Enzymatic oxidation of alkenes

Marja-Leena Niku-Paavola (Corresponding Author), Liisa Viikari

Research output: Contribution to journalArticleScientificpeer-review

55 Citations (Scopus)

Abstract

Laccase (EC 1.10.3.2) from the white-rot fungus Trametes hirsuta was used to oxidize alkenes. The oxidation was the effect of a two-step process, in which the enzyme first catalyzed the oxidation of primary substrate, the mediator, and then the oxidized mediator oxidized the secondary substrate, the alkene. Three different mediators were studied in the oxidation of aliphatic and cyclic alkenes.

All the alkenes tested were oxidized, but the degree of conversion depended on the alkene and mediator used. The mediators differed from each other in optimal reaction conditions and in specificity towards a given alkene. The best results were obtained by using hydroxybenzotriazole as mediator. Aliphatic polyunsaturated and aromatic allyl alcohols were completely oxidized within 2 h at 20°C. Aliphatic allyl alcohols were oxidized up to 70% at 45°C for 20 h, whereas a conversion of 60% was achieved in 5 h under oxygen atmosphere. By contrast, the oxidation degree of other alkenes, such as allyl ether, cis-2-heptene and cyclohexene, remained low with all the mediators and did not exceed 25%. The major oxidation products in all cases were the corresponding ketones or aldehydes.

Original languageEnglish
Pages (from-to)435 - 444
Number of pages10
JournalJournal of Molecular Catalysis B: Enzymatic
Volume10
Issue number4
DOIs
Publication statusPublished - 2000
MoE publication typeA1 Journal article-refereed

Fingerprint

Alkenes
Olefins
Oxidation
Cycloparaffins
Trametes
Alcohols
Laccase
Substrates
Ketones
Fungi
Atmosphere
Aldehydes
Ether
Ethers
Oxygen
Enzymes

Keywords

  • Enzymatic catalysis
  • Mediated oxidation
  • Oxidation of alkenes
  • Laccase mediator system (LMS)

Cite this

Niku-Paavola, Marja-Leena ; Viikari, Liisa. / Enzymatic oxidation of alkenes. In: Journal of Molecular Catalysis B: Enzymatic. 2000 ; Vol. 10, No. 4. pp. 435 - 444.
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Enzymatic oxidation of alkenes. / Niku-Paavola, Marja-Leena (Corresponding Author); Viikari, Liisa.

In: Journal of Molecular Catalysis B: Enzymatic, Vol. 10, No. 4, 2000, p. 435 - 444.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Enzymatic oxidation of alkenes

AU - Niku-Paavola, Marja-Leena

AU - Viikari, Liisa

PY - 2000

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N2 - Laccase (EC 1.10.3.2) from the white-rot fungus Trametes hirsuta was used to oxidize alkenes. The oxidation was the effect of a two-step process, in which the enzyme first catalyzed the oxidation of primary substrate, the mediator, and then the oxidized mediator oxidized the secondary substrate, the alkene. Three different mediators were studied in the oxidation of aliphatic and cyclic alkenes.All the alkenes tested were oxidized, but the degree of conversion depended on the alkene and mediator used. The mediators differed from each other in optimal reaction conditions and in specificity towards a given alkene. The best results were obtained by using hydroxybenzotriazole as mediator. Aliphatic polyunsaturated and aromatic allyl alcohols were completely oxidized within 2 h at 20°C. Aliphatic allyl alcohols were oxidized up to 70% at 45°C for 20 h, whereas a conversion of 60% was achieved in 5 h under oxygen atmosphere. By contrast, the oxidation degree of other alkenes, such as allyl ether, cis-2-heptene and cyclohexene, remained low with all the mediators and did not exceed 25%. The major oxidation products in all cases were the corresponding ketones or aldehydes.

AB - Laccase (EC 1.10.3.2) from the white-rot fungus Trametes hirsuta was used to oxidize alkenes. The oxidation was the effect of a two-step process, in which the enzyme first catalyzed the oxidation of primary substrate, the mediator, and then the oxidized mediator oxidized the secondary substrate, the alkene. Three different mediators were studied in the oxidation of aliphatic and cyclic alkenes.All the alkenes tested were oxidized, but the degree of conversion depended on the alkene and mediator used. The mediators differed from each other in optimal reaction conditions and in specificity towards a given alkene. The best results were obtained by using hydroxybenzotriazole as mediator. Aliphatic polyunsaturated and aromatic allyl alcohols were completely oxidized within 2 h at 20°C. Aliphatic allyl alcohols were oxidized up to 70% at 45°C for 20 h, whereas a conversion of 60% was achieved in 5 h under oxygen atmosphere. By contrast, the oxidation degree of other alkenes, such as allyl ether, cis-2-heptene and cyclohexene, remained low with all the mediators and did not exceed 25%. The major oxidation products in all cases were the corresponding ketones or aldehydes.

KW - Enzymatic catalysis

KW - Mediated oxidation

KW - Oxidation of alkenes

KW - Laccase mediator system (LMS)

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