A Process Concept for High-Purity Production of Amines by Transaminase-Catalyzed Asymmetric Synthesis: Combining Enzyme Cascade and Membrane-Assisted ISPR

Organic Process Research and Development

Volumn 19, Issue 7, 2015, Pages 793-799

  Börner, Tim ^a   Rehn, Gustav ^b   Grey, Carl ^a   Adlercreutz, Patrick ^a  

^a LUND UNIVERSITY   (Sweden)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CATALYSIS; ENZYMES; KETONES; REACTION RATES;

ASYMMETRIC SYNTHESIS; CATALYZED SYNTHESIS; DONOR SUBSTRATES; MAXIMUM REACTION RATE; MEMBRANE EXTRACTION; PROOF OF CONCEPT; REDUCTIVE AMINATION; SITU PRODUCT REMOVAL;

AMINES;

EID: 84937153016     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/acs.oprd.5b00055     Document Type: Article

References (43)

1. Turner, C. Biocatalysis in the Pharmaceutical and Biotechnology Industries; CES Press LLC: Boca Raton, FL, 2007.
2. Patel, R. N. ACS Catal. 2011, 1, 1056-1074
3. Ghislieri, D.; Turner, N. Top Catal. 2014, 57, 284-300
4. Shin, J.-S.; Kim, B.-G. Biotechnol. Bioeng. 1999, 65, 206-211
5. Kohls, H.; Steffen-Munsberg, F.; Höhne, M. Curr. Opin. Chem. Biol. 2014, 19, 180-192
6. Savile, C. K.; Janey, J. M.; Mundorff, E. C.; Moore, J. C.; Tam, S.; Jarvis, W. R.; Colbeck, J. C.; Krebber, A.; Fleitz, F. J.; Brands, J.; Devine, P. N.; Huisman, G. W.; Hughes, G. J. Science 2010, 329, 305-309
7. Nestl, B. M.; Hammer, S. C.; Nebel, B. A.; Hauer, B. Angew. Chem., Int. Ed. 2014, 53, 3070-3095
8. Nugent, T. C.; El-Shazly, M. Adv. Synth. Catal. 2010, 352, 753-819
9. Shin, J.-S.; Kim, B.-G. Biotechnol. Bioeng. 2002, 77, 832-837
10. Eliot, A.; Kirsch, J. Annu. Rev. Biochem. 2004, 73, 383-415
11. Abrahamson, M. J.; Vázquez-Figueroa, E.; Woodall, N. B.; Moore, J. C.; Bommarius, A. S. Angew. Chem., Int. Ed. 2012, 51, 3969-3972
12. Scheller, P. N.; Fademrecht, S.; Hofelzer, S.; Pleiss, J.; Leipold, F.; Turner, N. J.; Nestl, B. M.; Hauer, B. ChemBioChem. 2014, 15, 2201-2204
13. Koszelewski, D.; Lavandera, I.; Clay, D.; Rozzell, D.; Kroutil, W. Adv. Synth. Catal. 2008, 350, 2761-2766
14. Scha¨tzle, S.; Steffen-Munsberg, F.; Thontowi, A.; Höhne, M.; Robins, K.; Bornscheuer, U. T. Adv. Synth. Catal. 2011, 353, 2439-2445
15. Sayer, C.; Isupov, M. N.; Westlake, A.; Littlechild, J. A. Acta Crystallogr., D 2013, 69, 564-576
16. Tufvesson, P.; Jensen, J. S.; Kroutil, W.; Woodley, J. M. Biotechnol. Bioeng. 2012, 109, 2159-2162
17. Koszelewski, D.; Tauber, K.; Faber, K.; Kroutil, W. Trends Biotechnol. 2010, 28, 324-332
18. Kroutil, W.; Fischereder, E.-M.; Fuchs, C. S.; Lechner, H.; Mutti, F. G.; Pressnitz, D.; Rajagopalan, A.; Sattler, J. H.; Simon, R. C.; Siirola, E. Org. Process Res. Dev. 2013, 17, 751-759
19. Mathew, S.; Yun, H. ACS Catal. 2012, 2, 993-1001
20. Yun, H.; Cho, B.-K.; Kim, B.-G. Biotechnol. Bioeng. 2004, 87, 772-778
21. Park, E.-S.; Dong, J.-Y.; Shin, J.-S. Org. Biomol. Chem. 2013, 11, 6929
22. Tufvesson, P.; Bach, C.; Woodley, J. M. Biotechnol. Bioeng. 2014, 111, 309-319
23. Ricca, E.; Brucher, B.; Schrittwieser, J. H. Adv. Synth. Catal. 2011, 353, 2239-2262
24. Simon, R. C.; Richter, N.; Busto, E.; Kroutil, W. ACS Catal. 2013, 4, 129-143
25. Pressnitz, D.; Fuchs, C. S.; Sattler, J. H.; Knaus, T.; Macheroux, P.; Mutti, F. G.; Kroutil, W. ACS Catal. 2013, 3, 555-559
26. Wang, B.; Land, H.; Berglund, P. Chem. Commun. 2013, 49, 161-163
27. Tufvesson, P.; Lima-Ramos, J.; Jensen, J. S.; Al-Haque, N.; Neto, W.; Woodley, J. M. Biotechnol. Bioeng. 2011, 108, 1479-1493
28. Truppo, M. D.; Rozzell, J. D.; Turner, N. J. Org. Process Res. Dev. 2010, 14, 234-237
29. Andrade, L. H.; Kroutil, W.; Jamison, T. F. Org. Lett. 2014, 16, 6092-6095
30. Shin, J.-S.; Kim, B.-G.; Liese, A.; Wandrey, C. Biotechnol. Bioeng. 2001, 73, 179-187
31. Yun, H.; Kim, B.-G. Biosci. Biotechnol. Biochem. 2008, 72, 3030-3033
32. Rehn, G.; Adlercreutz, P.; Grey, C. J. Biotechnol. 2014, 179, 50-55
33. Rehn, G. ω-Transaminase catalyzed synthesis of chiral amines. Ph.D. Dissertation, Lund University, Sweden, 2013.
34. Mutti, F. G.; Kroutil, W. Adv. Synth. Catal. 2012, 354, 3409-3413
35. Rehn, G.; Grey, C.; Branneby, C.; Adlercreutz, P. J. Biotechnol. 2013, 165, 138-144
36. Shin, J.-S.; Kim, B.-G. Biosci. Biotechnol. Biochem. 2001, 65, 1782-1788
37. Turner, N. J.; Truppo, M. D. Biocatalytic Routes to Nonracemic Chiral Amines. In Chiral Amine Synthesis; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2010; pp 431-459.
38. Truppo, M. D.; Strotman, H.; Hughes, G. ChemCatChem 2012, 4, 1071-1074
39. Fuchs, C. S.; Simon, R. C.; Riethorst, W.; Zepeck, F.; Kroutil, W. Bioorg. Med. Chem. 2014, 22, 5558-5562
40. Simon, R. C.; Fuchs, C. S.; Lechner, H.; Zepeck, F.; Kroutil, W. Eur. J. Org. Chem. 2013, 2013, 3397-3402
41. Mutti, F. G.; Fuchs, C. S.; Pressnitz, D.; Sattler, J. H.; Kroutil, W. Adv. Synth. Catal. 2011, 353, 3227-3233
42. Shin, J.-S.; Kim, B.-G. Biotechnol. Bioeng. 1997, 55, 348-358
43. Baumann, M.; Baxendale, I. R. Beilstein J. Org. Chem. 2013, 9, 2265-2319