Benzotriazole-assisted solid-phase assembly of Leu-Enkephalin, amyloid β segment 34-42, and other "difficult" peptide sequences

Journal of Organic Chemistry

Volumn 74, Issue 5, 2009, Pages 2028-2032

  Katritzky, Alan R ^a   Haase, Danniebelle N ^a   Johnsons, Jodie V ^b   Chung, Alfred ^a  

^a UNIVERSITY OF FLORIDA   (United States)

^b NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOACYL; BENZOTRIAZOLE; BENZOTRIAZOLES; MICROWAVE-ASSISTED; PEPTIDE SEQUENCES; SOLID-PHASE; SOLID-PHASE SYNTHESIS;

GLYCOPROTEINS; PEPTIDES;

AMINES;

AMYLOID BETA PEPTIDE[34-42]; AMYLOID BETA PROTEIN; BENZOTRIAZOLE DERIVATIVE; LEUCINE ENKEPHALIN; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; AMINOACYLATION; ARTICLE; DEPROTECTION REACTION; MICROWAVE THERAPY; PEPTIDE SYNTHESIS; RACEMIZATION; SOLID; SOLID PHASE SYNTHESIS;

AMYLOID BETA-PROTEIN; ENKEPHALIN, LEUCINE; MICROWAVES; MOLECULAR STRUCTURE; OLIGOPEPTIDES; PEPTIDE FRAGMENTS; TRIAZOLES;

EID: 64249159629     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8026214     Document Type: Article

References (38)

1. (a) Quibell, M.; Johnson, T. In Difficult Peptides: Fmoc Solid Phase Peptide Synthesis; A Practical Approach; Chan, W. C., White, P. D., Eds.; Oxford University Press: New York, 2000; pp 115-117.
2. (b) Lloyd-Williams, P.; Albericio, F.; Giralt, E. Introduction: Chemical Approaches to the Synthesis of Peptides and Proteins; CRC Press: Boca Raton, FL, 1997; pp 1-17.
3. (c) Cameron, L. R.; Holder, J. L.; Meldal, M.; Sheppard, R. C. J. Chem. Soc., Perkin Trans. 1 1988, 14, 2895-2901.
4. (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154.
5. (b) Merrifield, B. Science 1986, 232, 341-347.
6. (a) Kent, S. B. H. Annu. Rev. Biochem. 1988, 57, 957-989.
7. (b) De L. Milton, R. C.; Milton, S. C. F.; Adams, P. A. J. Am. Chem. Soc. 1990, 112, 6039-6046.
8. (c) Hyde, C.; Johnson, T.; Owen, D.; Quibell, M.; Sheppard, R. C. Int. J. Peptide Protein Res. 1994, 43, 431-440.
9. (d) Tam, J. P.; Lu, Y. A. J. Am. Chem. Soc. 1995, 117, 12058-12063.
10. (a) Chan, W. C.; White, P. D. In Basic Principles: Fmoc Solid Phase Peptide Synthesis; A Practical Approach; Chan, W. C., White, P. D., Eds.; Oxford University Press: New York, 2000; pp 32-36.
11. (b) Mergler, M.; Dick, F.; Sax, B.; Stähelin, C.; Vorherr, T. J. Peptide Sci. 2003, 9, 518-526.
12. (c) Palasek, S. A.; Cox, Z. J.; Collins, J. M. J. Peptide Sci. 2007, 13, 143-148.
13. (a) Sohma, Y.; Sasaki, M.; Hayashi, Y.; Kimura, T.; Kiso, Y. Chem. Commun. 2004, 1, 124-125.
14. (b) Sohma, Y.; Taniguchi, A.; Skwarczynski, M.; Yoshiya, T.; Fukao, F.; Kimura, T.; Hayashi, Y.; Kiso, Y. Tetrahedron Lett. 2006, 47, 3013-3017.
15. Katritzky, A. R.; Khashab, N. M.; Yoshioka, M.; Haase, D. N.; Wilson, K. R.; Johnson, J. V.; Chung, A.; Haskell-Luevano, C. Chem. Biol. Drug Des. 2007, 70, 465-468.
16. (a) Packman, L. C. Tetrahedron Lett. 1995, 36, 7523-7526.
17. (b) Quibell, M.; Packman, L. C.; Johnson, T. J. Am. Chem. Soc. 1995, 117, 11656-11668.
18. (c) Miranda, L. P.; Meutermans, W. D. F.; Smythe, M. L.; Alewood, P. F. J. Org. Chem. 2000, 65, 5460-5468.
19. (d) Katritzky, A. R.; Singh, A.; Haase, D. N.; Yoshioka, M. Arkivoc 2009, 47-56.
20. (e) Technical Bulletin, Applied. Biosystems.
21. (a) Crich, D.; Banerjee, A. J. Org. Chem. 2006, 71, 7106-7109.
22. (b) Cremonesi, G.; Dalla, Croce, P.; Fontana, F.; Forni, A.; La Rosa, C. Tetrahedron: Asymmetry 2007, 18, 1667-1675.
23. (c) Davis, F. A.; Srirajan, V.; Fanelli, D. L.; Portonovo, P. J. Org. Chem. 2000, 65, 7663-7666.
24. (d) Kimura, T.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742.
25. Di Fenza, A.; Tancredi, M.; Galoppini, C.; Rovero, P. Tetrahedron Lett. 1998, 39, 8529-8532.
26. (a) Bedford, J.; Hyde, C.; Johnson, T.; Jun, W.; Owen, D.; Quibell, M.; Sheppard, R. C. Int. J. Pept. Prot. Res. 1992, 40, 300-307.
27. (b) Kates, S. A.; Sole, N. A.; Beyermann, M.; Barany, G.; Albericio, F. Peptide Res. 1996, 9, 106.
28. (a) Pátek, M. Branched-Chain Amino Acids. In Amino Acid Biosynthesis-Pathways, Regulation and Metabolic Engineering; Wendisch, V. F., Ed.; Microbiology Monographs; Springer-Verlag: Berlin, Heidelberg, New York, 2007; Vol. 5, pp 129-162.
29. (b) Cornish, V. W.; Kaplan, M. I.; Veenstra, D. L.; Kollman, P. A.; Schultz, P. G. Biochemistry 1994, 33, 12022-12031.
30. Ajikumar, P. K.; Devaky, K. S. J. Pept. Sci. 2001, 7, 641-649.
31. Skropeta, D.; Jolliffe, K. A.; Turner, P. J. Org. Chem. 2004, 69, 8804-8809.
32. Wade, J. D.; Mathieu, M. N.; Macris, M.; Tregear, G. W. Lett. Pept. Sci. 2000, 7, 107-112.
33. Zahariev, S.; Guarnaccia, C.; Pongor, C. I.; Quaroni, L.; Čemažar, M.; Pongor, S. Tetrahedron Lett. 2006, 47, 4121-4124.
34. Albericio, F.; Nicola's, E.; Josa, J.; Grandas, A.; Pedroso, E.; Giralt, E.; Granier, C.; van Rietschoten, J. Tetrahedron 1987, 43, 5961-5971.
35. Thieriet, N.; Guibé, F.; Albericio, F. Org. Lett. 2000, 2, 1815-1817.
36. Tickler, A. K.; Clippingdale, A. B.; Wade, J. D. Protein Peptide Lett. 2004, 11, 377-384.
37. Halverson, K.; Fraser, P. E.; Kirschner, D. A.; Lansbury, P. T. Biochemistry 1990, 29, 2639-2644.
38. Wehrstedt, K. D.; Wandrey, P. A.; Heitkamp, D. J. Hazard. Mater. 2005, A126, 1-7.