Mild bioconjugation through the oxidative coupling of ortho-aminophenols and anilines with ferricyanide

Angewandte Chemie - International Edition

Volumn 53, Issue 4, 2014, Pages 1057-1061

  Obermeyer, Allie C ^a   Jarman, John B ^a   Netirojjanakul, Chawita ^a   El Muslemany, Kareem ^a   Francis, Matthew B ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

amines; bioconjugation; iron; oxidation; proteins

Indexed keywords

1 ,2-DIOLS; BIO-CONJUGATION; BIOCONJUGATES; EFFICIENT COUPLING; MILD OXIDANTS; MODIFIED PROTEINS; OXIDATIVE COUPLINGS; PROTEIN SUBSTRATE;

AMINES; IRON; MOLECULES; OXIDANTS; OXIDATION; PROTEINS;

ANILINE;

2 AMINOPHENOL; 2-AMINOPHENOL; AMINE; AMINOPHENOL DERIVATIVE; ANILINE; ANILINE DERIVATIVE; FERRICYANIDE; IRON; PROTEIN;

ARTICLE; BIOCONJUGATION; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION; OXIDATION REDUCTION REACTION;

AMINES; BIOCONJUGATION; IRON; OXIDATION; PROTEINS;

AMINOPHENOLS; ANILINE COMPOUNDS; FERRICYANIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 84893259496     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201307386     Document Type: Article

References (50)

1. H. M. O'Hare, K. Johnsson, A. Gautier, Curr. Opin. Struct. Biol. 2007, 17, 488-494.
2. S. Zalipsky, Bioconjugate Chem. 1995, 6, 150-165.
3. S. C. Alley, N. M. Okeley, P. D. Senter, Curr. Opin. Chem. Biol. 2010, 14, 529-537.
4. W. Wu, S. C. Hsiao, Z. M. Carrico, M. B. Francis, Angew. Chem. 2009, 121, 9657-9661
5. Angew. Chem. Int. Ed. 2009, 48, 9493-9497
6. N. Stephanopoulos, G. J. Tong, S. C. Hsiao, M. B. Francis, ACS Nano 2010, 4, 6014-6020.
7. J. J. Day, B. V. Marquez, H. E. Beck, T. A. Aweda, P. D. Gawande, C. F. Meares, Curr. Opin. Chem. Biol. 2010, 14, 803-809
8. G. J. Tong, S. C. Hsiao, Z. M. Carrico, M. B. Francis, J. Am. Chem. Soc. 2009, 131, 11174-11178.
9. E. Baslé, N. Joubert, M. Pucheault, Chem. Biol. 2010, 17, 213-227
10. E. M. Sletten, C. R. Bertozzi, Angew. Chem. 2009, 121, 7108-7133
11. Angew. Chem. Int. Ed. 2009, 48, 6974-6998
12. C. H. Kim, J. Y. Axup, P. G. Schultz, Curr. Opin. Chem. Biol. 2013, 17, 412-419
13. M. F. Debets, J. C. M. van Hest, F. P. J. T. Rutjes, Org. Biomol. Chem. 2013, 11, 6439-6455
14. Y. Takaoka, A. Ojida, I. Hamachi, Angew. Chem. 2013, 125, 4182-4200
15. Angew. Chem. Int. Ed. 2013, 52, 4088-4106.
16. M. W. Crankshaw, G. A. Grant, in Current Protocols in Protein Science (Eds.:, J. E. Coligan, B. M. Dunn, H. L. Ploegh, D. W. Speicher, P. T. Wingfield,), Wiley, New York, 2001, pp. 15.1.1-15.1.18
17. J. M. Chalker, G. J. L. Bernardes, Y. A. Lin, B. G. Davis, Chem. Asian J. 2009, 4, 630-640.
18. H. C. Hang, C. Yu, D. L. Kato, C. R. Bertozzi, Proc. Natl. Acad. Sci. USA 2003, 100, 14846-14851.
19. V. W. Cornish, K. M. Hahn, P. G. Schultz, J. Am. Chem. Soc. 1996, 118, 8150-8151
20. A. Dirksen, P. E. Dawson, Bioconjugate Chem. 2008, 19, 2543-2548.
21. K. L. Kiick, E. Saxon, D. A. Tirrell, C. R. Bertozzi, Proc. Natl. Acad. Sci. USA 2002, 99, 19-24
22. J. C. Jewett, C. R. Bertozzi, Chem. Soc. Rev. 2010, 39, 1272-1279.
23. M. L. Blackman, M. Royzen, J. M. Fox, J. Am. Chem. Soc. 2008, 130, 13518-13519
24. N. K. Devaraj, R. Weissleder, S. A. Hilderbrand, Bioconjugate Chem. 2008, 19, 2297-2299.
25. N. Li, R. K. V. Lim, S. Edwardraja, Q. Lin, J. Am. Chem. Soc. 2011, 133, 15316-15319.
26. C. R. Behrens, J. M. Hooker, A. C. Obermeyer, D. W. Romanini, E. M. Katz, M. B. Francis, J. Am. Chem. Soc. 2011, 133, 16398-16401.
27. L. S. Witus, M. B. Francis, Acc. Chem. Res. 2011, 44, 774-783.
28. R. A. Miller, A. D. Presley, M. B. Francis, J. Am. Chem. Soc. 2007, 129, 3104-3109
29. M. T. Dedeo, K. E. Duderstadt, J. M. Berger, M. B. Francis, Nano Lett. 2010, 10, 181-186.
30. A. P. Esser-Kahn, A. T. Iavarone, M. B. Francis, J. Am. Chem. Soc. 2008, 130, 15820-15822.
31. J. M. Hooker, E. W. Kovacs, M. B. Francis, J. Am. Chem. Soc. 2004, 126, 3718-3719
32. J. M. Hooker, A. P. Esser-Kahn, M. B. Francis, J. Am. Chem. Soc. 2006, 128, 15558-15559.
33. L. Wang, A. Brock, B. Herberich, P. G. Schultz, Science 2001, 292, 498-500
34. R. A. Mehl, J. C. Anderson, S. W. Santoro, L. Wang, A. B. Martin, D. S. King, D. M. Horn, P. G. Schultz, J. Am. Chem. Soc. 2003, 125, 935-939
35. Z. M. Carrico, D. W. Romanini, R. A. Mehl, M. B. Francis, Chem. Commun. 2008, 1205.
36. J. H. Strauss, Jr., R. L. Sinsheimer, J. Mol. Biol. 1963, 7, 43-54
37. K. Valegård, L. Liljas, K. Fridborg, T. Unge, Nature 1990, 345, 36-41.
38. E. Antonini, M. Brunori, J. Wyman, Biochemistry 1965, 4, 545-551
39. J. F. Corbett, J. Chem. Soc. B 1969, 207-212
40. S. Gardlik, K. V. Rajagopalan, J. Biol. Chem. 1991, 266, 4889-4895
41. Y. Yamagishi, H. Ashigai, Y. Goto, H. Murakami, H. Suga, ChemBioChem 2009, 10, 1469-1472.
42. L. P. Hadjipetrou, T. Gray-Young, M. D. Lilly, J. Gen. Microbiol. 1966, 45, 479-488
43. C. Liu, T. Sun, Y. Zhai, S. Dong, Talanta 2009, 78, 613-617.
44. S. C. Alley, K. E. Anderson, Curr. Opin. Chem. Biol. 2013, 17, 406-411
45. J. Caravella, A. Lugovskoy, Curr. Opin. Chem. Biol. 2010, 14, 520-528.
46. J. K. Hamilton, F. Smith, J. Am. Chem. Soc. 1956, 78, 5910-5912.
47. C. Netirojjanakul, L. S. Witus, C. R. Behrens, C.-H. Weng, A. T. Iavarone, M. B. Francis, Chem. Sci. 2013, 4, 266-272.
48. J. M. Gilmore, R. A. Scheck, A. P. Esser-Kahn, N. S. Joshi, M. B. Francis, Angew. Chem. 2006, 118, 5433-5437
49. Angew. Chem. Int. Ed. 2006, 45, 5307-5311
50. L. S. Witus, T. Moore, B. W. Thuronyi, A. P. Esser-Kahn, R. A. Scheck, A. T. Iavarone, M. B. Francis, J. Am. Chem. Soc. 2010, 132, 16812-16817.