Optimization and expansion of a site-selective N-methylpyridinium-4-carboxaldehyde-mediated transamination for bacterially expressed proteins

Journal of the American Chemical Society

Volumn 137, Issue 3, 2015, Pages 1123-1129

  Palla, Kanwal S ^a   Witus, Leah S ^a   Mackenzie, Katherine J ^a   Netirojjanakul, Chawita ^a   Francis, Matthew B ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHEMICAL REACTIONS; ESCHERICHIA COLI; EXCITONS; FUNCTIONAL GROUPS; KETONES;

CHEMICAL ATTACHMENT; CHEMICAL EQUATIONS; PROTEIN MODIFICATIONS; PROTEIN-BASED MATERIALS; PROTEOLYTIC CLEAVAGE; PYROCOCCUS HORIKOSHII; SITE DIRECTED MUTAGENESIS; SPECIFIC FUNCTIONAL GROUPS;

PROTEINS;

ALDEHYDE; BACTERIAL PROTEIN; BLOOD CLOTTING FACTOR 10A; FUNCTIONAL GROUP; GLUCAN SYNTHASE; GLUTAMIC ACID; KETONE; METHIONINE; N METHYLPYRIDINIUM 4 CARBOXALDEHYDE BENZENESULFONATE; PEPTIDES AND PROTEINS; PYRIDINIUM DERIVATIVE; REAGENT; UNCLASSIFIED DRUG; 1-METHYLPYRIDINIUM; CELLULASE; RECOMBINANT PROTEIN;

AMINO TERMINAL SEQUENCE; ARTICLE; ASSAY; ESCHERICHIA COLI; MUTANT; NONHUMAN; PROTEIN DEGRADATION; PROTEIN EXPRESSION; PROTEIN FUNCTION; PYROCOCCUS HORIKOSHII; START CODON; TERMINAL SEQUENCE; THERMOPHILIC BACTERIUM; TRANSAMINATION; WASTE; AMINATION; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; GENETICS; METABOLISM; SITE DIRECTED MUTAGENESIS;

ALDEHYDES; AMINATION; CELLULASE; ESCHERICHIA COLI; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MUTAGENESIS, SITE-DIRECTED; PYRIDINIUM COMPOUNDS; PYROCOCCUS HORIKOSHII; RECOMBINANT PROTEINS;

EID: 84921841110     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja509955n     Document Type: Article

References (34)

1. Day, J. J.; Marquez, B. V.; Beck, H. E.; Aweda, T. A.; Gawande, P. D.; Meares, C. F. Curr. Opin. Chem. Biol. 2010, 14, 803-809.
2. Miller, R. A.; Presley, A. D.; Francis, M. B. J. Am. Chem. Soc. 2007, 129, 3104-3109.
3. Alley, S. C.; Okeley, N. M.; Senter, P. D. Curr. Opin. Chem. Biol. 2010, 14, 529-537.
4. Esser-Kahn, A. P.; Iavarone, A. T.; Francis, M. B. J. Am. Chem. Soc. 2008, 130, 15820-15822.
5. Vasita, R.; Shanmugam, K.; Katti, D. S. Curr. Top. Med. Chem. 2008, 8, 341-353.
6. Basle, E.; Joubert, N.; Pucheault, M. Chem. Biol. 2010, 17, 213-227.
7. Smith, M. E. B.; Schumacher, F. F.; Ryan, C. P.; Tedaldi, L. M.; Papaioannou, D.; Waksman, G.; Caddick, S.; Baker, J. R. J. Am. Chem. Soc. 2010, 132, 1960-1965.
8. Li, F.; Allahverdi, A.; Yang, R.; Lua, G. B. J.; Zhang, X.; Cao, Y.; Korolev, N.; Nordenskiöld, L.; Liu, C.-F. Angew. Chem., Int. Ed. 2011, 50, 9611-9614.
9. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. Science 1994, 266, 776-779.
10. Dawson, P. E.; Kent, S. B. Annu. Rev. Biochem. 2000, 69, 923-960.
11. Geoghegan, K. F.; Stroh, J. G. Bioconjugate Chem. 1992, 3, 138-146.
12. Gilmore, J. M.; Scheck, R. A.; Esser-Kahn, A. P.; Joshi, N. S.; Francis, M. B. Angew. Chem., Int. Ed. 2006, 45, 5307-5311.
13. Obermeyer, A. C.; Jarman, J. B.; Francis, M. B. J. Am. Chem. Soc. 2014, 136, 9572-9579.
14. Dixon, H. B. F. J. Protein Chem. 1984, 3, 99-108.
15. Axup, J. Y.; Bajjuri, K. M.; Ritland, M.; Hutchins, B. M.; Kim, C. H.; Kazane, S. A.; Halder, R.; Forsyth, J. S.; Santidrian, A. F.; Stafin, K.; Lu, Y.; Tran, H.; Seller, A. J.; Biroc, S. L.; Szydlik, A.; Pinkstaff, J. K.; Tian, F.; Sinha, S. C.; Felding-Habermann, B.; Smider, V. V.; Schultz, P. G. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 16101-16106.
16. Lin, C.-W.; Ting, A. Y. J. Am. Chem. Soc. 2006, 128, 4542-4543.
17. Rashidian, M.; Dozier, J. K.; Distefano, M. D. Bioconjugate Chem. 2013, 24, 1277-1294.
18. Sletten, E. M.; Bertozzi, C. R. Angew. Chem., Int. Ed. 2009, 48, 6974-6998.
19. Witus, L. S.; Netirojjanakul, C.; Palla, K. S.; Muehl, E. M.; Weng, C. H.; Iavarone, A. T.; Francis, M. B. J. Am. Chem. Soc. 2013, 135, 17223-17229.
20. Jencks, W. P. J. Am. Chem. Soc. 1959, 81, 475-481.
21. Kalia, J.; Raines, R. T. Angew. Chem., Int. Ed. 2008, 47, 7523-7526.
22. Scheck, R. A.; Dedeo, M. T.; Iavarone, A. T.; Francis, M. B. J. Am. Chem. Soc. 2008, 130, 11762-11770.
23. Witus, L. S.; Francis, M. B. Curr. Protoc. Chem. Biol. 2010, 3, 1-10.
24. Hirel, P. H.; Schmitter, M. J.; Dessen, P.; Fayat, G.; Blanquet, S. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 8247-8251.
25. Yeoman, C. J.; Han, Y.; Dodd, D.; Schroeder, C. M.; Mackie, R. I.; Cann, I. K. O. Adv. Appl. Microbiol. 2010, 70, 1-55.
26. Mackenzie, K. J.; Francis, M. B. J. Am. Chem. Soc. 2013, 134, 293-300.
27. Ando, S.; Ishida, H.; Kosugi, Y.; Ishikawa, K. Appl. Environ. Microbiol. 2002, 68, 430-433.
28. Buckley, T. F.; Rapoport, H. J. Am. Chem. Soc. 1982, 104, 4446-4450.
29. Kim, H.-W.; Ishikawa, K. Proteins 2010, 78, 496-500.
30. Nagai, K.; Thogersen, H. C. Nature 1984, 309, 810-812.
31. Jenny, R. J.; Mann, K. G.; Lundblad, R. L. Protein Expression Purif. 2003, 31, 1-11.
32. Eliot, A. C.; Kirsch, J. F. Annu. Rev. Biochem. 2004, 73, 383-415.
33. Kataoka, M.; Ikemi, M.; Morikawa, T.; Miyoshi, T.; Nishi, K.; Wada, M. Eur. J. Biochem. 1997, 248, 385-393.
34. Kim, T. W.; Chokhawal, H. A.; Nadler, D.; Blanch, H. W.; Clark, D. S. Biotechnol. Bioeng. 2010, 107, 601-610.