Oxidation of pyrene using a hemoglobin-catalyzed biocatalytic reaction

Keum, Hohyun; Kang, Guyoung; Chung, Namhyun

doi:10.1007/s13765-017-0305-9

Cited by 9 publications

(6 citation statements)

References 17 publications

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“…Fenton reaction could be performed in aqueous systems as well as soil [18]. Hb-catalytic system could also be employed for degradation of pyrene in aqueous system and soil as shown in our previous study [15,17]. We also tried to investigate degradation product in soil with much lower organic content (i.e., <10%).…”

Section: Resultsmentioning

confidence: 99%

“…These organic radicals might participate in chemical reactions such as oxidation and polymerization, during which various intermediate products can be formed during detoxification of contaminants [10][11][12][13][14][15]. In our recent study with Hb-catalyzed reaction, when pyrene in liquid solution is oxidatively removed, hydrophilic degradation intermediates are formed [15]. Thus, it is important to show that intermediates formed during the degradation process are less toxic or non-toxic [2,16].…”

Section: Introductionmentioning

confidence: 99%

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Analyses of intermediate products during degradation of pyrene in soil by hemoglobin-catalyzed reaction

Keum

Kang

2018

JABC

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Hemoglobin (Hb) is a member of heme-protein that can perform catalytic non-specific chain reaction in the presence of hydrogen peroxide (H 2 O 2). Catalytic ability of Hb to degrade pyrene was demonstrated using soil contaminated with 14 C pyrene and 10 mg pyrene /kg soil. The composition of soil was similar to previously used soil except that it had lower organic carbon content. Bench scale laboratory tests were conducted in the presence of buffer only, H 2 O 2 only, or Hb with H 2 O 2 for 24 h. After 24 h reaction, 0.1 and 1.3% of 14 C pyrene in contaminated soil were mineralized with H 2 O 2 only or Hb plus H 2 O 2. No mineralization to 14 CO 2 was detected with buffer only. Approximately 12.2% of pyrene was degraded in the presence of H 2 O 2 only while 44.0% of pyrene was degraded in the presence of Hb plus H 2 O 2 during 24 h of catalytic reaction. When degradation intermediate products were examined, two chemicals were observed in the presence of H 2 O 2 only while 25 chemicals were found in the presence of Hb plus H 2 O 2. While most degradation products were simple hydrocarbons, four of the 27 chemicals had aromatic rings. However, none of these four chemicals was structurally related to pyrene. These results suggest that Hb catalytic system could be used to treat pyrene-contaminated soil as an efficient and speedy remediation technology. In addition, intermediate products generated by this system are not greatly affected by composition change in soil organic matter content.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Analyses of intermediate products during degradation of pyrene in soil by hemoglobin-catalyzed reaction

Keum

Kang

2018

JABC

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“…Hemoproteins are promising biocatalysts for synthetic applications that incorporate oxidative reactions (hydroxylation, epoxidation, and sulfoxidation) and carbene‐mediated transformations (olefin cyclopropanation, carbene insertion, and aldehyde olefination) . Hemoglobin, a necessary vehicle for oxygen transport in the body, has been also used in several organic reactions as a stable and abundant biocatalyst, such as lipid peroxidation, aniline hydroxylation, oxidation of hydrogen sulfide and pyrene . Considering the above‐mentioned points and our previous hemoglobin studies, herein we report an efficient and mild hemoglobin‐catalyzed oxidative cyclization for the synthesis of 2‐substituted benzoxazoles (Scheme ).…”

Section: Methodsmentioning

confidence: 95%

“…[19][20][21][22][23][24][25] Hemoglobin, a necessary vehicle for oxygen transport in the body, has been also used in several organic reactions as a stable and abundant biocatalyst, such as lipid peroxidation, aniline hydroxylation, oxidation of hydrogen sulfide and pyrene. [26][27][28][29][30] Considering the above-mentioned points and our previous hemoglobin studies, [31][32] herein we report an efficient and mild hemoglobin-catalyzed oxidative cyclization for the synthesis of 2-substituted benzoxazoles (Scheme 1). To the best of our knowledge, synthesis of 2-substituted benzoxazoles catalyzed by protein has not yet been reported.…”

Section: Hemoglobin: a New Biocatalyst For The Synthesis Of 2-substitmentioning

confidence: 99%

Hemoglobin: A New Biocatalyst for the Synthesis of 2‐substituted Benzoxazoles via Oxidative Cyclization

Tang

et al. 2019

ChemCatChem

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“…Hemoglobins, the most abundant hemoproteins in all groups of organisms, are ideal biocatalysts because of their low cost, commercial availability and good stability. Most studies to date have focused on using hemoglobins to catalyze traditional oxidation reactions and not have found widespread use in catalyzing new types of organic reactions . As part of our studies on the development of hemoprotein‐catalyzed organic reactions, we focused on the synthesis of indolizines catalyzed by hemoglobin via a multicomponent reaction (Scheme ).…”

Section: Methodsmentioning

confidence: 99%

Hemoglobin‐Catalyzed Synthesis of Indolizines Under Mild Conditions

Tang

et al. 2019

Eur J Org Chem

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Hemoglobin-catalyzed synthesis of indolizines via a multicomponent reaction has been reported for the first time. The corresponding indolizines were obtained in moderate to high yields by using this method. This mild, efficient and practical method is distinguished by the use of a commercially inex-Indolizines, a class of heteroaromatic compounds containing two condensed rings (5-and 6-membered) and a bridging nitrogen atom, have been widely applied in natural products and synthetic pharmaceuticals. [1,2] These types of compounds have also been applied as dyes and biological markers due to their photophysical properties. [3][4][5][6][7] Therefore, the development of efficient methods for the synthesis of indolizines continues to attract the attention of organic chemists. Traditional synthetic routes to indolizines mainly comprise the Scholtz or Chichibabin reactions. More recently, cycloaddition reactions (1,3-dipolar cycloadditions), intramolecular cyclizations using acetic anhydride, formation of C3-C4 bond, formation of C1-C9 bond, and formation of C8-C9 bond have been reported. [8][9][10][11][12][13][14] However, most of these methods suffer from some drawbacks, such as the formation of conjugate-acid waste, narrow substrate scope, harsh reaction conditions, need for toxic transition-metal catalysts and harmful organic solvents. Thus, an environmentally preferable and efficient method to synthesize indolizines for practical applications must be developed.Biocatalysis is a highly attractive strategy in organic synthesis for organic synthesis due to its efficient, selective and environment-friendly characteristics. [15] A new biocatalytic approach relies on the promiscuity of enzymes to catalyze reactions that are different than their native functions. This interesting property of protein allows chemists to explore new types of biocatalytic organic reactions and dramatically expands the application of catalytic proteins within the field of organic chemistry. [16][17][18][19][20][21][22] [a]

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Oxidation of pyrene using a hemoglobin-catalyzed biocatalytic reaction

Cited by 9 publications

References 17 publications

Analyses of intermediate products during degradation of pyrene in soil by hemoglobin-catalyzed reaction

Analyses of intermediate products during degradation of pyrene in soil by hemoglobin-catalyzed reaction

Hemoglobin: A New Biocatalyst for the Synthesis of 2‐substituted Benzoxazoles via Oxidative Cyclization

Hemoglobin‐Catalyzed Synthesis of Indolizines Under Mild Conditions

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