Resolution and regioselective protection of glutamic acid analogues. II - Synthesis, resolution and configuration assignment of (+)-α-methyl-4-carboxyphenylglycine (M4CPG)

Tetrahedron Asymmetry

Volumn 7, Issue 10, 1996, Pages 2963-2970

  Coudert, Elisabeth ^a   Acher, Francine ^a   Azerad, Robert ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA METHYL 4 CARBOXYPHENYLGLYCINE; DIPEPTIDE; GLYCINE DERIVATIVE; LEUCYL(ALPHA METHYL 4 CARBOXYPHENYLGLYCINE); UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN PURIFICATION; TECHNIQUE; X RAY CRYSTALLOGRAPHY;

EID: 0030271721     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00387-4     Document Type: Article

References (47)

1. 1. Pin, J-P.; Duvoisin, R. Neuropharmacology 1995, 54, 1-26.
2. 2. Watkins, J.; Collingridge, G. Trends Pharmacol Sci. 1994, 15, 333-342.
3. 3. Roberts, P.J. Neuropharmacology 1995, 34, 813-819.
4. 4. Sekijama, N.; Hayashi, Y.; Nakanishi, S.; Jane, D.E.; Tsee, H.-W.; Birse, E.F. & Watkins, J.C. Br. J. Pharmacol. 1994, 117, 1493-1503.
5. 5. Jane, D.E.; Jones, P.L. St J.; Pook, P.C.K.; Salt, T.E.; Sunter, D.C.; Watkins, J.C. Neuropharmacology 1993, 32, 725-727.
6. 6. a) Eaton, S.A.; Jane, D.E.; Jones, P.L. St J.; Porter, R.H.P.; Pook, P.C.K.; Sunter D.C.; Udvarhelyi, P.M.; Roberts, P.J.; Salt, T.E.; Watkins, J.C. Eur. J. Pharmacol. Mol. Pharmacol. 1993, 244, 195-197.
7. b) Glaum, S.R.; Sunter, D.C.; Udvarhelyi, P.M.; Watkins, J.C.; Miller, R.J. Neuropharmacology 1993, 32 , 1419-1425.
8. c) Lingenhöhl, K.; Olpe, H.R.; Bendali, N.; Knöpfel, T. Neurosci. Res. 1993, 18, 229-234.
9. d) Kemp, M.; Roberts, P.J.; Pook, P.C.K.; Jane, D.E.; Jones, A.; Jones, P.; Sunter, D.C.; Udvarhelyi, P.M.; Watkins, J.C. Eur. J. Pharmacol Mol. Pharmacol. 1994, 266, 187-192.
10. e) Thomsen, C.; Boel, E.; Suzdak, P.D. Eur. J. Pharmacol. Mol. Pharmacol. 1994, 267, 77-84.
11. f) Hayashi, Y.; Sekiyama, N.; Nakanishi, S.; Jane, D.E.; Sunter, D.C.; Birse, E.F.; Udvarhelyi, P.M.; Watkins, J.C. J. Neurosci. 1994, 14, 3370-3377.
12. 7. a) Pelliciari, R.; Luneia, R.; Constantino, G.; Marinozzi, M.; Natalini, B.; Jakobsen P.; Kanstrup, A.; Lombardi, G.; Moroni, F. and Thomsen, C. J. Med. Chem. 1995, 38, 3717-3719.
13. b) Tellier, F.; Acher, F.C.; Brabet, I.; Pin, J.-P.; Bockaert, J. and Azerad, R. Bioorg. & Med. Chem. Lett. 1995, 5, 2627-2632.
14. c) Annoura, H.; Fukunaga, A.; Uesugi, M. Bioorg. & Med. Chem. Lett. 1996, 6, 763-66.
15. 8. a) Jane, D.E.; Jones, P.L. St. J.; Pook, P.-K.; Tse, H.-W & Watkins, J.C. Br. J. Pharmacol. 1994, 112, 809-816.
16. b) Wermuth, C.G.; Mann, A.; Schoenfelder, A.; Wright, R.; Johnson, B.G.; Burnett, J.P.; Mayne, N.G. and Schoepp, D. J. Med. Chem. 1996, 39, 814-816.
17. c) Pelliciari, R.; Marinozzi, M.; Natalini, B.; Constantino, G.; Luneia, R.; Giorgi, G.; Moroni, F.; Thomsen, C. J. Med. Chem. 1996, 39, 2259-2269.
18. 9. a) Williams, R.M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989.
19. b) Duthaler, R.O. Tetrahedron 1994, 50, 1539-1650.
20. 10. Goodson, L.H.; Honigberg, I.L.; Lehman, J.J.; Burton, W.H. J. Org. Chem. 1990, 25, 1920-1924.
21. 11. a) Chang, S.-C.; Charles, R; Gil-Av, E. J. Chromatogr. 1982, 238, 29-39.
22. b) Weinstein, S.; Grinberg, N. J. Chromatogr. 1985, 318, 117-121.
23. c) Keller, J.W.; Dick, K.O. J. Chromatogr. 1986, 367, 187-190.
24. d) Brükner, H. Chromatographia 1987, 24, 725-737.
25. e) Maurs, M.; Trigalo, F.; Azerad, R. J. Chromatogr. 1988, 440, 209-215.
26. f) Brükner, H.; Kühne, S; Zivny, S.; Langer, M.; Zaminski, Z.J.; Leplawy, M.T. in Second Forum on Peptides, Aubry, A.; Marraud, M.; Vitoux, B. ed.; Colloques INSERM/John Libbey Eurotext Ltd: Paris, 1989, pp. 291-295.
27. g) Duchateau, A.L.L.; Knuts, H.; Boesten, J.M.M.; Guns, J.J. J. Chromatogr. 1992, 623, 237-245.
28. h) Zhao, M.X.; Bada, J.L. J. Chromatogr. A 1995, 690, 55-63.
29. 12. Udvarhelyi, P.M.; Watkins, J.C. Chirality 1990, 2, 200-204.
30. 13. a) Macaudière, P.; Lienne, M.; Tambuté, A.; Caude, M. in Chiral Separations by HPLC; Krstulovic, A.M. ed.; Ellis Horwood Ltd: Chichester, U.K., 1989; pp. 399-445.
31. b) Dernoncour, R.; Azerad, R. J. Chromatogr. 1987, 470, 335-361.
32. 14. a) Brückner, H; Keller-Hoehl, C.; Godel, H.; Winner, R. Peptides 1990, 334-336.
33. b) Calmes, M.; Daunis, J.; Hanouneh, A.; Jacquier, R. Tetrahedron: Asymmetry 1993, 4, 2437-2440.
34. 15. Maurs, M.; Ducrocq, C.; Righini-Tapie, A.; Azerad, R. J. Chromatogr. 1985, 325, 444-449.
35. 16. Mosandl, A.; Gessner, M.; Günther, C.; Deger, W.; Singer G. J. High Resol. Chromatogr. & Chromatogr. Commun. 1987, 10, 67-70.
36. 17. Davankov, V.A. in Chiral Separations by HPLC; Krstulovic, A.M. ed.; Ellis Horwood Ltd: Chichester, U.K., 1989; pp. 446-475.
37. 18. The use of the Chiralpak MA(+) column (Daicel) was suggested by J.T. Baker Laboratories. Other α,α-dialkyl amino acids are also quite satisfactorily resolved on that specific column (unpublished results).
38. 19. Acher, F.; Azerad R. Tetrahedron: Asymmetry 1994, 5, 731-744.
39. 20. a) Trigalo, F.; Acher, F.; Azerad, R. Tetrahedron 1990, 46, 5203-5212.
40. b) Mitchell, A.R.; Kent, S.B.H.; Chu, I.C.; Merrifield, R.B. Anal. Chem. 1978, 50, 637-640.
41. 21. Frérot, E.; Coste, J.; Pantaloni, A.; Dufour, M.-N.; Jouin P. Tetrahedron 1991, 47, 259-270.
42. 22. a) Bambino, F; Brownlee, R.T.C.; Chiu, F.C.K. Tetrahedron Lett. 1991, 32, 3407-3409.
43. b) Brunissen, A.; Ayoub, M.; Lavielle, S. Tetrahedron Lett. 1996, submitted for publication.
44. 23. Rodriguez, M.; Aumelas, A.; Martinez, J. Tetrahedron Lett. 1990, 31, 5153-5156.
45. 24. We have been recently informed that the same assignment has been simultaneously made by D.E. Jane and should be soon reported (D.C. Sunter, personal communication).
46. 25. Von Arx, E.; Faupel, M.; Brugger, M. J. Chromatogr. 1976, 120, 224-228.
47. 26. Full details of the structure determination have been deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, CB2 1EZ, Cambridge, UK.