Chemoenzymatic synthesis of (4S)- and (4R)-4-methyl-2-oxoglutaric acids, precursors of glutamic acid analogues

European Journal of Organic Chemistry

Volumn , Issue 12, 1999, Pages 3403-3406

  Helaine, Virgil ^a   Bolte, Jean ^a  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

Amino acids; Aminotransferase; Enzyme catalysis; Glutamate; Oxoglutarate

Indexed keywords

2 OXOGLUTARIC ACID; AMINOTRANSFERASE; GLUTAMATE RECEPTOR; GLUTAMIC ACID DERIVATIVE;

ALKYLATION; AMINATION; ARTICLE; CATALYSIS; ENZYME ACTIVITY; ENZYME MECHANISM; HYDROLYSIS; NEUROCHEMISTRY; RECEPTOR INTRINSIC ACTIVITY; SYNTHESIS; TRANSAMINATION;

EID: 0032729656     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199912)1999:12<3403::AID-EJOC3403>3.0.CO;2-U     Document Type: Article

References (18)

1. G. Johnson, Bioorg. Med. Chem. Lett. 1993, 3, 9.
2. F. C. Acher, F. J. Tellier, R. Azerad, I. N. Brabet, L. Fagui, P. R. J.-Pin, J. Med. Chem. 1997, 40, 3119-3129.
3. Z.-Q. Gu, P. Hesson, J. C. Pelletier, M.-L. Maccecchini, J. Med. Chem. 1995, 38, 2518-2520.
4. N. Todeschi, J. Gharbi-Benarous, F. Acher, V. Larue, J.-P. Pin, J. Bockaert, R. Azerad, J.-P. Girault, Bioorg. Med. Chem. 1997, 5, 335.
5. E. Coudert, F. Acher, R. Azerad, Synthesis 1997, 863; Z.-Q. Gu, D. P. Hesson, Tetrahedron: Asymmetry 1995, 6, 2101-2104.
6. E. Coudert, F. Acher, R. Azerad, Synthesis 1997, 863; Z.-Q. Gu, D. P. Hesson, Tetrahedron: Asymmetry 1995, 6, 2101-2104.
7. C. M. Moody, D. W. Young, Tetrahedron Lett. 1994, 35, 7277-7280.
8. A. Righini-Tapie, R. Azerad, J. Appl. Biochem. 1984, 6, 361-366.
9. F. Echalier, O. Constant, J. Bolte, J. Org. Chem. 1993, 58, 2747-2750.
10. E. E. Blaise, H. Gault, Bull. Soc. Chim. Fr. 1994, 458-464.
11. P. Dowd, S.-C. Choi, F. Duah, C. Kaufman, Tetrahedron 1988, 44, 2137-2148.
12. C.-S. Chen, Y. Fujimoto, G. Girdaukas, C. H. Sih, J. Am. Chem. Soc. 1982, 104, 7294-7299.
13. P. A. Fitzpatrick, A. M. Klibanov, J. Am. Chem. Soc. 1991, 113, 3166; F. Terradas, M. Teston-Henry, P. A. Fitzpatrick, A. M. Klibanov, J. Am. Chem. Soc. 1993, 115, 390.
14. P. A. Fitzpatrick, A. M. Klibanov, J. Am. Chem. Soc. 1991, 113, 3166; F. Terradas, M. Teston-Henry, P. A. Fitzpatrick, A. M. Klibanov, J. Am. Chem. Soc. 1993, 115, 390.
15. V. T. Pham, R. S. Phillips, L. G. Ljungdahl, J. Am. Chem. Soc. 1989, 111, 1935; R. S. Phillips, Trends Biotechnol. 1996, 14, 13; T. Sakai, T. Kishimoto, Y. Tanaka, T. Ema, M. Utaka, Tetrahedron Lett. 1998, 39, 7881-7884.
16. V. T. Pham, R. S. Phillips, L. G. Ljungdahl, J. Am. Chem. Soc. 1989, 111, 1935; R. S. Phillips, Trends Biotechnol. 1996, 14, 13; T. Sakai, T. Kishimoto, Y. Tanaka, T. Ema, M. Utaka, Tetrahedron Lett. 1998, 39, 7881-7884.
17. V. T. Pham, R. S. Phillips, L. G. Ljungdahl, J. Am. Chem. Soc. 1989, 111, 1935; R. S. Phillips, Trends Biotechnol. 1996, 14, 13; T. Sakai, T. Kishimoto, Y. Tanaka, T. Ema, M. Utaka, Tetrahedron Lett. 1998, 39, 7881-7884.
18. H. U. Bergmeyer, Methods of Enzymatic Analysis, 2nd ed. VCH, Weinheim, 1974, p 144 and 462.