Probing the scope of the sulfoxidation activity of vanadium bromoperoxidase from Ascophyllum nodosum

Brink, Hilda B. ten; Holland, Herbert L.; Lingen, Hester van; Wever, Ron

doi:10.1016/s0957-4166(99)00514-5

Cited by 57 publications

(23 citation statements)

References 46 publications

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“…[26,27] These stable enzymes have already been shown to have high potential for application in organic synthesis: vanadium bromoperoxidases have been shown to perform enantioselective sulphoxidation [28±31] of a series of compounds of which both R and S enantiomeric excess can be formed, depending on which enzyme is used. [30] A disadvantage of vanadium bromoperoxidase (VBPO) from the seaweed Ascophyllum nodosum is that it experiences slow inactivation during 1 O 2 production. [18] This inactivation is likely to be worse at high H 2 O 2 concentrations at which this enzyme (at low pH values) is inactivated by oxidation of a critical histidine.…”

Section: Introductionmentioning

confidence: 99%

Vanadium Chloroperoxidase as a Catalyst for Hydrogen Peroxide Disproportionation to Singlet Oxygen in Mildly Acidic Aqueous Environment

Renirie

Pierlot²,

Aubry³

et al. 2003

Adv Synth Catal

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Chemiluminescence studies show that the enzyme vanadium chloroperoxidase from the fungus Curvularia inaequalis is a highly efficient catalyst for the production of singlet oxygen from hydrogen peroxide in a mildly acidic aqueous environment, with a maximum turnover frequency of 100 s À1 with respect to H 2 O 2 consumption. The enzyme studied here can be regarded as a supplementary catalyst to inorganic molybdate, which operates in basic aqueous media. The enzyme system is 10 3 ± 10 4 times faster than the molybdate system when compared at their optimal pH. The enzyme is very stable against singlet oxygen, in contrast to heme-containing peroxidases which, due to inactivation by singlet oxygen, only produce a short burst, presumably by oxidation of the labile cofactor. The vanadium chloroperoxidase was compared with vanadium bromoperoxidase from the seaweed Ascophyllum nodosum and was found to be even more stable; it is stable towards a continuous flow of singlet oxygen for at least 1 hour and also it is not inactivated by 500 mM H 2 O 2 . An important difference with vanadium bromoperoxidase is that the vanadium chloroperoxidase is able to effectively use chloride as a cocatalyst (20 s À1) instead of bromide. This offers an important advantage from an application point of view; using chloride, no side products are observed when the chemical trap anthracene-9,10-bis(ethanesulphonate) is fully converted by singlet oxygen into its corresponding endoperoxide. By contrast, when bromide is used, 20% side product is formed. During the conversion the enzyme remains fully stable for 25,000 turnovers.

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Section: Introductionmentioning

confidence: 99%

Vanadium Chloroperoxidase as a Catalyst for Hydrogen Peroxide Disproportionation to Singlet Oxygen in Mildly Acidic Aqueous Environment

Renirie

Pierlot²,

Aubry³

et al. 2003

Adv Synth Catal

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“…The absence of bromotryptophan in the hypobranchial glands (71) and evidence for posttranslational bromination at the 6-position of tryptophan in a sea snail (Conus radiatus) (72) support this hypothesis. Moreover, bromoperoxidase and vanadium bromoperoxidase have been found in some algal species (73) and could be the enzymes involved (Scheme 11).…”

Section: Precursors and Biosynthesismentioning

confidence: 99%

“…o-Nitro-toluene (72) is brominated at the meta-position of the nitro group by action of bromine in the presence of iron to form 69. The methyl group is then halogenated by action of N-bromosuccinimide and the bromine further displaced by pyridine to form the corresponding pyridinium salt (73). The latter is converted to the nitroso derivative 74, which by hydrolysis under strong acidic (17).…”

Section: Chemical Synthesis Of Tyrian Purplementioning

confidence: 99%

A Colorful History: The Evolution of Indigoids

Gaboriaud‐Kolar

Nam

Skaltsounis

2014

Progress in the Chemistry of Organic Natural Products

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“…210 Better enantioselectivity was observed preparing aryl sulfoxides which contained activating substituents at the para position of the aromatic ring. The sulfoxide 173 was obtained in 89% ee.…”

Section: Scheme 70mentioning

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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Probing the scope of the sulfoxidation activity of vanadium bromoperoxidase from Ascophyllum nodosum

Cited by 57 publications

References 46 publications

Vanadium Chloroperoxidase as a Catalyst for Hydrogen Peroxide Disproportionation to Singlet Oxygen in Mildly Acidic Aqueous Environment

Vanadium Chloroperoxidase as a Catalyst for Hydrogen Peroxide Disproportionation to Singlet Oxygen in Mildly Acidic Aqueous Environment

A Colorful History: The Evolution of Indigoids

Synthesis of enantioenriched sulfoxides

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