One-way biohydrogen transfer for oxidation of sec-alcohols

Organic Letters

Volumn 10, Issue 11, 2008, Pages 2155-2158

  Lavandera, Iván ^a   Kern, Alexander ^b   Resch, Verena ^a   Ferreira Silva, Bianca ^a   Glieder, Anton ^b   Fabian, Walter M F ^a   De Wildeman, Stefaan ^c   Kroutil, Wolfgang ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^c DSM Pharmaceutical Products   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DEHYDROGENASE; ALCOHOL DERIVATIVE; HYDROGEN; KETONE;

ALPHAPROTEOBACTERIA; ARTICLE; CATALYSIS; CHEMISTRY; ENZYMOLOGY; KINETICS; METABOLISM; OXIDATION REDUCTION REACTION; TIME;

ALCOHOL DEHYDROGENASE; ALCOHOLS; ALPHAPROTEOBACTERIA; CATALYSIS; HYDROGEN; KETONES; KINETICS; OXIDATION-REDUCTION; TIME FACTORS;

EID: 52649137955     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800549f     Document Type: Article

References (43)

1. (a) For recent references, see: Arends, I. W. C. E. Catalytic oxidations in Green Chemistry and Catalysis; Sheldon, R. A., Arends, I. W. C. E., Hanefeld, U., Eds.; Wiley-VCH: Weinheim, 2007.
2. (b) Lenoir, D. Angew. Chem., Int. Ed. 2006, 45, 3206.
3. (c) Modern Oxidation Methods; Bäckvall, J.-E. Ed.; Wiley-VCH: Weinheim, 2004.
4. Some recent examples: (a) Li, Y.-Y.; Zhang, X.-Q.; Dong, Z.-R.; Shen, W.-Y.; Chen, G.; Gao, J.-X. Org. Lett. 2006, 8, 5565.
5. (b) Faller, J. W.; Lavoie, A. R. Org. Lett. 2001, 3, 3703.
6. (c) Persson, B. A.; Larsson, A. L. E.; Le Ray, M.; Bäckvall, J.-E. J. Am. Chem. Soc. 1999, 121, 1645.
7. For reviews, see: (a) Wu, X.; Xiao, J. Chem. Commun. 2007, 2449.
8. (b) Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226.
9. (c) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
10. For a review, see: de Graauw, C. F.; Peters, J. A.; van Bekkum, H. Synthesis 1994, 1007.
11. Trichloroacetaldehyde has been used as quasi-stoichiometric oxidant in a zirconium-catalyzed Oppenauer oxidation: Krohn, K.; Knauer, B.; Küpke, J.; Seebach, D.; Beck, A. K.; Hayakawa, M. Synthesis 1996, 1341.
12. Some recent reviews: (a) Molinari, F. Curr. Org. Chem. 2006, 10, 1247.
13. (b) Kroutil, W.; Mang, H.; Edegger, K.; Faber, K. Adv. Synth. Catal. 2004, 346, 125.
14. (c) Kroutil, W.; Mang, H.; Edegger, K.; Faber, K. Curr. Opin. Chem. Biol. 2004, 8, 120.
15. (d) Thomas, S. M.; DiCosimo, R.; Nagarajan, V Trends Biotechnol. 2002, 20, 238.
16. (e) Nakamura, K.; Matsuda, T.; Harada, T. Chirality 2002, 14, 703.
17. For biocatalytic oxidation coupling an ADH with a NAD(P)H oxidase, see: (a) Riebel, B. R.; Gibbs, P. R.; Wellborn, W. B.; Bommarius, A. S. Adv. Synth. Catal. 2003, 345, 707.
18. (b) Geueke, B.; Riebel, B.; Hummel, W. Enzyme Microb. Technol. 2003, 32, 205.
19. (a) Edegger, K.; Mang, H.; Faber, K.; Gross, J.; Kroutil, W. J. Mol. Catal. A: Chem. 2006, 251, 66.
20. (b) Edegger, K.; Stampfer, W.; Seisser, B.; Faber, K.; Mayer, S. F.; Oehrlein, R.; Hafner, A.; Kroutil, W. Eur. J. Org. Chem. 2006, 1904.
21. (c) Kosjek, B.; Stampfer, W.; van Deursen, R.; Faber, K.; Kroutil, W. Tetrahedron 2003, 59, 9517.
22. (d) Gorrebeeck, C.; Spanoghe, M.; Lanens, D.; Lemière, G. L.; Dommisse, R. A.; Lepoivre, J. A.; Alderweireldt, F. C. Recl. Trav. Chim. Pays-Bas 1991, 110, 231.
23. (e) Snijder-Lambers, A. M.; Vulfson, E. N.; Dodema, H. J. Recl. Trav. Chim. Pays-Bas 1991, 110, 226.
24. (f) Lemière, G. L.; Lepoivre, J. A.; Alderweireldt, F. C. Tetrahedron Lett. 1985, 26, 4527.
25. For employing two enzymes and acetone as hydrogen acceptor see: Fossati, E.; Polentini, F.; Carrea, G.; Riva, S. Biotechnol. Bioeng. 2006, 93, 1216.
26. Performing the oxidation with two enzymes showing opposite stereo-preference is of course a possibility to overcome this limitation but cannot be considered as an elegant method. Furthermore, the corresponding enzymes with opposite enantio-preference are not always accessible.
27. Recent references: (a) Buchholz, S.; Gröger, H. In Biocatalysis in the Pharmaceutical and Biotechnology Industry; Patel, R. N., Ed.; CRC Press: Boca Raton, 2007; p 757.
28. (b) de Wildeman, S. M. A.; Sonke, T.; Schoemaker, H. E.; May, O Acc. Chem. Res. 2007, 40, 1260.
29. (c) Goldberg, K.; Schroer, K.; Lütz, S.; Liese, A. Appl. Microbiol. Biotechnol. 2007, 76, 237.
30. (d) Goldberg, K.; Schroer, K.; Lütz, S.; Liese, A. Appl. Microbiol. Biotechnol. 2007, 76, 249.
31. DSM number refers to strains commercially available from DSMZ (Deutsche Sammlung von Mikroorganismen und Zellkulturen, German Collection of Microorganisms and Cell Cultures, http://www.dsmz.de/).
32. Reisinger, C.; van Assema, F.; Schürmann, M.; Hussain, Z.; Remler, P.; Schwab, H. J. Mol. Catal. B: Enzym. 2006, 39, 149.
33. Polizzi, K. M.; Moore, D. A.; Bommarius, A. S. Chem. Commun. 2007, 1843.
34. 100 g of chloroacetone costs 14 euros at Sigma-Aldrich (Austria).
35. +. See: Edegger, K.; Gruber, C. C.; Poessl, T. M.; Wallner, S. R.; Lavandera, I.; Faber, K.; Niehaus, F.; Eck, J.; Oehrlein, R.; Hafner, A.; Kroutil, W. Chem. Commun. 2006, 2402.
36. Pure compounds had to be synthesized, since the commercial samples had only technical grade.
37. Goldstein, T.; Snow, M. S.; Howard, B. J. J. Mol. Spectrosc. 2006, 236, 1.
38. In a very recent published patent acetoacetate derivatives were used as oxidants: Peschko, C.; Stohrer, J. Wacker Chemie AG, Germany, DE 102006009743, A1 20070906, CAN 2007, 147, 321414.
39. Calculation method used: MP2/cc-pVTZ//MP2/cc-pVDZ.
40. Eckstein, M. F.; Peters, M.; Lembrecht, J.; Spiess, A. C.; Greiner, L. Adv. Synth. Catal. 2006, 348, 1591.
41. (a) Breuer, M.; Ditrich, K.; Habicher, T.; Hauer, B.; Kesseler, M.; Stürmer, R.; Zelinski, T. Angew. Chem., Int. Ed. 2004, 43, 788.
42. (b) Schoemaker, H. E.; Mink, D.; Wubbolts, M. G. Science 2003, 299, 1694.
43. (c) Schmid, A.; Dordick, J. S.; Hauer, B.; Kiener, A.; Wubbolts, M.; Witholt, B. Nature 2001, 409, 258.