Synthesis and microbial transformation of β-amino nitriles

Tetrahedron

Volumn 61, Issue 17, 2005, Pages 4249-4260

  Winkler, Margit ^a   Martínková, Ludmila ^b   Knall, Astrid C ^a   Krahulec, Stefan ^a   Klempier, Norbert ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^b INSTITUTE OF MICROBIOLOGY   (Czech Republic)

Author keywords

Enantioselectivity; Microbial nitrile hydrolysis; Amino acids

Indexed keywords

2 (TOLUENE 4 SULFONYLAMINO)CYCLOHEXANE CARBOXYLIC ACID; 2 (TOLUENE 4 SULFONYLAMINO)CYCLOPENTANE CARBOXAMIDE; 2 BENZOYLAMINOCYCLOHEXANE CARBOXYLIC ACID; AMIDE; BENZAMIDE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; N (1 BENZYL 2 CYANOETHYL) 4 METHYLBENZENESULFONAMIDE; N (2 CARBAMOYLCYCLOPENTYL)BENZAMIDE; N (2 CYANO 1 PHENYL 2 PROPENYL) 4 METHYLBENZENESULFONAMIDE; N (2 CYANO 1 PHENYLETHYL) 4 METHYLBENZENESULFONAMIDE; N (2 CYANOCYCLOHEXYL) 4 METHYLBENZENESULFONAMIDE; N (2 CYANOCYCLOHEXYL)BENZAMIDE; N (2 CYANOCYCLOPENTYL) 4 METHYLBENZENESULFONAMIDE; N (2 CYANOCYCLOPENTYL)BENZAMIDE; NITRILE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CHEMICAL ANALYSIS; MICROBIAL METABOLISM; PRIORITY JOURNAL; RHODOCOCCUS EQUI; RHODOCOCCUS ERYTHROPOLIS; SYNTHESIS;

ERYTHROPOLIS; RHODOCOCCUS EQUI; RHODOCOCCUS ERYTHROPOLIS; RHODOCOCCUS SP.;

EID: 16244385920     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.02.057     Document Type: Article

References (28)

1. E. Juaristi Enantioselective Synthesis of β-Amino Acids 1997 Wiley-VCH London
2. G. Cardillo, and C. Tomasini Chem. Soc. Rev. 25 1996 117 128
3. D. Seebach, S. Abele, K. Gademann, G. Guichard, T. Hintermann, B. Jaun, J.L. Matthews, and J.V. Schreiber Helv. Chim. Acta 81 1998 932 982
4. R.P. Cheng, S.H. Gellman, and W.F. DeGrado Chem. Rev. 101 2001 3219 3232
5. T.A. Martinek, and F. Fülöp Eur. J. Biochem. 270 2003 3657 3666
6. M. Konishi, M. Nishio, K. Saitoh, T. Miyaki, T. Oki, and H. Kawaguchi J. Antibiot. 42 1989 1749 1755
7. Z. Szakonyi, F. Fülöp, G. Bernáth, G. Török, and A. Péter Tetrahedron: Asymmetry 9 1998 993 999
8. M. Liu, and M.P. Sibi Tetrahedron 58 2002 7991 8035
9. D.C. Cole Tetrahedron 50 1994 9517 9582
10. F. Fülöp Chem. Rev. 101 2001 2181 2204
11. N. Sewald Angew. Chem., Int. Ed. 42 2003 5794 5795
12. L. Martínková, and V. Křen Biocatal. Biotrans. 20 2002 73 93
13. C. Brenner Curr. Opin. Struct. Biol. 12 2002 775 782
14. M. Kobayashi, and S. Shimizu Curr. Opin. Chem. Biol. 4 2000 95 102
15. M. Preiml, K. Hillmayer, and N. Klempier Tetrahedron Lett. 44 2003 5057 5059
16. M. Preiml, H. Hönig, and N. Klempier J. Mol. Catal. B: Enzym. 29 2004 115 121
17. L. Martínková, N. Klempier, M. Preiml, M. Ovesná, M. Kuzma, V. Mylerová, and V. Křen Can. J. Chem. 80 2002 724 727
18. M.-X. Wang, and Y. Wu Org. Biomol. Chem. 1 2003 535 540
19. A. Péter, G. Török, and D.W. Armstrong J. Chromatogr. 793 1998 283 296
20. A. Péter, G. Török, P. Csomós, M. Péter, G. Bernáth, and F. Fülöp J. Chromatogr. 761 1997 103 113
21. I. Prepechalová, L. Martínková, A. Stolz, M. Ovesná, K. Bezouska, J. Kopecký, and V. Kren Appl. Microbiol. Biotechnol. 55 2001 150 156
22. J.K. Williams J. Org. Chem. 28 1963 1054 1059
23. J. Wu, X.-L. Hou, and L.-X. Dai J. Org. Chem. 65 2000 1344 1348
24. D. Balan, and H. Adolfsson J. Org. Chem. 67 2002 2329 2334
25. E. Atay, I.B. Blagoeva, F.L. Chubb, J.T. Edward, I.G. Pojarlieff, and M.M. Toteva Can. J. Chem. 78 2000 84 94
26. J.F. Berrien, J. Royer, and H.P. Husson J. Org. Chem. 59 1994 3769 3774
27. M.J. DiGeronimo, and A.D. Antoine Appl. Environ. Microbiol. 31 1976 900 906
28. CCDC 246741 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.