α-Amino-β-hydroxy-γ-lactam for constraining peptide Ser and Tnr residue conformation

Organic Letters

Volumn 12, Issue 8, 2010, Pages 1652-1655

  St Cyr, Daniel J ^a   Jamieson, Andrew G ^a   Lubell, William D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM; PEPTIDE; SERINE; THREONINE;

ARTICLE; CHEMISTRY; CONFORMATION;

LACTAMS; MOLECULAR CONFORMATION; PEPTIDES; SERINE; THREONINE;

EID: 77951182664     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1000582     Document Type: Article

References (50)

1. Glycosylation review: Steen, P. V. D.; Rudd, P. M.; Dwek, R. A.; Opdenakker, G. Crit. Rev. Biochem. Mol. Biol. 1998, 33, 151
2. Phosphorylation review: Pinna, L. A.; Ruzzene, M. Biochim. Biophys. Acta 1996, 1314, 191
3. Jenkins, C. L.; Bretsher, L. E.; Guzei, I. A.; Raines, R. T. J. Am. Chem. Soc. 2003, 125, 6422
4. Rao, M. H. V. R.; Pinyol, E.; Lubell, W. D. J. Org. Chem. 2007, 72, 736
5. For β-turns in 3-Hyp peptides: Chakraborty, T. K.; Srinivasu, P.; Rao, R. V.; Kumar, S. K.; Kunwar, A. C. J. Org. Chem. 2004, 69, 7399
6. For example, empedopeptin
7. 3: Wohlrab, A.; Lamer, R.; VanNieuwenhze, M. S. J. Am. Chem. Soc. 2007, 129, 4175
8. Cyclopeptide natural products review: Pomilio, A. B.; Battista, M. E.; Vitale, A. A. Curr. Org. Chem. 2006, 10, 2075
9. Toniolo, C. Int. J. Pept. Protein Res 1990, 35, 287 and references therein
10. Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Biopolymers 1997, 43, 219
11. An astute reviewer noted that the actual ground state conformation of the Figure 1 structures will likely be intermediate between the idealized Newman-projection staggered and eclipsed confomers due to the constraint of the five-membered ring.
12. Leeson, P. D.; Williams, B. J.; Rowley, M.; Moore, K. W.; Baker, R.; Kemp, J. A.; Priestley, T.; Foster, A. C.; Donald, A. E. Bioorg. Med. Chem. Lett. 1993, 3, 71
13. Okumura, K.; Inoue, K.; Fukamizu, M. Jpn. Patent 46041305 19711206, 1971.
14. Scholz, D.; Hecht, P.; Schmidt, H.; Billich, A. Monatsh. Chem. 1999, 130, 1283
15. Scholz, D.; Billich, A.; Charpiot, B.; Ettmayer, P.; Lehr, P.; Rosenwirth, B.; Schreiner, E.; Gstach, H. J. Med. Chem. 1994, 37, 3079
16. Alvarez-Ibarra, C.; Csãky, A. G.; Martínez-Santos, E.; Quiroga, M. L.; Tejedor, J. L. Tetrahedron 1999, 55, 3041
17. Limberg, G.; Lundt, I.; Zavilla, J. Synthesis 1999, 1, 178
18. Sauer, S.; Schumacher, A.; Barbosa, F.; Giese, B. Tetrahedron Lett. 1998, 39, 3685
19. Farran, D.; Toupet, L.; Martinez, J.; Dewynter, G. Org. Lett. 2007, 9, 4833
20. Leban, J. J.; Colson, K. L. J. Org. Chem. 1996, 61, 228
21. Almeida, J. F.; Grande, M.; Moran, J. R.; Anaya, J.; Mussons, L.; Caballero, C. Tetrahedron: Asymmetry 1993, 4, 2483
22. Cottrell, I. F.; Davis, P. J.; Moloney, M. G. Tetrahedron: Asymmetry 2004, 15, 1239
23. Jamieson, A. G.; Boutard, N.; Beauregard, K.; Bodas, M. S.; Ong, H.; Quiniou, C.; Chemtob, S.; Lubell, W. D. J. Am. Chem. Soc. 2009, 131, 7917
24. Boutard, N.; Jamieson, A. G.; Ong, H.; Lubell, W. D. Chem. Biol. Drug Des. 2010, 75, 40
25. Truong, T. V.; Rapoport, H. J. Org. Chem. 1993, 58, 6090
26. Shaw, K. J.; Luly, J. R.; Rapoport, H. J. Org. Chem. 1985, 50, 4515
27. N -(Fmoc)vinylglycine-OMe precursor
28. Organ, M. G.; Xu, J.; N'Zemba, B. Tetrahedron Lett. 2002, 43, 8177
29. Vinylglycine synthesis
30. Afzali-Ardakani, A.; Rapoport, H. J. Org. Chem. 1980, 45, 4817
31. Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H. Org. Synth. 1992, 70, 29
32. Meffre, P.; Vo-Quang, L.; Vo-Quang, Y.; Le Goffic, F. Synth. Commun. 1989, 19, 3457
33. Review: Berkowitz, D. B.; Charette, B. D.; Karukurichi, K. R.; McFadden, J. M. Tetrahedron: Asymmetry 2006, 17, 869.
34. The enantiomeric purity of 3 was ascertained by chiral SFC chromatography to be of >96%. The major diasteriomer was assigned by conversion of (2 S,2- S)- N -(Cbz)oxiranylglycine methyl ester into 3 under hydrogenative conditions
35. Dzubeck, V.; Schneider, J. P. Tetrahedron Lett. 2000, 41, 9953
36. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923
37. See the Supporting Information for details.
38. 2NOBn and Gly; see ref 9a and: Tashiro, T.; Fushiya, S.; Nozoe, S. Chem. Pharm. Bull. 1988, 36, 893
39. 2O, 46%.
40. Philippe, C.; Milcent, T.; Crousse, B.; Bonnet-Delpon, D. Org. Biomol. Chem. 2009, 7, 2026
41. Das, U.; Crousse, B.; Kesavan, V.; Bonnet-Delpon, D.; Bégué, J.-P. J. Org. Chem. 2000, 65, 6749
42. Westermaier, M.; Mayr, H. Chem. - Eur. J. 2008, 14, 1638
43. Review: Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Synlett 2004, 1, 18
44. (2 S,2-S)- N -(Cbz)oxiranylglycine methyl ester β-eliminated to afford 3-(Cbz-amino)furan-2(5 H)-one. (12) Reversible β-elimination may explain racemization.
45. Galaud, F.; Demers, A.; Ong, H.; Lubell, W. D., Understanding Biology Using Peptides; Blondelle, S. E., Ed.; Springer: New York, 2006; pp 188-189.
46. Quiniou, C.; Sapieha, P.; Lahaie, I.; Hou, X.; Brault, S.; Beauchamp, M.; Leduc, M.; Rihakova, L.; Joyal, J.-S.; Nadeau, S.; Heveker, N.; Lubell, W. D.; Sennlaub, F.; Gobeil, F., Jr.; Miller, G.; Pshezhetsky, A. V.; Chemtob, S. J. Immunol. 2008, 180, 6977
47. Chemtob, S.; Quiniou, C.; Lubell, W. D.; Beauchamp, M.; Hansford, K. A. US Patent No. 20,060-094,663, 2006.
48. Quiniou, C.; Kooli, E.; Joyal, J.-S.; Sapieha, P.; Sennlaub, F.; Lahaie, I.; Zhuo, S.; Hou, X.; Hardy, P.; Lubell, W.; Chemtob, S. Semin. Perinatol. 2008, 32, 325
49. Fields, G. B.; Noble, R. L. Int. J. Pept. Protein Res. 1990, 35, 161
50. Lubell, W. D.; Blankenship, J. W.; Fridkin, G.; Kaul, R. 21.11 Peptides. In Science of Synthesis, Volume 21: Three Carbon-Heteroatom Bonds: Amides and Derivatives; Peptides; Lactams; Weinreb, S. M., Ed.; Thieme: Stuttgart, 2005.