But-2-ene-1,4-diamine and But-2-ene-1,4-diol as Donors for Thermodynamically Favored Transaminase- and Alcohol Dehydrogenase-Catalyzed Processes

Advanced Synthesis and Catalysis

Volumn 358, Issue 10, 2016, Pages 1618-1624

  Martínez Montero, Lía ^a   Gotor, Vicente ^a   Gotor Fernández, Vicente ^a   Lavandera, Iván ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

alcohol dehydrogenases; atom economy; biocatalysis; cofactor recycling; transaminases

Indexed keywords

EID: 84961285405     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201501066     Document Type: Article

References (54)

1. J. M. Woodley, Curr. Opin. Chem. Biol. 2013, 17, 310–316;
2. U. T. Bornscheuer, G. W. Huisman, R. J. Kazlauskas, S. Lutz, J. C. Moore, K. Robins, Nature 2012, 485, 185–194;
3. D. Muñoz Solano, P. Hoyos, M. J. Hernáiz, A. R. Alcántara, J. M. Sánchez-Montero, Bioresour. Technol. 2012, 115, 196–207;
4. B. M. Nestl, B. A. Nebel, B. Hauer, Curr. Opin. Chem. Biol. 2011, 15, 187–193.
5. Recent bibliography on transaminases:
6. M. Fuchs, J. E. Farnberger, W. Kroutil, Eur. J. Org. Chem. 2015, 6965–6982;
7. R. C. Simon, E. Busto, E.-M. Fischereder, C. S. Fuchs, D. Pressnitz, N. Richter, W. Kroutil, Biocatalysis in Organic Synthesis (Eds.: K. Faber, W.-D. Fessner, N. J. Turner), in: Science of Synthesis, Georg Thieme Verlag, Stuttgart, 2015, pp 383–420;
8. R. C. Simon, N. Richter, E. Busto, W. Kroutil, ACS Catal. 2014, 4, 129–143;
9. W. Kroutil, E.-M. Fischereder, C. S. Fuchs, H. Lechner, F. G. Mutti, D. Pressnitz, A. Rajagopalan, J. H. Sattler, R. C. Simon, E. Siirola, Org. Process Res. Dev. 2013, 17, 751–759;
10. M. Höhne, U. T. Bornscheuer, Enzyme Catalysis in Organic Synthesis, 3rdedn., (Eds.: K. Drauz, H. Gröger, O. May), Wiley-VCH, Weinheim, 2012, pp 779–820;
11. M. S. Malik, E.-S. Park, J.-S. Shin, Appl. Microbiol. Biotechnol. 2012, 94, 1163–1171;
12. S. Mathew, H. Yun, ACS Catal. 2012, 2, 993–1001;
13. D. Koszelewski, K. Tauber, K. Faber, W. Kroutil, Trends Biotechnol. 2010, 28, 324–332;
14. H. C. Hailes, P. A. Dalby, G. J. Lye, F. Baganz, M. Micheletti, N. Szita, J. M. Ward, Curr. Org. Chem. 2010, 14, 1883–1893;
15. D. Zhu, L. Hua, Biotechnol. J. 2009, 4, 1420–1431.
16. Recent bibliography on alcohol dehydrogenases:
17. T. S. Moody, S. Mix, G. Brown, D. Beecher, Biocatalysis in Organic Synthesis, (Eds.: K. Faber, W.-D. Fessner, N. J. Turner), in: Science of Synthesis, Georg Thieme Verlag, Stuttgart, 2015, pp 421–458;
18. Synthetic Methods for Biologically Active Molecules, (Ed.: E. Brenna), Wiley-VCH, Weinheim, 2014;
19. H. Gröger, W. Hummel, S. Borchert, M. Krauβer, Enzyme Catalysis in Organic Synthesis, 3rdedn., (Eds.: K. Drauz, H. Gröger, O. May), Wiley-VCH, Weinheim, 2012, pp 1037–1110;
20. M. M. Musa, R. S. Phillips, Catal. Sci. Technol. 2011, 1, 1311–1323;
21. E. García-Urdiales, I. Alfonso, V. Gotor, Chem. Rev. 2011, 111, PR110–PR180;
22. M. Hall, A. S. Bommarius, Chem. Rev. 2011, 111, 4088–4110;
23. F. Hollmann, I. W. C. E. Arends, D. Holtmann, Green Chem. 2011, 13, 2285–2313;
24. G. W. Huisman, J. Liang, A. Krebber, Curr. Opin. Chem. Biol. 2010, 14, 122–129.
25. M. Richter, Nat. Prod. Rep. 2013, 30, 1324–1345.
26. R. Abu, J. Woodley, ChemCatChem 2015, 7, 3094–3105;
27. E. E. Ferrandi, D. Monti, S. Riva, Cascade Biocatalysis, (Eds.: S. Riva, W.-D. Fessner), Wiley-VCH, Weinheim, 2014, pp 23–42;
28. S. Kara, J. H. Schrittwieser, F. Hollmann, M. B. Ansorge-Schumacher, Appl. Microbiol. Biotechnol. 2014, 98, 1517–1529;
29. W. Hummel, H. Gröger, J. Biotechnol. 2014, 191, 22–31;
30. T. Quinto, V. Köhler, T. R. Ward, Top. Catal. 2014, 57, 321–331;
31. H. Wu, C. Tian, X. Song, C. Liu, D. Yang, Z. Jiang, Green Chem. 2013, 15, 1773–1789;
32. C. Rodríguez, I. Lavandera, V. Gotor, Curr. Org. Chem. 2012, 16, 2525–2541;
33. F. Hollmann, I. W. C. E. Arends, K. Buehler, ChemCatChem 2010, 2, 762–782.
34. W. Kroutil, H. Mang, K. Edegger, K. Faber, Curr. Opin. Chem. Biol. 2004, 8, 120–126.
35. K. E. Cassimjee, C. Branneby, V. Abedi, A. Wells, P. Berglund, Chem. Commun. 2010, 46, 5569–5571.
36. R. Zuhse, C. Leggewie, F. Hollmann, S. Kara, Org. Process Res. Dev. 2015, 19, 369–372;
37. S. Kara, D. Spickermann, A. Weckbecker, C. Leggewie, I. W. C. E. Arends, F. Hollmann, ChemCatChem 2014, 6, 973–976;
38. S. Kara, D. Spickermann, J. H. Schrittwieser, C. Leggewie, W. J. H. van Berkel, I. W. C. E. Arends, F. Hollmann, Green Chem. 2013, 15, 330–335.
39. A. Bornadel, R. Hatti-Kaul, F. Hollmann, S. Kara, ChemCatChem 2015, 7, 2442–2445.
40. B. Wang, H. Land, P. Berglund, Chem. Commun. 2013, 49, 161–163.
41. A. P. Green, N. J. Turner, E. O. Reilly, Angew. Chem. 2014, 126, 10890–10893;
42. Angew. Chem. Int. Ed. 2014, 53, 10714–10717.
43. E. Fabiano, B. T. Golding, M. M. Sadeghi, Synthesis 1987, 190–192.
44. B. Martin, F. Possémé, C. Le Barbier, F. Carreaux, B. Carboni, N. Seiler, J.-P. Moulinoux, J.-G. Delcros, Bioorg. Med. Chem. 2002, 10, 2863–2871.
45. T. V. Vernitskaya, O. N. Efimov, Russ. Chem. Rev. 1997, 66, 443–457.
46. D. Baud, N. Ladkau, T. S. Moody, J. M. Ward, H. C. Hailes, Chem. Commun. 2015, 51, 17225–17228.
47. D. Könning, W. Hiller, M. Christmann, Org. Lett. 2012, 14, 5258–5261.
48. C. E. Paul, M. Rodríguez-Mata, E. Busto, I. Lavandera, V. Gotor-Fernández, V. Gotor, S. García-Cerrada, J. Mendiola, O. de Frutos, I. Collado, Org. Process Res. Dev. 2014, 18, 788–792.
49. See, for instance:
50. D. J. St. Jean Jr, C. Yuan, E. A. Bercot, R. Cupples, M. Chen, J. Fretland, C. Hale, R. W. Hungate, R. Komorowski, M. Veniant, M. Wang, X. Zhang, C. Fotsch, J. Med. Chem. 2007, 50, 429–432;
51. Y.-J. Wu, H. He, L.-Q. Sun, A. L′Heureux, J. Chen, P. Dextraze, J. E. Starrett, Jr., C. G. Boissard, V. K. Gribkoff, J. Natale, S. I. Dworetzky, J. Med. Chem. 2004, 47, 2887–2896;
52. F. C. Y. Chan, G. A. Potter, S. E. Barrie, B. P. Haynes, M. G. Rowlands, J. Houghton, M. Jarman, J. Med. Chem. 1996, 39, 3319–3323.
53. It must be noted that this approach is a simplified study just taking into account the waste generated in the stereoselective amination reaction regarding the amine donor employed. To depict a general overview of the atom and cost efficiencies, more accurate calculations such as the E factor should be performed. For more information, see: Y. Ni, D. Holtmann, F. Hollmann, ChemCatChem 2014, 6, 930–943.
54. EATOS: Environmental Assessment Tool for Organic Syntheses, http://www.metzger.chemie.uni-oldenburg.de/eatos/english.htm, accessed: 05.02. 2014.