Protease catalyzed in situ C-Terminal modification of oligoglutamate

Macromolecules

Volumn 43, Issue 12, 2010, Pages 5245-5255

  Viswanathan, Kodandaraman ^a   Li, Geng ^a   Gross, Richard A ^a  

^a POLYTECHNIC UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYL ACCEPTOR; AMINE GROUPS; AROMATIC RINGS; BENZYLAMINES; BROMELAIN; CARBOXYL GROUPS; END-GROUPS; FEED RATIOS; FUNCTIONALIZED; IN-SITU; L-HISTIDINE; L-PHENYLALANINE; MALDI-TOF; METHYL AMINE; MOLECULAR IONS; MONOFUNCTIONAL; OLIGOPEPTIDES; ONE POT; PEPTIDE SYNTHESIS; TERMINAL GROUPS; TERMINAL MODIFICATIONS;

AMINO ACIDS; NUCLEOPHILES; OLIGOMERIZATION; PEPTIDES; PHOSPHATASES; THIOPHENE;

ORGANIC COMPOUNDS;

EID: 77953681550     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma100562j     Document Type: Article

References (42)

1. Smeenk, J. M.; Ayers, L.; Stunnenberg, H. G.; van Hest, J. C. M. Macromol. Symp. 2005, 225, 1-8
2. Ayres, L.; Adams, P. H. H. M.; Löwik, D. W. P. M.; van Hest, J. C. M. Biomacromolecules 2005, 6, 825-831
3. Smeenk, J. M.; Otten, M. B. J.; Thies, J.; Tirrell, D. A.; Stunnenberg, H. G.; van Hest, J. C. M. Angew. Chem., Int. Ed. 2005, 44, 1968-1971
4. OBrien-Simpson, N. M.; Ede, N. J.; Brown, L. E.; Swan, J.; Jackson, D. C. J. Am. Chem. Soc. 1997, 119, 1183-1188
5. Herrmann, A.; Mihov, G.; Vandermeulen, G. W. M.; Klok, H.-A.; Müllen, K. Tetrahedron 2003, 59, 3925-3935
6. Orwig, K. S.; Dix, T. A. Tetrahedron Lett. 2005, 46, 7007-7009
7. Yeo, W.-S.; Yousaf, M. N.; Mrksich, M. J. Am. Chem. Soc. 2003, 125, 14994-14995
8. Biagini, L. C. G.; Parry, A. L. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 3178-3190
9. Bielawski, C. W.; Grubbs, R. H. Prog. Polym. Sci. 2007, 32, 1-29
10. Houseman, B. T.; Huh, J. H.; Kron, S. J.; Mrksich, M. Nat. Biotechnol. 2002, 20, 270-274
11. Sadler, K.; Zeng, W.; Jackson, D. C. J. Pept. Res. 2002, 60, 150-158
12. Maskarinec, S. A.; Tirrell, D. A. Curr. Opin. Biotechnol. 2005, 16, 422-426
13. Yoshikawa, E.; Fournier, M. J.; Mason, T. L.; Tirrell, D. A. Macromolecules 2002, 27, 5471-5475
14. Kothakota, S.; Mason, T. L.; Tirrell, D. A.; Fournier, M. J. J. Am. Chem. Soc. 2002, 117, 536-537
15. van Hest, J. C. M.; Kiick, K. L.; Tirrell, D. A. J. Am. Chem. Soc. 2000, 122, 1282-1288
16. Enzymes in Synthetic Organic Chemistry, 1st ed.; Whitesides, W. A., Ed.; Academic Press: New York, 1994; Vol. 12.
17. Keiichi Aso, T. U.; Shiokawa, Y. Agric. Biol. Chem. 1988, 52, 2443-2449
18. Uemura, T. F. M.; Lee, H.-H.; Ikeda, S.; Aso, K. Agric. Biol. Chem. 1990, 54, 2277-2281
19. Uyama, H.; Fukuoka, T.; Komatsu, I.; Watanabe, T.; Kobayashi, S. Biomacromolecules 2002, 3, 318-323
20. Matsumura, S.; Tsushima, Y.; Otozawa, N.; Murakami, S.; Toshima, K.; Swift, G. Macromol. Rapid Commun. 1999, 20, 7-11
21. Soeda, Y.; Toshima, K.; Matsumura, S. Biomacromolecules 2003, 4, 196-203
22. Li, G.; Vaidya, A.; Viswanathan, K.; Cui, J.; Xie, W.; Gao, W.; Gross, R. A. Macromolecules 2006, 39, 7915-7921
23. Li, G.; Raman, V. K.; Xie, W.; Gross, R. A. Macromolecules 2008, 41, 7003-7012
24. Heck, T.; Kohler, H.-P. E.; Limbach, M.; Flögel, O.; Seebach, D.; Geueke, B. Chem. Biodiversity 2007, 4, 2016-2030
25. Fernandez, M. M.; Margot, A. O.; Falender, C. A.; Blanch, H. W.; Clark, D. S. Enzyme Microb. Technol. 1995, 17, 964-971
26. Lang, A.; Hatscher, C.; Wiegert, C.; Kuhl, P. Amino Acids 2009, 36, 333-340
27. Schuster, M.; Aaviksaar, A.; Jakubke, H. D. Tetrahedron 1990, 46, 8093-8102
28. Ito, T.; Sugita, Y.; Takao, K.; Ikeguchi, Y.; Shirahata, A. Biol. Pharm. Bull. 2007, 30, 1838-1843
29. Günther, R.; Bordusa, F. Chem. - Eur. J. 2000, 6, 463-467
30. Widmer, F.; Breddam, K.; Johansen, J. T. Carlsberg Res. Commun. 1981, 46, 97-106
31. Bordusa, F. Braz. J. Med. Biol. Res. 2000, 33, 469-485
32. Bordusa, F. Chem. Rev. 2002, 102, 4817-4868
33. Jakubke, H.-D.; Kuhl, P.; Könnecke, A. Angew. Chem., Int. Ed. Engl. 1985, 24, 85-93
34. Smith, P. K.; Krohn, R. I.; Hermanson, G. T.; Mallia, A. K.; Gartner, F. H.; Provenzano, M. D.; Fujimoto, E. K.; Goeke, N. M.; Olson, B. J.; Klenk, D. C. Anal. Biochem. 1985, 150, 76-85
35. Wiechelman, K. J.; Braun, R. D.; Fitzpatrick, J. D. Anal. Biochem. 1988, 175, 231-237
36. Richardson, T.; Finley, J. W., Eds. Chemical Changes in Food During Processing; Springer: New York, 1986.
37. Yamashita, M.; Arai, S.; Kokubo, S.; Aso, K.; Fujimaki, M. J. Agric. Food. Chem. 2002, 23, 27-30
38. Schuster, M.; Munoz, B.; Yuan, W.; Wong, C. H. Tetrahedron Lett. 1993, 34, 1247-1250
39. Eichhorn, U.; Bommarius, A. S.; Drauz, K.; Jakubke, H.-D. J. Pept. Sci. 1997, 3, 245-251
40. Zimmerman, M. P.; Smith, R. E.; Becker, M. U.S. Patent 5,714,484, 1998.
41. Serge, L.; Christopher, B.; Jean-Francois, T. Cathepsin cysteine-protease inhibitiors. WO Patent 2007.
42. Wilder, P.; Knight, D. B. J. Org. Chem. 1965, 30, 3078-3081