Iron catalysis for in situ regeneration of oxidized cofactors by activation and reduction of molecular oxygen: A synthetic metalloporphyrin as a biomimetic NAD(P)H oxidase

Angewandte Chemie - International Edition

Volumn 50, Issue 10, 2011, Pages 2397-2400

  Maid, Harald ^a   Böhm, Philipp ^a   Huber, Stefan M ^a   Bauer, Walter ^a   Hummel, Werner ^b   Jux, Norbert ^a   Gröger, Harald ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Cofactors; Enzyme catalysis; Iron; Iron catalysis; Porphyrins

Indexed keywords

AQUEOUS SOLUTIONS; COFACTORS; ENZYMATIC OXIDATIONS; ENZYME CATALYSIS; IN-SITU; IRON CATALYSIS; METALLOPORPHYRINS; NAD(P)H; NON-ENZYMATIC;

BIOMIMETICS; CATALYSTS; ENZYMES; MOLECULAR OXYGEN; PORPHYRINS;

CATALYSIS;

IRON; METALLOPORPHYRIN; OXYGEN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE OXIDASE;

ARTICLE; CATALYSIS; CHEMISTRY; COENZYME; METABOLISM; OXIDATION REDUCTION REACTION; SYNTHESIS;

CATALYSIS; COENZYMES; IRON; METALLOPORPHYRINS; NADPH OXIDASE; OXIDATION-REDUCTION; OXYGEN;

EID: 79952053501     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201004101     Document Type: Article

References (32)

1. a) Overview about biomimetic catalysis: Artificial Enzymes (Ed.: R. Breslow), Wiley-VCH, Weinheim, 2005;
2. b) Review: A. Weckbecker, H. Gröger, W. Hummel, Adv. Biochem. Engin./Biotechnol. 2010, 120, 195-242.
3. D. Westerhausen, S. Herrmann, W. Hummel, E. Steckhan, Angew. Chem. 1992, 104, 1496-1498;
4. Angew. Chem. Int. Ed. Engl. 1992, 31, 1529-1531.
5. a) W. Hummel, M. Kuzu, B. Geueke, Org. Lett. 2003, 5, 3649-3650;
6. b) B. Geueke, B. Riebel, W. Hummel, Enzyme Microb. Technol. 2003, 32, 205-211;
7. c) B. R. Riebel, P. R. Gibbs, W. B. Wellborn, A. S. Bommarius, Adv. Synth. Catal. 2003, 345, 707-712;
8. d) W. Hummel, B. Riebel, Biotechnol. Lett. 2003, 25, 51-54;
9. B. R. Riebel, P. R. Gibbs,W. B.Wellborn, A. S. Bommarius, Adv. Synth. Catal. 2002, 344, 1156-1168.
10. An interesting example of a chemoenzymatic cofactor-regeneration was recently reported in: S. L. Pival, M. Klimacek, B. Nidetzky, Adv. Synth. Catal. 2008, 350, 2305-2312.
11. I. Schröder, E. Steckhan, A. Liese, J. Electroanal. Chem. 2003, 541, 109-115.
12. G. Hilt, B. Lewall, G. Montero, J. H. P. Utley, E. Steckhan, Liebigs Ann. 1997, 2289-2296.
13. a) I. Schlichting, J. Berendzen, K. Chu, A. M. Stock, S. A. Maves, D. E. Benson, R. M. Sweet, D. Ringe, G. A. Petsko, S. G. Sligar, Science 2000, 287, 1615-1622;
14. b) K. Faber, Biotransformations in Organic Chemistry, 5th ed., Springer, Berlin, 2004, pp. 227-230.
15. A corresponding manganese complex containing this ligand turned out to be suitable for the transformation of synthetic dihydropyridine derivatives using flavin mononucleotide (FMN) as an electron carrier: I. Tabushi, M. Kodera, J. Am. Chem. Soc. 1986, 108, 1101-1103.
16. For a review about bioinspired and biomimetic iron-catalyzed reactions, see: S. Enthaler, K. Junge, M. Beller, Angew. Chem. 2008, 120, 3363-3367;
17. Angew. Chem. Int. Ed. 2008, 47, 3317-3321.
18. J.-E. Jee, S. Eigler, N. Jux, A. Zahl, R. van Eldik, Inorg. Chem. 2007, 46, 3336-3352.
19. a) Pioneering work in synthesis and characterization of iron TSPP complex 4: E. B. Fleischer, J. M. Palmer, T. S. Srivastava, A. Chatterjee, J. Am. Chem. Soc. 1971, 93, 3162-3167;
20. b) The iron TSPP complex 4 is commercially available from TriPorTech GmbH, Germany (product abbreviation: TSPP-FeIII ; product number: TPT00142617).
21. Hitherto existing applications of metalloporphyrin complexes in oxidation reactions were either based on non-natural nicotinamide derivatives serving as NADH analogues or proceeded using oxidants other than oxygen, for example, hydrogen peroxide, organic peroxides, and iodosylbenzene. See: a) reference [8];
22. b) S. Othman, V. Mansuy-Mouries, C. Bensoussan, P. Battioni, D. Mansuy, C. R. Chim. 2000, 3, 751-755;
23. c) G. de Freitas Silva, D. C. da Silva, A. S. Guimaraes, E. do Nascimento, J. S. Reboucas, M. P. de Araujo, M. E. M. D. de Carvalho, Y. M. Idemori, J. Mol. Catal. A 2007, 266, 274-283.
24. The development of synthetic methods for the production of sugar acids is of fundamental interest because of their versatile applications. For example, the industrial chemical d-gluconic acid, which is biotechnologically produced starting from dglucose on a 100000 ton scale per year, is widely used in the food, metal, and textile industry. For a recently developed highly efficient chemocatalytic alternative, see: a) A. Mirescu, U. Prüße, Catal. Commun. 2006, 7, 11-17;
25. b) C. Baatz, U. Prüße, Catal. Today 2007, 122, 325-329.
26. H. Maid, S. Huber, P. Böhm, H. Gröger, unpublished results.
27. The alcohol dehydrogenase catalyzed oxidation of cyclooctanol was previously performed with an enzymatic in situ regeneration of the cofactor: a) T. Itozawa, H. Kise, Biotechnol. Lett. 1993, 15, 843-846;
28. b) G. L. Lemiere, J. A. Lepoivre, F. C. Alderweireldt, Bioorg. Chem. 1988, 16, 165-174.
29. For the formation of related iron(III) porphyrin complexes starting from iron(III) porphyrin and sodium borohydride as a hydride donor, see: J.-i. Setsune, Y. Ishimaru, A. Sera, Chem. Lett. 1992, 377-380.
30. The formation of related iron(III) hydroperoxyl, iron(III) peroxo, and iron(IV) oxo complexes as reactive intermediates was also described in connection with the reaction mechanisms of enzymatic hydroxylations with heme-containing P450 monooxygenases and nonheme-containing monooxygenases; for selected contributions, see: a) reference [7];
31. b) L. Que, Jr., J.Biol. Inorg. Chem. 2004, 9, 643-690;
32. c) L. Que, Jr., W. B. Tolman, Nature 2008, 455, 333-340.