Solid-phase and solution-phase syntheses of oligomeric guanidines bearing peptide side chains

Journal of Organic Chemistry

Volumn 70, Issue 22, 2005, Pages 8801-8810

  Zhang, Zhongsheng ^a   Fan, Erkang ^a  

^a UNIVERSITY OF WASHINGTON SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CARBOXYLIC ACIDS; MONOMERS; SOLID SOLUTIONS; SYNTHESIS (CHEMICAL);

CARBODIIMIDE INTERMEDIATE; OLIGOMER ELONGATION; OLIGOMERIC GUANIDINES; PEPTIDE SIDE CHAINS;

OLIGOMERS;

ALKYL GROUP; AMIDE; AROMATIC COMPOUND; CARBOXYLIC ACID; GLUTAMIC ACID DERIVATIVE; GUANIDINE DERIVATIVE; HYDROXYL GROUP; MONOMER; OLIGOMER; PEPTIDE; PROLINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; STRUCTURE ANALYSIS; SYNTHESIS;

CHROMATOGRAPHY, LIQUID; CYCLIZATION; GUANIDINES; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PEPTIDES; PHASE TRANSITION; SOLUTIONS;

EID: 27444438904     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051226t     Document Type: Article

References (45)

1. Geysen, H. M.; Meloen, R. H.; Barteling, S. J. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 3998-4002.
2. Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. Nature 1991, 354, 82-84.
3. Houghten, R. A.; Pinilla, C.; Blondelle, S. E.; Appel, J. R.; Dooley, C. T.; Cuervo, J. H. Nature 1991, 354, 84-86.
4. Soth, M. J.; Nowick, J. S. Curr. Opin. Chem. Biol. 1997, 1, 120-129.
5. Schneider, S. E.; Anslyn, E. V. In Advances in Supramolecular Chemistry; Gokel, G. W., Ed.; 1999; Vol. 5, pp 55-120.
6. Kirshenbaum, K.; Zuckermann, R. N.; Dill, K. A. Curr. Opin. Struct. Biol. 1999, 9, 530-535.
7. Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219-3232.
8. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4011.
9. Oh, K.; Jeong, K. S.; Moore, J. S. Nature 2001, 414, 889-893.
10. Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913-941.
11. Zuckermann, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646-10647.
12. Kruijtzer, J. A. W.; Lefeber, D. J.; Liskamp, R. M. J. Tetrahedron Lett. 1997, 38, 5335-5338.
13. Cho, C. Y.; Moran, E. J.; Cherry, S. R.; Stephans, J. C.; Fodor, S. P. A.; Adams, C. L.; Sundaram, A.; Jacobs, J. W.; Schultz, P. G. Science 1993, 261, 1303-1305.
14. Burgess, K.; Linthicum, D. S.; Shin, H. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 907-909.
15. Kim, J. M.; Bi, Y. Z.; Paikoff, S. J.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5305-5308.
16. Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556-1564.
17. Boeijen, A.; van Ameijde, J.; Liskamp, R. M. J. J. Org. Chem. 2001, 66, 8454-8462.
18. Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 2539-2544.
19. Cheguillaume, A.; Salaun, A.; Sinbandhit, S.; Potel, M.; Gall, P.; Baudy-Floc'h, M.; Le Grel, P. J. Org. Chem. 2001, 66, 4923-4929.
20. Seidler, J.; McGovern, S. L.; Doman, T. N.; Shoichet, B. K. J. Med. Chem. 2003, 46, 4477-4486.
21. Jenks, W. P.; Regenstein, J. In Handbook of Biochemistry. Selected Data for Molecular Biology; Sober, H. A., Ed.; CRC Press: Cleveland, 1985.
22. Barawkar, D. A.; Bruice, T. C. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 11047-11052.
23. Dempcy, R. O.; Luo, J.; Bruice, T. C. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 4326-4330.
24. Linkletter, B. A.; Bruice, T. C. Bioorg. Med. Chem. Lett. 1998, 8, 1285-1290.
25. Linkletter, B. A.; Szabo, I. E.; Bruice, T. C. J. Am. Chem. Soc. 1999, 121, 3888-3896.
26. Linkletter, B. A.; Bruice, T. C. Bioorg. Med. Chem. 2000, 8, 1893-1901.
27. Tanatani, A.; Kagechika, H.; Azumaya, I.; Fukutomi, R.; Ito, Y.; Yamaguchi, K.; Shudo, K. Tetrahedron Lett. 1997, 38, 4425-4428.
28. Schneider, S. E.; Bishop, P. A.; Salazar, M. A.; Bishop, O. A.; Anslyn, E. V. Tetrahedron 1998, 54, 15063-15086.
29. Tanatani, A.; Yamaguchi, K.; Azumaya, I.; Fukutomi, R.; Shudo, K.; Kagechika, H. J. Am. Chem. Soc. 1998, 120, 6433-6442.
30. Zhang, Z.; Carter, T.; Fan, E. Tetrahedron Lett. 2003, 44, 3063-3066.
31. Rodriguez, M.; Llinares, M.; Doulut, S.; Heitz, A.; Martinez, J. Tetrahedron Lett. 1991, 32, 923-926.
32. Zhang, Z.; Pickens, J. C.; Hol, W. G. J.; Fan, E. Org. Lett. 2004, 6, 1377-1380.
33. Chang, C.-D.; Waki, M.; Ahmad, M.; Meienhofer, J.; Lundell, E. O.; Huag, J. D. Int. J. Pept. Protein Res. 1980, 15, 59.
34. SheppeckII, J. E.; Kar, H.; Hong, H. Tetrahedron Lett. 2000, 41, 5329-5333.
35. Kim, J.-M.; Bi, Y.; Paikoff, S. J.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5305-5308.
36. Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427-1430.
37. Bartra, M.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron 1990, 46, 587-594.
38. Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. J. Org. Chem. 2000, 65, 1566-1568.
39. Evindar, G.; Batey, R. A. Org. Lett. 2003, 5, 1201-1204.
40. Bloomberg, G. B.; Askin, D.; Gargaro, A. R.; Tanner, M. J. A. Tetrahedron Lett. 1993, 34, 4709-4712.
41. Augustyns, K.; Kraas, W.; Jung, G. J. Pept. Res. 1998, 51, 127-133.
42. Chhabra, S. R.; Hothi, B.; Evans, D. J.; White, P. D.; Bycroft, B. W.; Chan, W. C. Tetrahedron Lett. 1998, 39, 1603-1606.
43. Alper, P. B.; Hung, S.-C.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 6029-6032.
44. Lundquist, J. T.; Pelletier, J. C. Org. Lett. 2001, 3, 781-783.
45. Rijkers, D. T. S.; van Vugt, H. H. R.; Jacobs, H. J. F.; Liskamp, R. M. J. Tetrahedron Lett. 2002, 43, 3657-3660.