Versatile synthesis of stable, functional polypeptides via reaction with epoxides

Biomacromolecules

Volumn 16, Issue 6, 2015, Pages 1802-1806

  Gharakhanian, Eric G ^a   Deming, Timothy J ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Engineering IV   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; AMINO ACIDS;

CHEMOSELECTIVE; DEALKYLATION; FUNCTIONALIZATIONS; METHIONINE RESIDUES; STERICALLY DEMANDING;

FUNCTIONAL GROUPS;

EPOXIDE; METHIONINE; SULFONIUM DERIVATIVE; PEPTIDE;

ALKYLATION; ARTICLE; DEALKYLATION; GLYCOSYLATION; METHODOLOGY; PRIORITY JOURNAL; PROTEIN FUNCTION; PROTEIN STABILITY; PROTEIN SYNTHESIS; REACTION ANALYSIS; CHEMISTRY; SYNTHESIS;

ALKYLATION; EPOXY COMPOUNDS; METHIONINE; PEPTIDES;

EID: 84930959826     PISSN: 15257797     EISSN: 15264602     Source Type: Journal    
DOI: 10.1021/acs.biomac.5b00372     Document Type: Article

References (30)

1. Gauthier, M. A.; Gibson, M. I.; Klok, H.-A. Angew. Chem., Int. Ed. 2009, 48, 48-58
2. Slavin, S.; Burns, J.; Haddleton, D. M.; Becer, C. R. Eur. Polym. J. 2011, 47, 435-446
3. Barner-Kowollik, C.; Du Prez, F. E.; Espeel, P.; Hawker, C. J.; Junkers, T.; Schlaad, H.; Van Camp, W. Angew. Chem., Int. Ed. 2011, 50, 60-62
4. Deming, T. J. WIREs Nanomed. Nanobiotechnol. 2014, 6, 283-297
5. Engler, A. C.; Lee, H.-I.; Hammond, P. T. Angew. Chem., Int. Ed. 2009, 48, 9334-9338
6. Cheng, Y.; He, C.; Xiao, C.; Ding, J.; Zhuang, X.; Chen, X. Polym. Chem. 2011, 2, 2627-2634
7. Huang, Y.; Zeng, Y.; Yang, J.; Zeng, Z.; Zhu, F.; Chen, X. Chem. Commun. 2011, 47, 7509-7511
8. Huang, J.; Habraken, G.; Audouin, F.; Heise, A. Macromolecules 2010, 43, 6050-6057
9. Sun, J.; Schlaad, H. Macromolecules 2010, 43, 4445-4448
10. Lu, H.; Bai, Y.; Wang, J.; Gabrielson, N. P.; Wang, F.; Lin, Y.; Cheng, J. Macromolecules 2011, 44, 6237-6240
11. Tang, H.; Zhang, D. Polym. Chem. 2011, 2, 1542-1551
12. Tang, H.; Zhang, D. Biomacromolecules 2010, 11, 1585-1592
13. Habraken, G. J. M.; Koning, C. E.; Heuts, J. P. A.; Heise, A. Chem. Commun. 2009, 45, 3612-3614
14. Rhodes, A. J.; Deming, T. J. ACS Macro Lett. 2013, 2, 351-354
15. Kramer, J. R.; Deming, T. J. Biomacromolecules 2012, 13, 1719-1723
16. Kramer, J. R.; Deming, T. J. Chem. Commun. 2013, 49, 5144-5146
17. Fraenkel-Conrad, H. J. Biol. Chem. 1944, 154, 227-238
18. Starbuck, W. C.; Busch, H. Biochim. Biophys. Acta 1963, 78, 594-605
19. Windmueller, H. G.; Ackerman, C. J.; Engel, R. W. J. Biol. Chem. 1959, 234, 895-899
20. Zilkha, A.; Rappoport, S. J. Org. Chem. 1963, 28, 1105-1107
21. Sheng, L.-S.; Horning, E. C.; Horning, M. C. Drug Metab. Dispos. 1984, 12, 297-303
22. Alferiev, I. S.; Hinson, J. T.; Ogle, M.; Breuer, E.; Levy, R. J. Biomaterials 2001, 22, 2501-2506
23. Kramer, J. R.; Deming, T. J. Polym. Chem. 2014, 5, 671-682
24. Liu, Y.; Chen, P.; Li, Z. Macromol. Rapid Commun. 2012, 33, 287-295
25. Bleek, K.; Taubert, A. Acta Biomater. 2013, 9, 6283-6321
26. Lowe, A. B.; McCormick, C. L. Chem. Rev. 2002, 102, 4177-4189
27. Jones, J. B.; Hysert, D. W. Can. J. Chem. 1971, 49, 3012-3019
28. Chalker, J. M.; Bernardes, G. J. L.; Lin, Y. A.; Davis, B. G. Chem.-Asian J. 2009, 4, 630-640
29. Reid, G. E.; Roberts, K. D.; Simpson, R. J.; O'Hair, R. A. J. J. Am. Soc. Mass Spectrom. 2005, 16, 1131-1150
30. Roberts, K. D.; Reid, G. E. J. Mass Spectrom. 2007, 42, 187-198