Proline editing: A divergent strategy for the synthesis of conformationally diverse peptides

Organic Letters

Volumn 7, Issue 12, 2005, Pages 2397-2400

  Thomas, Krista M ^a   Naduthambi, Devan ^a   Tririya, Gasirat ^a   Zondlo, Neal J ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; PEPTIDE DERIVATIVE; PROLINE DERIVATIVE;

ARTICLE; PEPTIDE SYNTHESIS; PROTEIN CONFORMATION; STATISTICAL SIGNIFICANCE; SUBSTITUTION REACTION;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; PROLINE; PROTEIN CONFORMATION;

EID: 20544453286     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0506720     Document Type: Article

References (50)

1. (a) Fairlie, D. P.; West, M. L.; Wong, A. K. Curr. Med. Chem. 1998, 5, 29-62.
2. (b) Peczuh, M. W.; Hamilton, A. D. Chem. Rev. 2000, 100, 2479-2493.
3. (c) Venkatraman, J.; Shankaramma, S. C.; Balaram, P. Chem. Rev. 2001, 101, 3131-3152.
4. (d) Cowell, S. M.; Lee, Y. S.; Cain, J. P.; Hruby, V. J. Curr. Med. Chem. 2004, 11, 2785-2798.
5. (a) Kay, B. K.; Williamson, M. P.; Sudol, P. FASEB J. 2000, 14, 231-241.
6. (b) Reiersen, H.; Rees, A. R. Trends Biochem. Sci. 2001, 26, 679-684.
7. (a) Panasik, N.; Eberhardt, E. S.; Edison, A. S.; Powell, D. R.; Raines, R. T. Int. J. Pept. Protein Res. 1994, 44, 262-269.
8. (b) Eberhardt, E. S.; Panasik, N., Jr.; Raines, R. T. J. Am. Chem. Soc. 1996, 118, 12261-12266.
9. (c) Holmgren, S. K.; Taylor, K. M.; Bretscher, L. E.; Raines, R. T. Nature 1998, 392, 666-667.
10. (d) Holmgren, S. K.; Bretscher, L. E.; Taylor, K. M.; Raines, R. T. Chem. Biol. 1999, 6, 62-70.
11. (e) Bretscher, L. E.; Jenkins, C. L.; Taylor, K. M.; DeRider, M. L.; Raines, R. T. J. Am. Chem. Soc. 2001, 123, 777-778.
12. (f) Jenkins, C. L.; Raines, R. T. Nat. Prod. Rep. 2002, 19, 49-59.
13. (g) DeRider, M. L.; Wilkens, S. J.; Waddell, M. J.; Bretscher, L. E.; Weinhold, F.; Raines, R. T.; Markley, J. L. J. Am. Chem. Soc. 2002, 124, 2497-2505.
14. (h) Hodges, J. A.; Raines, R. T. J. Am. Chem. Soc. 2003, 125, 9262-9263.
15. (i) Jenkins, C. L.; McCloskey, A. I.; Guzei, I. A.; Eberhardt, E. S.; Raines, R. T. Biopolymers 2005, 80, 1-8.
16. (a) Gerig, J. T.; McLeod, R. S. J. Am. Chem. Soc. 1973, 95, 5725-5729.
17. (b) Renner, C.; Alefelder, S.; Bae, J. H.; Budisa, N.; Huber, R.; Moroder, L. Angew. Chem., Int. Ed. 2001, 40, 923-925.
18. (c) Dugave, C.; Demange, L. Chem. Rev. 2003, 103, 2475-2532.
19. (d) Taylor, C. M.; Hardre, R.; Edwards, P. J. B. J. Org. Chem. 2005, 70, 1306-1315.
20. (a) Babu, I. R.; Ganesh, K. N. J. Am. Chem. Soc. 2001, 123, 2079-2080.
21. (b) Malkar, N. D.; Lauer-Fields, J. L.; Borgia, J. A.; Fields, G. B. Biochemistry 2002, 41, 6054-6064.
22. (c) Doi, M.; Nishi, Y.; Uchiyama, S.; Nishiuchi, Y.; Nakazawa, T.; Ohkubo, T.; Kobayashi, Y. J. Am. Chem. Soc. 2003, 125, 9922-9923.
23. (d) Persikov, A. V.; Ramshaw, J. A. M.; Kirkpatrick, A.; Brodsky, B. J. Am. Chem. Soc. 2003, 125, 11500-11501.
24. (e) Barth, D.; Milbrandt, A. G.; Renner, C.; Moroder, L. ChemBioChem 2004, 5, 79-86.
25. (f) Berisio, R.; Granata, V.; Vitagliano, L.; Zagari, A. J. Am. Chem. Soc. 2004, 126, 11402-11403.
26. Kim, W. Y.; George, A.; Evans, M.; Conticello, V. P. Chembiochem 2004, 5, 928-936.
27. (a) An, S. S. A.; Lester, C. C.; Peng, J.-L.; Li, Y.-J.; Rothwarf, D. M.; Welker, E.; Thannhauser, T. W.; Zhang, L. S.; Tam, J. P.; Scheraga, H. A. J. Am. Chem. Soc. 1999, 121, 11558-11566.
28. (b) Keller, M.; Sager, C.; Dumy, P.; Schutkowski, M.; Fischer, G. S.; Mutter, M. J. Am. Chem. Soc. 1998, 120, 2714-2720.
29. (c) Halab, L.; Lubell, W. D. J. Am. Chem. Soc. 2002, 124, 2474-2484.
30. (d) Delaney, N. G.; Madison, V J. Am. Chem. Soc. 1982, 104, 6635-6641.
31. (a) Schmid, F. X. Adv. Protein Chem. 2002, 59, 243-282.
32. (b) Andreotti, A. H. Biochemistry 2003, 42, 9515-9524.
33. (a) Demange, L.; Ménez, A.; Dugave, C. Tetrahedron Lett. 1998, 39, 1169-1172.
34. (b) Doi, M.; Nishi, Y.; Kiritoshi, N.; Iwata, T.; Nago, M.; Nakano, H.; Uchiyama, S.; Nakazawa, T.; Wakamiya, T.; Kobayashi, Y. Tetrahedron 2002, 58, 8453-8459.
35. 2Pro, or Boc-4-oxo-Pro.
36. For example, the synthesis of a 20 residue peptide in which residue 11 is varied to incorporate each 4-substituted proline derivative described herein would require 7 x 11 = 77 amide coupling cycles (with each cycle including deprotection, coupling, and wash steps) after the resin split via standard methodology, versus 11 amide coupling cycles using proline editing, a significant reduction in required time and material resources. In addition, only seven manual on-resin reactions, in total, are required to prepare all seven derivatives (Scheme 2), versus 27 solution-phase synthetic steps to prepare the required Fmoc amino acids from trans-hydroxyproline methyl ester.
37. O'Donnell, M. J.; Zhou, C. Y.; Scott, W. L. J. Am. Chem. Soc. 1996, 118, 6070-6071.
38. (a) Grathwohl, C.; Wüthrich, K. Biopolymers 1976, 15, 2025-2041.
39. (b) Grathwohl, C.; Wüthrich, K. Biopolymers 1981, 20, 2623-2633.
40. (c) Yao, J.; Dyson, H. J.; Wright, P. E. J. Mol. Biol. 1994, 243, 754-766.
41. (d) Hutchinson, E. G.; Thornton, J. M. Protein Sci. 1994, 3, 2207-2216.
42. (e) Wu, W.-J.; Raleigh, D. P. Biopolymers 1998, 45, 381-394.
43. (f) Reimer, U.; Scherer, G.; Drewello, M.; Kruber, S.; Schutkowski, M.; Fischer, G. J. Mol. Biol. 1998, 279, 449-460.
44. (g) Pal, D.; Chakrabarti, P. J. Mol. Biol. 1999, 294, 271-288.
45. 12d
46. Acetylation of the hydroxyl group was alternatively used as an effective orthogonal hydroxyl side chain protection strategy. See Supporting Information for details.
47. Melnyk, O.; Fehrentz, J. A.; Martinez, J.; Gras-Masse, H. Biopolymers 2000, 55, 165-186.
48. (a) Vergnon, A. L.; Pottorf, R. S.; Player, M. R. J. Comb. Chem. 2004, 6, 91-98.
49. (b) Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017-3020.
50. Vuister, G. W.; Bax, A. J. Am. Chem. Soc. 1993, 115, 7772-7777.