hydrogen peroxide is a side-product of the target reaction, like in the case of FADH-depending oxidases [51], where the cofactor is regenerated with molecular oxygen producing hydrogen peroxide.…”

mentioning

confidence: 99%

“…In other cases, this oxidant reagent may be used as substrate for peroxidases to obtain regioselective oxidations of really complex and interesting substrates [8]. Hydrogen peroxide may also be used to perform perhydrolysis catalyzed by hydrolases (mainly lipases) to produce peracids, a function quite far from that carried out by lipases in nature and one of the examples of the promiscuity of enzymes [10,63].…”

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confidence: 99%

Hydrogen Peroxide in Biocatalysis. A Dangerous Liaison

Hernández

Berenguer-Murcia²,

Rodrigues³

et al. 2012

COC

140

107

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Hydrogen peroxide is a substrate or side-product in many enzyme-catalyzed reactions. For example, it is a side-product of oxidases, resulting from the re-oxidation of FAD with molecular oxygen, and it is a substrate for peroxidases and other enzymes. However, hydrogen peroxide is able to chemically modify the peptide core of the enzymes it interacts with, and also to produce the oxidation of some cofactors and prostetic groups (e.g., the hemo group). Thus, the development of strategies that may permit to increase the stability of enzymes in the presence of this deleterious reagent is an interesting target. This enhancement in enzyme stability has been attempted following almost all available strategies: site-directed mutagenesis (eliminating the most reactive moieties), medium engineering (using stabilizers), immobilization and chemical modification (trying to generate hydrophobic environments surrounding the enzyme, to confer higher rigidity to the protein or to generate oxidation-resistant groups), or the use of systems capable of decomposing hydrogen peroxide under very mild conditions. If hydrogen peroxide is just a side-product, its immediate removal has been reported to be the best solution. In some cases, when hydrogen peroxide is the substrate and its decomposition is not a sensible solution, researchers coupled one enzyme generating hydrogen peroxide "in situ" to the target enzyme resulting in a continuous supply of this reagent at low concentrations thus preventing enzyme inactivation.This review will focus on the general role of hydrogen peroxide in biocatalysis, the main mechanisms of enzyme inactivation produced by this reactive and the different strategies used to prevent enzyme inactivation caused by this "dangerous liaison". Outlook

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“…195 Significant achiral oxidation can occur in these oxidations which is not catalyzed by CPO; this can be avoided by the use of conditions proposed by Sheldon. 196,197 The first electroenzymatic asymmetric sulfide oxidation was reported using the CPO enzyme from Caldariomyces fumago. 198 A carbon cathode reduces dissolved oxygen to form hydrogen peroxide which, in the presence of CPO can enantioselectively oxidise sulfides to sulfoxides.…”

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confidence: 99%

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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Selective oxidations catalyzed by peroxidases

Cited by 268 publications

References 158 publications

Microparticle‐enhanced cultivation of filamentous microorganisms: Increased chloroperoxidase formation by Caldariomyces fumago as an example

Microparticle‐enhanced cultivation of filamentous microorganisms: Increased chloroperoxidase formation by Caldariomyces fumago as an example

Hydrogen Peroxide in Biocatalysis. A Dangerous Liaison

Synthesis of enantioenriched sulfoxides

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