Chemo-enzymatic synthesis of the four stereoisomers of 4-hydroxy-4- methylglutamic acid

Tetrahedron Asymmetry

Volumn 9, Issue 21, 1998, Pages 3855-3861

  Helaine, Virgil ^a   Bolte, Jean ^a  

^a LASMEA Universite Blake Pascal   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXY 4 METHYLGLUTAMIC ACID DERIVATIVE; GLUTAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

EID: 0032491617     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00372-3     Document Type: Article

References (24)

1. Monaghan, D. T.; Bridges, R. J.; Cotman, C. W. Ann. Rev. Pharmacol. Toxicol. 1989, 29, 365-402.
2. Siegelbaum, S. A.; Kandel, E. R. Curr. Opin. Neurobiol. 1991, 1, 113-120.
3. (a) Olney, J. W. Ann. Rev. Pharmacol. Toxicol. 1990, 30, 47-71.
4. (b) Meldrum, B. Brain Res. Rev. 1993, 18, 293-314.
5. (a) Nakanishi, S. Science 1992, 258, 597-603.
6. (b) Cunningham, M. O.; Ferkany, J. W.; Enna. S. J. Life Sci. 1993, 54, 135-148.
7. Acher, F. C.; Tellier, F. J.; Azerad, R.; Brabet, I. N.; Fagny, L.; Pin, J.-P. R. J. Med. Chem. 1997, 40, 3119-3129.
8. (a) Gu, Z.-Q.; Hesson, D. P.; Pelletier, J. C.; Maccaecchini, M.-L. J. Med. Chem. 1995, 38, 2518-2519.
9. (b) Todeshi, N.; Gharbi-Benarous, J.; Acher, F.; Larue, V.; Pin, J.-P.; Bockaert, J.; Azerad, R.; Girault, J.-P. Bioorg. Med. Chem. 1997, 5, 335.
10. (a) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277-7280.
11. (b) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1993, 34, 4667-4670.
12. (c) Coudert, E.; Acher, F.; Azerad, R. Tetrahedron: Asymmetry 1994, 5, 731.
13. (d) Gu, Z.-Q.; Hesson, D. P. Tetrahedron: Asymmetry 1995, 6, 2101.
14. (a) Passerat, N.; Bolte, J. Tetrahedron Lett. 1987, 28, 1277-1280.
15. (b) Echalier, F.; Constant, O.; Bolte, J. J. Org. Chem. 1993, 58, 2747-2750.
16. Jadot, J.; Casimir, J.; Loffet, A. Biochim. Biophys. Acta 1967, 136, 79-88.
17. Alderweireldt, F.; Jadot, J.; Casimir, J.; Loffet, A. Biochim. Biophys. Acta 1967, 136, 89-94.
18. Meier, L. K.; Sorensen, J. Phytochemistry 1979, 18, 1173-1175.
19. Olsen, O.; Sorensen, H. Phytochemistry 1980, 19, 1717-1721.
20. Yang, S.; Hayden, W.; Faber, K.; Griengl, H. Synthesis 1992, 365.
21. (b) Yang, S.; Hayden, W.; Faber, K.; Griengl, H. Monatsschr. Chemie 1994, 125, 469-477.
22. Kaas, K.; Sorensen, H. Acta Chem. Scand. A 1977, 31, 364-368.
23. Tripos Associates, Inc., 1969 S. Harley Rd., Suite 303, St Louis, MO 63144, USA.
24. Merz, K. M.; Besler, B. H. MOPAC version 5.0 ESC, QCPE no. 589, 1990, with AM1 force field parameters.