Monoamine oxidase (MAO-N) catalyzed deracemization of tetrahydro-β- carbolines: Substrate dependent switch in enantioselectivity

ACS Catalysis

Volumn 3, Issue 12, 2013, Pages 2869-2872

  Ghislieri, Diego ^a   Houghton, Deborah ^a   Green, Anthony P ^a   Willies, Simon C ^a   Turner, Nicholas J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

carbolines; biocatalysis; chiral amine; deracemization; monoamine oxidase

Indexed keywords

BIOCATALYSIS; CARBOLINES; CHIRAL AMINES; DE-RACEMIZATION; MONOAMINE OXIDASE;

ASPERGILLUS; ENANTIOMERS; ENANTIOSELECTIVITY; ENZYMES; STEREOCHEMISTRY;

PYRIDINE;

EID: 84890423869     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs400724g     Document Type: Article

References (18)

1. Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023
2. Martin, S. F.; Rüeger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124
3. Lögers, M.; Overman, L. E.; Welmaker, G. S. J. Am. Chem. Soc. 1995, 117, 9139
4. Mergott, D. J.; Zuend, S. J.; Jacobsen, E. N. Org. Lett. 2008, 10, 745
5. Gremmen, C.; Willemse, B.; Wanner, M. J.; Koomen, G. J. Org. Lett. 2000, 2, 1955
6. Chen, X. C.; Zhu, J. P. Angew. Chem., Int. Ed. 2007, 46, 3962
7. Li, C.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 13208
8. Roszkowski, P.; Wojtasiewicz, K.; Leniewski, A.; Maurin, J. K.; Lis, T.; Czarnocki, Z. J. Mol. Catal. A: Chem. 2005, 232, 143
9. Wu, J. S.; Wang, F.; Ma, Y. P.; Cui, X. C.; Cun, L. F.; Zhu, J.; Deng, J. G.; Yu, B. L. Chem. Commun. 2006, 1766
10. Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558
11. Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, 126, 1086
12. Espinoza-Moraga, M.; Petta, T.; Vasquez-Vasquez, M.; Felipe Laurie, V.; Moraes, L. A. B.; Silva Santos, L. Tetrahedron: Asymmetry 2010, 21, 1988
13. Bernhardt, P.; Usera, A. R.; O'Connor, S. E. Tetrahedron Lett. 2010, 51, 4400
14. Leipold, F.; Hussain, S.; Ghislieri, D.; Turner, N. J. ChemCatChem 2013, 10.1002/cctc.201300539
15. Alexeeva, M.; Enright, A.; Dawson, M. J.; Mahmoudian, M.; Turner, N. J. Angew. Chem., Int. Ed. 2002, 41, 3177
16. Carr, R.; Alexeeva, M.; Enright, A.; Eve, T. S. C.; Dawson, M. J.; Turner, N. J. Angew. Chem., Int. Ed. 2003, 42, 4807
17. Dunsmore, C. J.; Carr, R.; Fleming, T.; Turner, N. J. J. Am. Chem. Soc. 2006, 128, 2224
18. Ghislieri, D.; Green, A. P.; Pontini, M.; Willies, S. C.; Rowles, I.; Frank, A.; Grogan, G.; Turner, N. J. J. Am. Chem. Soc. 2013, 135, 10863