Biological tuning of synthetic tactics in solid-phase synthesis: Application to Aβ(1-42)

Journal of Organic Chemistry

Volumn 69, Issue 22, 2004, Pages 7776-7778

  Kim, Young Soo ^a   Moss, Jason A ^a   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; ORGANIC POLYMERS; REDUCTION; RESINS; SOLUTIONS; SULFUR COMPOUNDS;

ON-RESIN REDUCTION; PEPTIDES; SOLID-PHASE SYNTHESIS; SULFOXIDES;

SYNTHESIS (CHEMICAL);

AMYLOID BETA PROTEIN[1-42]; METHIONINE SULFOXIDE; PEPTIDE DERIVATIVE; RESIN; SULFOXIDE;

ALZHEIMER DISEASE; AMINO ACID SEQUENCE; ARTICLE; CATALYSIS; CONFORMATIONAL TRANSITION; OLIGOMERIZATION; OXIDATION REDUCTION REACTION; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PROTEIN AGGREGATION; PROTEIN ASSEMBLY; PROTEIN DEGRADATION; PROTEIN FUNCTION; PROTEIN MODIFICATION; PROTEIN PURIFICATION; PROTEIN STRUCTURE; REDUCTION; REPRODUCIBILITY; SOLID; STRUCTURE ACTIVITY RELATION; TECHNIQUE;

AMYLOID BETA-PROTEIN; CHEMISTRY, ORGANIC; METHIONINE; OXIDATION-REDUCTION; PEPTIDE FRAGMENTS; SULFOXIDES;

EID: 6344219786     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048922y     Document Type: Article

References (38)

1. Walsh, D. M.; Klyubin, L.; Fadeeva, J. V.; Rowan, M. J.; Selkoe, D. J. Biochem. Soc. T 2002, 30, 552-557.
2. Jablonowska, A.; Dadlez, M. Polimery 2003, 48, 35-43.
3. Kayed, R.; Head, E.; Thompson, J. L.; McIntire, T. M.; Milton, S. C.; Cotman, C. W.; Glabe, C. G. Science 2003, 300, 486-489.
4. Dahlgren, K. N.; Manelli, A. M.; Stine, W. B.; Baker, L. K.; Krafft, G. A.; LaDu, M. J. J. Biol. Chem. 2002, 277, 32046-32053.
5. Roher, A. E.; Chaney, M. O.; Kuo, Y. M.; Webster, S. D.; Stine, W. B.; Haverkamp, L. J.; Woods, A. S.; Cotter, R. J.; Tuohy, J. M.; Krafft, G. A.; Bonnell, B. S.; Emmerling, M. R. J. Biol. Chem. 1996, 271, 20631-20635.
6. Kuo, Y. M.; Emmerling, M. R.; VigoPelfrey, C.; Kasunic, T. C.; Kirkpatrick, J. B.; Murdoch, G. H.; Ball, M. J.; Roher, A. E. J. Biol. Chem. 1996, 271, 4077-4081.
7. Shoji, M.; Kawarabayashi, T.; Sato, M.; Sasaki, A.; Saido, T. C.; Matsubara, E.; Tomidokoro, Y.; Kanai, M.; Shizuka, M.; Ishiguro, K.; Ikeda, M.; Harigaya, Y.; Okamoto, K.; Hirai, S. J. Pathol. 2000, 191, 93-101.
8. Janciauskiene, S.; Wright, H. T.; Lindgren, S. Neuropeptides 1999, 33, 510-516.
9. Fukuda, H.; Shimizu, T.; Nakajima, M.; Mori, H.; Shirasawa, T. Bioorg. Med. Chem. Lett. 1999, 9, 953-956.
10. Wisniewski, H. M.; Sadowski, M.; Jakubowska-Sadowska, K.; Tarnawski, M.; Wegiel, J. J. Neuropathol. Exp. Neurol. 1998, 57, 674-683.
11. Blanchard, B. J.; Konopka, G.; Russell, M.; Ingram, V. M. Brain Res. 1997, 776, 40-50.
12. Varadarajan, S.; Yatin, S.; Butterfield, D. A. Alzheimers Rep. 2000, 3, 71-76.
13. Schoneich, C.; Pogocki, D.; Hug, G. L.; Bobrowski, K. J. Am. Chem. Soc. 2003, 125, 13700-13713.
14. Dong, J.; Atwood, C. S.; Anderson, V. E.; Siedlak, S. L.; Smith, M. A.; Perry, G.; Carey, P. R. Biochemistry 2003, 42, 2768-2773.
15. Butterfield, D. A.; Kanski, J. Peptides 2002, 23, 1299-1309.
16. Curtain, C. C.; Ali, F.; Volitakis, I.; Cherny, R. A.; Norton, R. S.; Beyreuther, K.; Barrow, C. J.; Masters, C. L.; Bush, A. I.; Barnham, K. J. J. Biol. Chem. 2001, 276, 20466-20473.
17. Liu, S. T.; Hewlett, G.; Barrow, C. J. Biochemistry 1999, 38, 9373-9378.
18. Balakrishnan, R.; Parthasarathy, R.; Sulkowski, E. J. Peptide Res. 1998, 51, 91-95.
19. Williams, A. D.; Portelius, E.; Kheterpal, I.; Guo, J. T.; Cook, K. D.; Xu, Y.; Wetzel, R. J. Mol. Biol. 2004, 335, 833-842.
20. Varadarajan, S.; Yatin, S.; Kanski, J.; Jahanshahi, F.; Butterfield, D. A. Brain Res. Bull. 1990, 50, 133-141.
21. Leissring, M. A.; Lu, A.; Condron, M. M.; Teplow, D. B.; Stein, R. L.; Farris, W.; Selkoe, D. J. J. Biol. Chem. 2003, 278, 37314-37320.
22. Egnaczyk, G. F.; Greis, K. D.; Stimson, E. R.; Maggio, J. E. Biochemistry 2001, 40, 11706-11714.
23. Hou, L. M.; Rang, I.; Marchant, R. E.; Zagorski, M. G. J. Biol. Chem. 2002, 277, 40173-40176.
24. Palmblad, M.; Westlind-Danielsson, A.; Bergquist, J. J. Biol. Chem. 2002, 277, 19506-19510.
25. Watson, A. A.; Fairlie, D. P.; Craik, D. J. Biochemistry 1998, 37, 12700-12706.
26. Hou, L. M.; Shao, H. Y.; Zhang, Y. B.; Li, H.; Menon, N. K.; Neuhaus, E. B.; Brewer, J. M.; Byeon, I. J. L.; Ray, D. G.; Vitek, M. P.; Iwashita, T.; Makula, R. A.; Przybyla, A. B.; Zagorski, M. G. J. Am. Chem. Soc. 2004, 126, 1992-2005.
27. Kent, S. B. H. In Peptides: Structure and Function. Proceedings of the Ninth American Peptide Symposium; Deber, C. M., Hruby, V. J., Kopple, K. D., Eds.; Pierce Chemical Co.: Rockford, IL, 1985; pp 407-414.
28. Hyde, C.; Johnson, T.; Sheppard, R. C. J. Chem. Soc., Chem. Commun. 1992, 1573-1575.
29. Miranda, L. P.; Alewood, P. F. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 1181-1186.
30. Pugh, K. C.; York, E. J.; Stewart, J. M. Int. J. Peptide Protein Res. 1992, 40, 208-213.
31. Hendrix, J. C.; Jarrett, J. T.; Anisfeld, S. T.; Lansbury, P. T. J. Org. Chem. 1992, 57, 3414-3420.
32. Fields, G. B.; Fields, C. G. J. Am. Chem. Soc. 1991, 113, 4202-4207.
33. Tam, J. P. Int. J. Peptide Protein Res. 1987, 29, 421-431.
34. Heath, W. F.; Tam, J. P.; Merrifield, R. B. Int. J. Peptide Protein Res. 1986, 28, 498-507.
35. Schnolzer, M.; Alewood, P.; Jones, A.; Alewood, D.; Kent, S. B. H. Int. J. Peptide Protein Res. 1992, 40, 180-193.
36. Tam, J. P.; Heath, W. F.; Merrifield, R. B. J. Am. Chem. Soc. 1983, 105, 6442-6455.
37. Patek, M.; Lebl, M. Tetrahedron Lett. 1991, 32, 3891-3894.
38. Kiso, Y.; Fukui, T.; Tanaka, S.; Kimura, T.; Akaji, K. Tetrahedron Lett. 1994, 35, 3571-3574.