Selective Epoxidation of Fatty Acids and Fatty Acid Methyl Esters by Fungal Peroxygenases

被引：26
作者：
Aranda, Carmen [1 ]
Olmedo, Andres [1 ]
Kiebist, Jan [2 ]
Scheibner, Katrin [2 ]
del Rio, Jose C. [1 ]
Martinez, Angel T. [3 ]
Gutierrez, Ana [1 ]
机构：
[1] CSIC, Inst Recursos Nat & Agrobiol Sevilla, Reina Mercedes 10, E-41080 Seville, Spain
[2] JenaBios GmbH, Orlaweg 2, D-00743 Jena, Germany
[3] CSIC, Ctr Invest Biol, Ramiro de Maeztu 9, E-28040 Madrid, Spain
来源：
CHEMCATCHEM | 2018年 / 10卷 / 18期
关键词：
epoxidation; fatty acids; fatty acid methyl esters; fungal peroxygenases; oxidoreductases; COPRINOPSIS-CINEREA; BACILLUS-MEGATERIUM; ALIPHATIC-COMPOUNDS; CYTOCHROME-P450; OXYGENATION; PEROXIDASE; HYDROXYLATION; ALCOHOLS; SYSTEM; OILS;
D O I：
10.1002/cctc.201800849
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Recently discovered fungal unspecific peroxygenases from Marasmius rotula and Chaetomium globosum catalyze the epoxidation of unsaturated fatty acids (FA) and FA methyl esters (FAME), unlike the well-known peroxygenases from Agrocybe aegerita and Coprinopsis cinerea. Reactions of a series of unsaturated FA and FAME with cis-configuration revealed high (up to 100%) substrate conversion and selectivity towards epoxidation, although some significant differences were observed between enzymes and substrates with the best results being obtained with the C. globosum enzyme. This and the M. rotula peroxygenase appear as promising biocatalysts for the environmentally-friendly production of reactive FA epoxides given their self-sufficient monooxygenase activity and the high conversion rate and epoxidation selectivity.
引用
收藏
页码：3964 / 3968
页数：5
相关论文
共 28 条
  • [1] Selective synthesis of the resveratrol analogue 4,4′-dihydroxy-trans-stilbene and stilbenoids modification by fungal peroxygenases
    Aranda, Carmen
    Ullrich, Rene
    Kiebist, Jan
    Scheibner, Katrin
    del Rio, Jose C.
    Hofrichter, Martin
    Martinez, Angel T.
    Gutierrez, Ana
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2018, 8 (09) : 2394 - 2401
  • [2] Steroid Hydroxylation by Basidiomycete Peroxygenases: a Combined Experimental and Computational Study
    Babot, Esteban D.
    del Rio, Jose C.
    Canellas, Marina
    Sancho, Ferran
    Lucas, Fatima
    Guallar, Victor
    Kalum, Lisbeth
    Lund, Henrik
    Groebe, Glenn
    Scheibner, Katrin
    Ullrich, Rene
    Hofrichter, Martin
    Martinez, Angel T.
    Gutiereza, Ana
    [J]. APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2015, 81 (12) : 4130 - 4142
  • [3] Oxyfunctionalization of Aliphatic Compounds by a Recombinant Peroxygenase From Coprinopsis cinerea
    Babot, Esteban D.
    del Rio, Jose C.
    Kalum, Lisbeth
    Martinez, Angel T.
    Gutierrez, Ana
    [J]. BIOTECHNOLOGY AND BIOENGINEERING, 2013, 110 (09) : 2323 - 2332
  • [4] Biermann U., 2011, ANGEW CHEM, V123, P3938
  • [5] Oils and Fats as Renewable Raw Materials in Chemistry
    Biermann, Ursula
    Bornscheuer, Uwe
    Meier, Michael A. R.
    Metzger, Juergen O.
    Schaefer, Hans J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (17) : 3854 - 3871
  • [6] LIPASE CATALYZED SYNTHESIS OF PEROXYCARBOXYLIC ACIDS AND LIPASE MEDIATED OXIDATIONS
    BJORKLING, F
    FRYKMAN, H
    GODTFREDSEN, SE
    KIRK, O
    [J]. TETRAHEDRON, 1992, 48 (22) : 4587 - 4592
  • [7] Specific oxyfunctionalisations catalysed by peroxygenases: opportunities, challenges and solutions
    Bormann, Sebastian
    Baraibar, Alvaro Gomez
    Ni, Yan
    Holtmann, Dirk
    Hollmann, Frank
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2015, 5 (04) : 2038 - 2052
  • [8] Chemical routes for the transformation of biomass into chemicals
    Corma, Avelino
    Iborra, Sara
    Velty, Alexandra
    [J]. CHEMICAL REVIEWS, 2007, 107 (06) : 2411 - 2502
  • [9] Recent advances in the field of selective epoxidation of vegetable oils and their derivatives: a review and perspective
    Danov, S. M.
    Kazantsev, O. A.
    Esipovich, A. L.
    Belousov, A. S.
    Rogozhin, A. E.
    Kanakov, E. A.
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2017, 7 (17) : 3659 - 3675
  • [10] The Paleozoic Origin of Enzymatic Lignin Decomposition Reconstructed from 31 Fungal Genomes
    Floudas, Dimitrios
    Binder, Manfred
    Riley, Robert
    Barry, Kerrie
    Blanchette, Robert A.
    Henrissat, Bernard
    Martinez, Angel T.
    Otillar, Robert
    Spatafora, Joseph W.
    Yadav, Jagjit S.
    Aerts, Andrea
    Benoit, Isabelle
    Boyd, Alex
    Carlson, Alexis
    Copeland, Alex
    Coutinho, Pedro M.
    de Vries, Ronald P.
    Ferreira, Patricia
    Findley, Keisha
    Foster, Brian
    Gaskell, Jill
    Glotzer, Dylan
    Gorecki, Pawel
    Heitman, Joseph
    Hesse, Cedar
    Hori, Chiaki
    Igarashi, Kiyohiko
    Jurgens, Joel A.
    Kallen, Nathan
    Kersten, Phil
    Kohler, Annegret
    Kuees, Ursula
    Kumar, T. K. Arun
    Kuo, Alan
    LaButti, Kurt
    Larrondo, Luis F.
    Lindquist, Erika
    Ling, Albee
    Lombard, Vincent
    Lucas, Susan
    Lundell, Taina
    Martin, Rachael
    McLaughlin, David J.
    Morgenstern, Ingo
    Morin, Emanuelle
    Murat, Claude
    Nagy, Laszlo G.
    Nolan, Matt
    Ohm, Robin A.
    Patyshakuliyeva, Aleksandrina
    [J]. SCIENCE, 2012, 336 (6089) : 1715 - 1719
123