Building functionalized peptidomimetics: Use of electroauxiliaries for introducing N-acyliminium ions into peptides

Journal of the American Chemical Society

Volumn 128, Issue 42, 2006, Pages 13761-13771

  Sun, Haizhou ^a   Martin, Connor ^a   Kesselring, David ^a   Keller, Rebecca ^a   Moeller, Kevin D ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCHEMISTRY; ELECTRONS; IONS; NITROGEN COMPOUNDS; OXIDATION; SYNTHESIS (CHEMICAL);

ACYLIMINIUM; ELECTROAUXILIARIES; N-ACYLIMINIUM IONS; PEPTIDOMIMETICS;

AMINO ACIDS;

ACYLIMINIUM DERIVATIVE; DIPEPTIDE; PEPTIDE; PEPTIDOMIMETIC DERIVATIVE; SILANE DERIVATIVE; SILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; OXIDATION KINETICS; PEPTIDE ANALYSIS; SOLID PHASE EXTRACTION; SUBSTITUTION REACTION; SYNTHESIS;

ACYLATION; AMINO ACIDS; DIPEPTIDES; ELECTROLYSIS; IMINES; IONS; MODELS, CHEMICAL; MOLECULAR MIMICRY; ORGANOSILICON COMPOUNDS; OXIDATION-REDUCTION; PEPTIDES; SILICON;

EID: 33750283704     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064737l     Document Type: Article

References (68)

1. For recent reviews see: (a) Galeazzi, R.; Mobili, G.; Orena, M. Curr. Org. Chem. 2004, 8, 1799.
2. (b) Sagan, S.; Karoyan, P.; Lequin, O.; Chassaing, G.; Lavielle, S. Curr. Med. Chem. 2004, 11, 2799.
3. (c) Maison, W. In Highlights in Bioorganic Chemistry; Schmuck, C., Wennemers, H., Eds.; Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, Germany, 2004: pp 18-29.
4. (d) Patch, J. A.; Kirshenbaum, K.; Seurynck, S. L.; Zuckermann, R. N.; Barron, A. E. In Pseudo-Peptides in Drug Discovery; Nielsen, P. E., Ed.; Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, Germany, 2004; pp 1-31.
5. (e) Martin-Martinez, M.; Patino-Molina, R.; Garcia-Lopez, M. T.; Gozalez-Muniz, R. Mini-Rev. Med. Chem. 2004, 4, 229.
6. (f) Davies, J. S. Amino Acids, Pept., Proteins 2003, 34, 149.
7. For reviews concerning the use of lactam based peptidomimetics see: (a) Cluzeau, J.; Lubell, W. D. Biopolymers 2005, 80, 98.
8. (b) I-lalab, L.; Gosselin, F.; Lubell, W. D. Biopolymers 2000, 55, 101.
9. (c) Hanessian, S.; McNaughton-Smith, G.; Lombart. H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
10. For additional lead references see: (d) Polyak, F.; Lubell, W. D. J. Org. Chem. 1998, 63, 5937.
11. (e) Curran, T. P.; Marcaurell, L. A.; O'Sullivan, K. M. Org. Lett. 1999, 1, 1225.
12. (f) Gosselin, F.; Lubell, W. D. J. Org. Chem. 2000, 65, 2163.
13. (g) Polyak, F.; Lubell, W. D. J. Org. Chem. 2001, 66, 1171.
14. (h) Feng, Z.; Lubell, W. D. J. Org. Chem. 2001, 66, 1181.
15. For selected examples see: (a) Scott, W. L.; Alsina, J.; Kennedy, J. H.; O'Donnell, M. J. Org. Lett. 2004, 6, 1629.
16. (b) Palomo, C.; Aizpurua, J. M.; Benito, A.; Miranda, J. I.; Fratila, R. M.; Matute, C.; Domercq, M.; Gago, F.; Martin- Santamaria, S.; Linden, A. J. Am. Chem. Soc. 2003, 125, 16243.
17. (c) Colombo, L.; Di Giacomo, M.; Vinci, V.; Colombo, M.; Manzoni, L.; Scolastico, C. Tetrahedron 2003, 59, 4501.
18. (d) Dolbeare, K.; Pontoriero, G. F.; Gupta, S. K.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 2003, 46, 727.
19. (e) Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 2977.
20. (f) Aube, J. Adv. Amino Acid Mimetics Peptidomimetics 1997, 1, 193.
21. (g) Tong, Y.; Olczak, J.; Zabrocki, J.; Gershengorn, M. C.; Marshall, G. R.; Moeller K. D. Tetrahedron 2000, 56, 9791.
22. (h) Duan, S.; Moeller, K. D. Tetrahedron 2001, 57, 6407.
23. (i) Liu, B.; Brandt, J. D.; Moeller, K. D. Tetrahedron 2003, 59, 8515.
24. For examples using electrochemistry as a tool to functionalize amino acids see: (a) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113 and references therein.
25. (b) Fobian, Y. M.; d'Avignon, D. A.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1996, 6, 315.
26. (c) Fobian, Y. M.; Moeller, K. D. Methods Mol. Med. 1999, 23 (Peptidomimetic Protocols). 259.
27. (d) Tong, Y.; Fobian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. J. Org. Chem. 2000, 65, 2484.
28. (e) Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989.
29. (f) Cornille, F.; Slomczynska, U.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 909.
30. (g) Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198.
31. (h) Simpson, J. C.; Ho, C.; Shands, E. F. B.; Gershengorn, M. C.; Marshall, G. R.; Moeller, K. D. Bioorg. Med. Chem. 2002, 10, 291.
32. For a review of diversity-oriented libraries see: (a) Schreiber, S. L. Science 2000, 287, 1964.
33. In addition see: (b) Pelish, H. E.; Westwood, N. J.; Feng, Y.; Kirchhausen, T. Shair, M. D. J. Am. Chem. Soc. 2001, 123, 6740.
34. (c) Tallarico, J. A.; Depew, K. M.; Pelish, H. E.; Westwood, N. J.; Lindsley, C. W.; Shair, M. D.; Schreiber, S. L.; Foley, M. A. J. Comb. Chem. 2001, 3, 312.
35. For the use of Pd(0) catalysts on an addressable electrode microarray see: Tian, J.; Maurer, K.; Tesfu, E.; Moeller, K. D. J. Am. Chem. Soc. 2005, 127, 1392.
36. For the use of Pd(II) on an addressable electrode microarray see: (a) Tesfu, E.; Maurer, K.; Ragsdale, S. R.; Moeller, K. D. J. Am. Chem. Soc. 2004, 126, 6212.
37. (b) Tesfu, E.; Maurer, K.; Moeller, K. D. J. Am. Chem. Soc. 2006, 128, 70.
38. For the lead patent on DNA-related work involving addressable electrode microarrays see: Montgomery, D. D. PCT Int. Appl. WO 9801221, 1998, 91 pp; CODEN: PIXXD2 WO 9801221 Al 19980115.
39. For peptide-based libraries on addressable electrode microarrays see: Rossi, F. M.; Montgomery, D. D. PCT Int. Appl. WO 0053625, 2000, 52 pp; CODEN: PIXXD2 WO 0053625 A2 20000914.
40. For recent work see: Oleinikov, A. V.; Gray, M. D.; Zhao, J.; Montgomery, D. D.; Ghindilis, A. L.; Dill, K. J. Proteome Res. 2003, 2, 313.
41. (a) Yoshida J.; Isoe, S. Tetrahedron Lett. 1987, 28, 6621.
42. (b) For a review see: Yoshida, J. Top. Curr. Chem. 1994, 170, 39.
43. (c) Yoshida, J.; Wtanabe, M.; Toshioka, H.; Imagawa, M.; Suga, S. In Novel Trends in Electroorganic Synthesis; Torii, S., Ed.: Springer: Tokyo, 1998; p 99.
44. (d) Yoshida, J.; Nishiwaki, K. J. Chem. Soc., Dalton Trans. 1998, 2589.
45. For several recent applications see: (a) Kamada, T.; Oku, A. J. Chem. Soc., Perkin Trans 1 1998, 3381.
46. (b) Cao, Y.; Hidaka, A.; Tajima, T.; Fuchigami, T. J. Org. Chem. 2005, 70, 9614.
47. (c) Suga, S.; Watanabe, M.; Yoshida, J. J. Am. Chem. Soc. 2002, 124, 14824.
48. (d) Yoshida, J.; Suga, S.; Fuke, K.; Watanabe, M. Chem. Lett. 1999, 251.
49. (e) Suzuki, S.; Matsumoto, K.; Kawamura, K.; Suga, S.; Yoshida, J. Org. Lett. 2004, 6, 3755.
50. In addition to ref 4a-g see: Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106.
51. (a) For a review see: Fleming, I. In Organocopper Reagents; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, U.K., 1994; pp 257-292.
52. (b) See also: Lee, T. W.; Corey, E. J. Org. Lett. 2001, 3, 3337.
53. Sun, H. Ph.D. Thesis, Washington University, St. Louis, July 2003.
54. For a similar observation see: Martin, S. F.; Bur, S. K. Tetrahedron 1999, 55, 8905.
55. For the previous use of a phenylsulfonyl leaving group for N-acyliminium ion formation see: Brown, D. S.; Charreau, P.; Hansson, T.; Ley, S. V. Tetrahedron 1991, 47, 1311.
56. Wong, P. L.; Moeller, K. D. J. Am. Chem. Soc. 1993, 115, 11434.
57. (a) Fukuyama, T.; Jow, C. K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
58. (b) Bowman, W. R.; Coghlan, D. R. Tetrahedron 1997, 46, 15787.
59. Frey, D. A.; Wu, N.; Moeller, K. D. Tetrahedron Lett. 1996, 37, 8317. The reaction was monitored by TLC for the disappearance of substrate.
60. For the parallel synthesis of amide derivatives see: Siu, T.; Li, W.; Yudin, A. K. J. Comb. Chem. 2000, 2, 545.
61. For a review see: (a) Yudin, A. K.; Siu, T. Curr. Opin. Chem. Biol. 2001, 5, 269.
62. See also: (b) Yudin, A. K.; Siu, T.; Li, W. Patent WO 2001094666.
63. For a review see: (a) Yoshida, J.; Suga, S. Chem.-Eur. J. 2002, 8, 2650. For recent examples see reference IIe and references therein.
64. (a) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841.
65. (b) Kim, H.-J.; Yoon, U.-C.; Jung, Y.-S.; Park, N. S.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 860.
66. Wang, L.; Seiders, J. R., II.; Floreancig, P. E. J. Am. Chem. Soc. 2004, 126, 12596.
67. Yoshida, J.-i.; Watanabe, M.; Toshioka, H.; Imagawa, M.; Suga, S. J. Electroanal. Chem. 2001, 507 (1-2), 55-65.
68. For the literature synthesis of 56 please see: Ankianiec, B. C.; Young, G. B. Polyhedron 1995, 14, 249.