Synthesis and conformational analysis of bicyclic extended dipeptide surrogates

Journal of Organic Chemistry

Volumn 75, Issue 15, 2010, Pages 5113-5125

  Ranatunga, Sujeewa ^a   Liyanage, Wathsala ^a   Del Valle, Juan R ^b  

^a NEW MEXICO STATE UNIVERSITY   (United States)

^b H LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLATIONS; AZIDATION; CONFORMATIONAL ANALYSIS; DI-PEPTIDES; DIASTEREOSELECTIVE REACTIONS; DIHEDRAL ANGLES; DIPEPTIDE; ENOLATES; MIMETICS; N-TERMINALS; PROLINE DERIVATIVES; PYROGLUTAMIC ACIDS; RING SIZES; STRUCTURAL DATA; TRIPEPTIDE;

CONFORMATIONS; SCAFFOLDS; STEREOCHEMISTRY; X RAY DIFFRACTION;

COMPLEXATION;

BETA LACTAM DERIVATIVE; CARBAMIC ACID DERIVATIVE; DIPEPTIDE DERIVATIVE; PYROGLUTAMIC ACID; PYRROLIZINE DERIVATIVE;

ARTICLE; BETA SHEET; DIASTEREOISOMER; MOLECULAR MIMICRY; MOLECULAR MODEL; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PROTEIN CONFORMATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

BICYCLO COMPOUNDS; DIPEPTIDES; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PROTEIN CONFORMATION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 77955149144     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1008433     Document Type: Article

References (56)

1. Somers, W. S.; Phillips, S. E. V. Nature 1992, 359, 387-393
2. Puglisi, J. D.; Chen, L.; Blanchard, S.; Frankel, A. D. Science 1995, 270, 1200-1203
3. Derrick, J. P.; Wigley, D. B. Nature 1992, 359, 752-754
4. Colon, W.; Kelly, J. W. Biochemistry 1992, 31, 8654-8660
5. Glenn, M. P.; Fairlie, D. P. Mini Rev. Med. Chem. 2002, 2, 433-445
6. Loughlin, W. A.; Tyndall, J. D. A.; Glenn, M. P.; Fairlie, D. P. Chem. Rev. 2004, 104, 6085-6118
7. Kemp, D. S.; Bowen, B. R.; Muendel, C. C. J. Org. Chem. 1990, 55, 4650-4657
8. Khakshoor, O.; Nowick, J. S. Curr. Opin. Chem. Biol. 2008, 12, 722-729
9. Levin, S.; Nowick, J. S. J. Am. Chem. Soc. 2007, 129, 13043-13048
10. Nowick, J. S. Acc. Chem. Res. 1999, 32, 287-296
11. Nowick, J. S.; Smith, E. M.; Noronha, G. J. Org. Chem. 1995, 60, 7386-7387
12. Nowick, J. S.; Cary, J. M.; Tsai, J. H. J. Am. Chem. Soc. 2001, 123, 5176-5180
13. Phillips, S. T.; Rezac, M.; Abel, U.; Kossenjans, M.; Bartlett, P. A. J. Am. Chem. Soc. 2002, 124, 58-66
14. Zeng, H.; Yang, X.; Flowers, R. A.; Gong, B. J. Am. Chem. Soc. 2002, 124, 2903-2910
15. Smith, C. K.; Regan, L. Acc. Chem. Res. 1997, 30, 153-161
16. Fairlie, D. P.; Tyndall, J. D. A.; Reid, R. C.; Wong, A. K.; Abbenante, G.; Scanlon, M. J.; March, D. R.; Bergman, D. A.; Chai, C. L. L.; Burkett, B. A. J. Med. Chem. 2000, 43, 1271-1281
17. Tyndall, J. D. A.; Fairlie, D. P. J. Mol. Recognit. 1999, 12, 363-370
18. Wolfram, B.; Robert, H. Eur. J. Biochem. 1992, 204, 433-451
19. Brown, J. H.; Jardetzky, T. S.; Gorga, J. C.; Stern, L. J.; Urban, R. G.; Strominger, J. L.; Wiley, D. C. Nature 1993, 364, 33-39
20. Sawyer, T. K.; Bohacek, R. S.; Dalgarno, D. C.; Eyermann, C. J.; Kawahata, N.; Metcalf, C. A.; Shakespeare, W. C.; Sundaramoorthi, R.; Wang, Y.; Yang, M. G. Mini-Rev. Med. Chem. 2002, 2, 475-488
21. Strickland, C. L.; Windsor, W. T.; Syto, R.; Wang, L.; Bond, R.; Wu, Z.; Schwartz, J.; Le, H. V.; Beese, L. S.; Weber, P. C. Biochemistry 1998, 37, 16601-16611
22. Long, S. B.; Casey, P. J.; Beese, L. S. Structure 2000, 8, 209-222
23. Yang, J.; Cron, P.; Good, V. M.; Thompson, V.; Hemmings, B. A.; Barford, D. Nat. Struct. Mol. Biol. 2002, 9, 940-944
24. Qian, Y.; Blaskovich, M. A.; Saleem, M.; Seong, C. M.; Wathen, S. P.; Hamilton, A. D.; Sebti, S. M. J. Biol. Chem. 1994, 269, 12410-12413
25. Clerc, F.-F.; Guitton, J.-D.; Fromage, N.; Lelièvre, Y.; Duchesne, M.; Tocqué, B.; James-Surcouf, E.; Commeron, A.; Becquart, J. Bioorg. Med. Chem. Lett. 1995, 5, 1779-1784
26. Qian, Y.; Marugan, J. J.; Fossum, R. D.; Vogt, A.; Sebti, S. M.; Hamilton, A. D. Bioorg. Med. Chem. 1999, 7, 3011-24
27. Kayser, K. J.; Glenn, M. P.; Sebti, S. M.; Cheng, J. Q.; Hamilton, A. D. Bioorg. Med. Chem. Lett. 2007, 17, 2068-73
28. Nowick, J. S.; Pairish, M.; Lee, I. Q.; Holmes, D. L.; Ziller, J. W. J. Am. Chem. Soc. 1997, 119, 5413-5424
29. Blomberg, D.; Brickmann, K.; Kihlberg, J. Tetrahedron 2006, 62, 10937-10944
30. Martin, S. F.; Austin, R. E.; Oalmann, C. J.; Baker, W. R.; Condon, S. L.; DeLara, E.; Rosenberg, S. H.; Spina, K. P.; Stein, H. H. J. Med. Chem. 1992, 35, 1710-1721
31. Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6568-6570
32. Burns, C. J.; Guitton, J.-D.; Baudoin, B.; Lelievre, Y.; Duchesne, M.; Parker, F.; Fromage, N.; Commercon, A. J. Med. Chem. 1997, 40, 1763-1767
33. Chandrasekhar, S.; Sudhakar, A.; Kiran, M. U.; Babu, B. N.; Jagadeesh, B. Tetrahedron Lett. 2008, 49, 7368-7371
34. Smith, A. B.; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947-9962
35. Angelo, N. G.; Arora, P. S. J. Am. Chem. Soc. 2005, 127, 17134-17135
36. Wyrembak, P. N.; Hamilton, A. D. J. Am. Chem. Soc. 2009, 131, 4566-4567
37. Gillespie, P.; Cicariello, J.; Olson, G. L. Peptide Sci. 1997, 43, 191-217
38. Hanessian, S.; McNaughtonSmith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854
39. Cluzeau, J.; Lubell, W. D. Peptide Sci. 2005, 80, 98-150
40. Halab, L.; Gosselin, F.; Lubell, W. D. Peptide Sci. 2000, 55, 101-122
41. Freidinger, R. M.; Perlow, D. S.; Veber, D. F. J. Org. Chem. 1982, 47, 104-109
42. Liyanage, W.; Weerasinghe, L.; Strong, R. K.; Del Valle, J. R. J. Org. Chem. 2008, 73, 7420-7423
43. Knight, D. W.; Share, A. C.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1997, 2089-2098
44. Hanessian, S.; Sharma, R. Heterocycles 2000, 52, 1231-1239
45. Yi, J. J.; Hua, Z. M.; Rong, T. G. Synth. Commun. 2003, 33, 3913-3917
46. Similar stereochemical outcomes were observed in the examples from ref 13.
47. Olofson, R. A.; Martz, J. T.; Senet, J. P.; Piteau, M.; Malfroot, T. J. Org. Chem. 1984, 49, 2081-2082
48. Olofson, R. A.; Schnur, R. C. Tetrahedron Lett. 1977, 18, 1571-1574
49. Use of excess trimethyltin hydroxide as a mild ester deprotection reagent gave only trace amounts of the desired acid. See: Nicolaou, K. C.; Estrada, A. A.; Zak, M.; Lee, S. H.; Safina, B. S. Angew. Chem., Int. Ed. 2005, 44, 1378-1382
50. The configurational instability of 12 and 16 versus 6c is likely due to steric interactions of the endo α′ substituent in the convex bicyclic frameworks. On the basis of the X-ray structure of 23, the ethylcarboxy substituent in 16 presumably also occupies an axial position.
51. For a study on similar reaction pathways with 1,1′- carbonyldiimidazole, see: de Figueiredo, R. M.; Fröhlich, R.; Christmann, M. J. Org. Chem. 2006, 71, 4147-4154
52. Venkatraman, J.; Shankaramma, S. C.; Balaram, P. Chem. Rev. 2001, 101, 3131-3152
53. It should be noted that these values are of roughly equal and opposite sign, which is the principle requirement for our surrogates. However, mimicry of a natural l, l -dipeptide strand would require the synthesis of the enantiomer scaffold starting from d -pyroglutamic acid.
54. Measured torsions and distances for 28 are given as the average between the two molecules in the dimer.
55. See Supporting Information for details.
56. See Experimental Section for details.