A chemo-enzymatic route to enantiomerically pure cyclic tertiary amines

Journal of the American Chemical Society

Volumn 128, Issue 7, 2006, Pages 2224-2225

  Dunsmore, Colin J ^a   Carr, Reuben ^a   Fleming, Toni ^a   Turner, Nicholas J ^a,b  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA METHYLBENZYLAMINE; AMINE OXIDASE (FLAVIN CONTAINING); ENZYME; POLYAMINE; PYRROLIDINE DERIVATIVE; TERTIARY AMINE;

AMINATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRALITY; DIRECTED MOLECULAR EVOLUTION; ENANTIOMER; RACEMIZATION;

AMINATION; AMINES; ASPERGILLUS NIGER; MONOAMINE OXIDASE; STEREOISOMERISM;

EID: 33644523056     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja058536d     Document Type: Article

References (18)

1. Henderson, K. W. Chem. Commun. 2000, 479.
2. Adamo, M. F. A.; Aggarwal, V. K.; Sage, M. A. J. Am. Chem. Soc. 2000, 122, 8317.
3. Nieuwenhuijzen, J. W.; Grimbergen, R. F. P.; Kellogg, R. M.; Vries, T. R.; Pouwer, K.; van Echten, E.; Kaptein, B.; Hulshof, L. A. Angew. Chem., Int. Ed. 2002, 47, 4281.
4. Bálint, J.; Egri, G.; Czugler, M.; Sehindler, J.; Kiss, V.; Juvancz, Z.; Fogassy. E. Tetrahedron: Asymmetry 2001, 12, 1511.
5. Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 5985.
6. Miyano, S.; Lu, L. D.-L.; Viti, S. M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 4350.
7. (a) Balkenhohl, F.; Ditrich, K.; Hauer, B.; Ladner, W. J. Prakt. Chem. Chem. Ztg. 1997, 339, 381.
8. (b) van Rantwijk, F.; Sheldon, R. A. Tetrahedron 2004, 60, 501.
9. Breen, G. F. Tetrahedron: Asymmetry 2004, 15, 1427.
10. Alexeeva, M.; Enright, A.; Dawson, M. J.; Mahmoudian, M.; Turner, N. J. Angew. Chem., Int. Ed. 2002, 41, 3177.
11. Carr, R.; Alexeeva, M.; Dawson, M. J.; Fernández, V.-G.; Humphrey, C. E.; Turner, N. J. ChemBioChem 2005, 6, 637.
12. For recent approaches, see: (a) Reetz, M. T.; Bocola, M.; Carballeira, J. D.; Zha, D.; Vogel, A. Angew. Chem., Int. Ed. 2005, 44, 4192.
13. (b) Qian, Z.; Lutz, S. J. Am. Chem. Soc. 2005, 127, 13466.
14. Carr, R.; Alexeeva, M.; Enright, A.; Eve, T. S. C.; Dawson, M. J.; Turner, N. J. Angew. Chem., Int. Ed. 2003, 42, 4807.
15. Amines were tested either as racemates or as S-enantiomers according to availability. The MAO-N-5 variant is highly 5-selective as previously observed with all other variants derived from the wild-type enzyme.
16. Brandänge, S.; Lindblom, L.; Pilotti, A.; Rodriguez, B. Acta Chem. Scand. B 1983, 37, 617.
17. Pathak, T.; Thomas, N. F.; Akhtar, M.; Gani, D. Tetrahedron 1990, 46, 1733.
18. Williams, G. D.; Pike, R. A.; Wade, C. E.; Wills, M. Org. Lett. 2003, 5, 4227.