Synthesis of enantiopure, axially chiral, Cα-tetrasubstituted α-amino acids with binaphthyl-based crowned side chains and 3D-structural analysis of their peptides

Tetrahedron

Volumn 64, Issue 10, 2008, Pages 2307-2320

  Wright, Karen ^a   Lohier, Jean François ^a   Wakselman, Michel ^a   Mazaleyrat, Jean Paul ^a   Formaggio, Fernando ^b   Peggion, Cristina ^b   De Zotti, Marta ^b   Toniolo, Claudio ^b  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

^b CNR   (Italy)

Author keywords

Atropoisomerism; Binaphthyl; Biphenyl; C Tetrasubstituted amino acids; Crowned amino acids; Infrared absorption; NMR; Peptide conformation

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; AMINO ACID DERIVATIVE; BIPHENYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; HYDROXYL GROUP; NAPHTHYL GROUP; PEPTIDE DERIVATIVE; PHENOL;

ALKYLATION; AMINO ACID SYNTHESIS; ARTICLE; CHIRALITY; CYCLIZATION; ENANTIOMER; INFRARED SPECTROSCOPY; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTEIN SECONDARY STRUCTURE; PROTEIN STRUCTURE; STRUCTURE ANALYSIS;

EID: 38949099708     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.019     Document Type: Article

References (69)

1. Berthet M., and Sonveaux E. Biopolymers 25 (1986) 189-204
2. Voyer N., and Roby J. Tetrahedron Lett. 32 (1991) 331-334
3. Voyer N. J. Am. Chem. Soc. 113 (1991) 1818-1821
4. Voyer N., Deschênes D., Bernier J., and Roby J. J. Chem. Soc., Chem. Commun. (1992) 134-136
5. Voyer N., and Lamothe J. Tetrahedron 51 (1995) 9241-9284
6. Voyer N., Roby J., Deschênes D., and Bernier J. Supramol. Chem. 5 (1995) 61-69
7. Voyer N. Topics in Current Chemistry Vol. 184 (1996), Springer, Berlin pp 1-37
8. Voyer N., and Guérin B. Chem. Commun. (1997) 2329-2330
9. Voyer N., Potvin L., and Rousseau E. J. Chem. Soc., Perkin Trans. 2 (1997) 1469-1471
10. Meillon J.-C., and Voyer N. Angew. Chem. 109 (1997) 1004-1006
11. Angew. Chem., Int. Ed. 36 (1997) 967-969
12. Biron E., Voyer N., Meillon J.-C., Cormier M.-E., and Auger M. Biopolymers 55 (2000) 364-372
13. Meillon J.-C., Voyer N., Biron E., Sanschagrin F., and Stoddart J.F. Angew. Chem. 112 (2000) 147-149
14. Angew. Chem., Int. Ed. 39 (2000) 143-145
15. Vandenburg Y.R., Smith B.D., Biron E., and Voyer N. Chem. Commun. (2002) 1694-1695
16. Biron E., Otis F., Meillon J.-C., Robitaille M., Lamothe J., Van Hove P., Cormier M.-E., and Voyer N. Bioorg. Med. Chem. 12 (2004) 1279-1290
17. Tremblay M., Côté S., and Voyer N. Tetrahedron 61 (2005) 6824-6828
18. Otis F., Voyer N., Polidori A., and Pucci B. New J. Chem. 30 (2006) 185-190
19. Ouellet M., Otis F., Voyer N., and Auger M. Biochim. Biophys. Acta 1758 (2006) 1235-1244
20. Ouellet M., Doucet J.-D., Voyer N., and Auger M. Biochemistry 46 (2007) 6597-6606
21. Boudreault P.-L., and Voyer N. Org. Biomol. Chem. 5 (2007) 1459-1465
22. Voyer N., and Guérin B. Tetrahedron 50 (1994) 989-1010
23. Anzai J., Ueno A., and Osa T. Makromol. Chem., Rapid Commun. 3 (1982) 55-58
24. Toniolo C., Crisma M., Formaggio F., Peggion E., Broxterman Q.B., and Kaptein B. Biopolymers (Pept. Sci.) 76 (2004) 162-176
25. Toniolo C., Crisma M., Formaggio F., Peggion C., Broxterman Q.B., and Kaptein B. J. Inclusion Phenom. Macrocyclic Chem. 51 (2005) 121-136
26. Marshall G.R. In: Kharasch N. (Ed). Intrascience Chemistry Report (1971), Gordon and Breach, New York, NY 305-316
27. Karle I.L., and Balaram P. Biochemistry 29 (1990) 6747-6756
28. Toniolo C., and Benedetti E. Trends Biochem. Sci. 16 (1991) 350-353
29. Toniolo C., and Benedetti E. Macromolecules 24 (1991) 4004-4009
30. Toniolo C., Formaggio F., Kaptein B., and Broxterman Q.B. Synlett (2006) 1295-1310
31. Toniolo C., Crisma M., Formaggio F., Valle G., Cavicchioni G., Précigoux G., Aubry A., and Kamphuis J. Biopolymers 33 (1993) 1061-1072
32. Toniolo C., Crisma M., Formaggio F., and Peggion C. Biopolymers (Pept. Sci.) 60 (2001) 396-419
33. Karle I.L. Biopolymers 40 (1996) 157-180
34. Karle I.L. Acc. Chem. Res. 32 (1999) 693-701
35. Bolin K.A., and Millhauser G.L. Acc. Chem. Res. 32 (1999) 1027-1033
36. Mazaleyrat J.P., Gaucher A., Goubard Y., Šavrda J., and Wakselman M. Tetrahedron Lett. 38 (1997) 2091-2094
37. Mazaleyrat J.-P., Goubard Y., Azzini M.-V., Wakselman M., Crisma M., Formaggio F., and Toniolo C. In: Martinez J., and Fehrentz J.-A. (Eds). Peptides 2000 (2001), EDK, Paris, France 185-186
38. Mazaleyrat J.-P., Goubard Y., Azzini M.-V., Wakselman M., Peggion C., Formaggio F., and Toniolo C. Eur. J. Org. Chem. (2002) 1232-1247
39. Wright K., Melandri F., Cannizzo C., Wakselman M., and Mazaleyrat J.-P. Tetrahedron 58 (2002) 5811-5820
40. Formaggio F., Oancea S., Peggion C., Crisma M., Toniolo C., Wright K., Wakselman M., and Mazaleyrat J.-P. Biopolymers (Pept. Sci.) 71 (2003) 667-674
41. Wright, K.; Anddad, R.; Lohier, J.-F.; Steinmetz, V.; Wakselman, M.; Mazaleyrat, J.-P.; Formaggio, F.; Peggion, C.; De Zotti, M.; Keiderling, T. A.; Huang, R.; Toniolo, C. Eur. J. Org. Chem., in press. doi:10.1002/ejoc.200700917
42. Kotha S., and Brahmachary E. J. Org. Chem. 65 (2000) 1359-1365
43. Bělohradský M., Císařová I., Holý P., Pastor J., and Závada J. Tetrahedron 58 (2002) 8811-8823
44. Bělohradský M., Buděšínský M., Císařová I., Dekoj V., Holý P., and Závada J. Tetrahedron 59 (2003) 7751-7760
45. Cram D.J., and Cram J.M. Science 183 (1974) 803-809
46. Cram D.J., and Cram J.M. Acc. Chem. Res. 11 (1978) 8-14
47. Cram D.J. Angew. Chem., Int. Ed. Engl. 27 (1988) 1009-1020
48. Angew. Chem. 100 (1988) 1041-1052
49. Kyba E.P., Gokel G.W., de Jong F., Koga K., Sousa L.R., Siegel M.G., Kaplan L., Sogah G.D.Y., and Cram D.J. J. Org. Chem. 42 (1977) 4173-4184
50. A preliminary report of part of this work has been already published:. Mazaleyrat J.-P., Wright K., Azzini M.-V., Gaucher A., and Wakselman M. Tetrahedron Lett. 44 (2003) 1741-1745
51. Felix A.M. J. Org. Chem. 39 (1974) 1427-1429
52. Dale J.A., Dull D.L., and Mosher H.S. J. Org. Chem. 34 (1969) 2543-2549
53. Fuller W.D., Cohen M.P., Shabankareh M., Blair R.K., Goodman M., and Naider F.R. J. Am. Chem. Soc. 112 (1990) 7414-7416
54. Fuller W.D., Goodman M., Naider F.R., and Zhu Y.-F. Biopolymers 40 (1996) 183-205
55. Carpino L.A., Imazumi H., El-Faham A., Ferrer F.J., Zhang C., Lee Y., Foxman B.M., Henklein P., Hanay C., Mügge C., Wenschuh H., Klose J., Beyermann M., and Bienert M. Angew. Chem., Int. Ed. 41 (2002) 441-445
56. Angew. Chem. 114 (2002) 457-4651
57. Carpino L.A. J. Am. Chem. Soc. 115 (1993) 4397-4398
58. Cung M.T., Marraud M., and Néel J. Ann. Chim. Fr. 7 (1972) 183-209
59. Bonora G.M., Mapelli C., Toniolo C., Wilkening R.R., and Stevens E.S. Int. J. Biol. Macromol. 6 (1984) 179-188
60. Bellamy L.J. The Infrared Spectra of Complex Molecules (1966), Methuen, London
61. Wüthrich K. NMR of Proteins and Nucleic Acids (1986), Wiley, New York, NY
62. Jarvo E.R., and Miller S.J. Tetrahedron 58 (2002) 2481-2495
63. Miller S.J. Acc. Chem. Res. 37 (2004) 601-610
64. Cram D.J., and Sogah D.Y. J. Chem. Soc., Chem. Commun. (1981) 625-628
65. Cram D.J., and Sogah D.Y. J. Am. Chem. Soc. 107 (1985) 8301-8302
66. Brunet E., Poveda A.M., Rabasco D., Oreja E., Font L.M., Batra M.S., and Rodriguez-Ubis J.C. Tetrahedron: Asymmetry 5 (1994) 935-948
67. To{combining double acute accent}ke L., Bakó P., Keserü G., Albert M., and Fenichel L. Tetrahedron 54 (1998) 213-222
68. Krause N., and Hoffmann-Röder A. Synthesis (2001) 171-196
69. Bakó T., Bakó P., Keglevich G., Báthori N., Czugler M., Tatai J., Novák T., Parlagh G., and To{combining double acute accent}ke L. Tetrahedron: Asymmetry 14 (2003) 1917-1923