Self-liganded Suzuki-Miyaura coupling for site-selective protein PEGylation

Angewandte Chemie - International Edition

Volumn 52, Issue 14, 2013, Pages 3916-3921

  Dumas, Anaëlle ^a   Spicer, Christopher D ^a   Gao, Zhanghua ^a   Takehana, Tsuyoshi ^b   Lin, Yuya A ^a   Yasukohchi, Tohru ^b   Davis, Benjamin G ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b NOF Corporation   (Japan)

Author keywords

catalysis; PEGylation; proteins; Suzuki Miyaura coupling

Indexed keywords

EXOGENOUS LIGANDS; NON NATURAL AMINO ACIDS; PEGYLATION; PROTEIN PEGYLATION; SITE SELECTIVE; SUZUKI-MIYAURA COUPLING;

AMINO ACIDS; CATALYSIS; EXCITONS; PROTEINS;

CHEMICAL REACTIONS;

BORONIC ACID DERIVATIVE; MACROGOL DERIVATIVE; PALLADIUM; PROTEIN;

ARTICLE; CATALYSIS; CHEMISTRY; METABOLISM;

BORONIC ACIDS; CATALYSIS; PALLADIUM; POLYETHYLENE GLYCOLS; PROTEINS;

EID: 84875733018     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201208626     Document Type: Article

References (59)

1. S. L. Buchwald, Acc. Chem. Res. 2008, 41, 1439-1439
2. M. R. Huang, P. Gao, X. G. Li, Huaxue Jinzhan 2010, 22, 113-118
3. A. de Meijere, F. Diederich, Metal-catalyzed cross-coupling reactions, 2 nd ed., Wiley-VCH, Weinheim, 2004
4. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483
5. Y. Nakama, O. Yoshida, M. Yoda, K. Araki, Y. Sawada, J. Nakamura, S. Xu, K. Miura, H. Maki, H. Arimoto, J. Med. Chem. 2010, 53, 2528-2533
6. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516-4563
7. Angew. Chem. Int. Ed. 2005, 44, 4442-4489
8. E. Perissutti, F. Frecentese, A. Lavecchia, F. Fiorino, B. Severino, F. De Angelis, V. Santagada, G. Caliendo, Tetrahedron 2007, 63, 12779-12785
9. J. Sakamoto, M. Rehahn, G. Wegner, A. D. Schlüter, Macromol. Rapid Commun. 2009, 30, 653-687
10. R. Severinsen, G. T. Bourne, T. T. Tran, M. Ankersen, M. Begtrup, M. L. Smythe, J. Comb. Chem. 2008, 10, 557-566.
11. J. M. Chalker, C. S. C. Wood, B. G. Davis, J. Am. Chem. Soc. 2009, 131, 16346-16347
12. C. D. Spicer, B. G. Davis, Chem. Commun. 2011, 47, 1698-1700
13. Y. S. Wang, W. K. Russell, Z. Y. Wang, W. Wan, L. E. Dodd, P. J. Pai, D. H. Russell, W. S. R. Liu, Mol. BioSyst. 2011, 7, 714-717
14. N. Li, R. K. V. Lim, S. Edwardraja, Q. Lin, J. Am. Chem. Soc. 2011, 133, 15316-15319
15. C. D. Spicer, T. Triemer, B. G. Davis, J. Am. Chem. Soc. 2012, 134, 800-803
16. J. Li, P. R. Chen, ChemBioChem 2012, 13, 1728-1731.
17. C. C. Liu, P. G. Schultz, Annu. Rev. Biochem. 2010, 79, 413-444.
18. J. M. Chalker, G. J. L. Bernardes, B. G. Davis, Acc. Chem. Res. 2011, 44, 730-741.
19. S. N. S. Alconcel, A. S. Baas, H. D. Maynard, Polym. Chem. 2011, 2, 1442-1448
20. S. Jevševar, M. Kunstelj, V. G. Porekar, Biotechnol. J. 2010, 5, 113-128
21. F. M. Veronese, A. Mero, G. Pasut, in PEGylated protein drugs: Basic science and clinical applications (Ed.:, F. Veronese,), Birkhäuser, Basel, 2009, pp. 11-31.
22. A. Deiters, T. A. Cropp, D. Summerer, M. Mukherji, P. G. Schultz, Bioorg. Med. Chem. Lett. 2004, 14, 5743-5745
23. A. J. Keefe, S. Y. Jiang, Nat. Chem. 2012, 4, 59-63.
24. S. Balan, J.-W. Choi, A. Godwin, I. Teo, C. M. Laborde, S. Heidelberger, M. Zloh, S. Shaunak, S. Brocchini, Bioconjugate Chem. 2006, 18, 61-76
25. G. M. Bonora, S. Drioli, in Protein PEGylation, basic science and biological applications (Ed.:, F. Veronese,), Birkhäuser, Basel, 2009, pp. 33-45
26. M. A. Gauthier, H.-A. Klok, Chem. Commun. 2008, 2591-2611
27. O. Kinstler, G. Molineux, M. Treuheit, D. Ladd, C. Gegg, Adv. Drug Delivery Rev. 2002, 54, 477-485
28. H.-A. Klok, Macromolecules 2009, 42, 7990-8000
29. M. J. Roberts, M. D. Bentley, J. M. Harris, Adv. Drug Delivery Rev. 2002, 54, 459-476
30. S. Shaunak, A. Godwin, J.-W. Choi, S. Balan, E. Pedone, D. Vijayarangam, S. Heidelberger, I. Teo, M. Zloh, S. Brocchini, Nat. Chem. Biol. 2006, 2, 312-313.
31. C. J. Fee, J. A. VanAlstine, Chem. Eng. Sci. 2006, 61, 924-939.
32. R. Serwa, P. Majkut, B. Horstmann, J.-M. Swiecicki, M. Gerrits, E. Krause, C. P. R. Hackenberger, Chem. Sci. 2010, 1, 596-602.
33. L. A. Adrio, B. N. Nguyen, G. Guilera, A. G. Livingston, K. K. Hii, Catal. Sci. Technol. 2012, 2, 316-323
34. C. Torborg, M. Beller, Adv. Synth. Catal. 2009, 351, 3027-3043
35. R. Franzén, Y. J. Xu, Can. J. Chem. 2005, 83, 266-272
36. G. A. Molander, B. Biolatto, J. Org. Chem. 2003, 68, 4302-4314.
37. A. Arcadi, G. Cerichelli, M. Chiarini, M. Correa, D. Zorzan, Eur. J. Org. Chem. 2003, 4080-4086
38. C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, J. Org. Chem. 1999, 64, 3885-3890
39. W. Han, C. Liu, Z.-L. Jin, Org. Lett. 2007, 9, 4005-4007
40. W. Han, C. Liu, Z.-L. Jin, Adv. Synth. Catal. 2008, 350, 501-508
41. J.-H. Li, W.-J. Liu, Y.-X. Xie, J. Org. Chem. 2005, 70, 5409-5412
42. L. Liu, Y. Zhang, Y. Wang, J. Org. Chem. 2005, 70, 6122-6125
43. V. V. Namboodiri, R. S. Varma, Green Chem. 2001, 3, 146-148
44. T. M. Razler, Y. Hsiao, F. Qian, R. Fu, R. K. Khan, W. Doubleday, J. Org. Chem. 2009, 74, 1381-1384.
45. S. Li, Y. Lin, J. Cao, S. Zhang, J. Org. Chem. 2007, 72, 4067-4072.
46. M. Moreno-Mañas, M. Pérez, R. Pleixats, J. Org. Chem. 1996, 61, 2346-2351.
47. A. D. Chowdhury, S. M. Mobin, S. Mukherjee, S. Bhaduri, G. K. Lahiri, Eur. J. Inorg. Chem. 2011, 3232-3239.
48. M. W. Vetting, S. S. Hegde, K. Z. Hazleton, J. S. Blanchard, Protein Sci. 2007, 16, 755-760.
49. T. S. Young, I. Ahmad, J. A. Yin, P. G. Schultz, J. Mol. Biol. 2010, 395, 361-374.
50. M. R. Stabile, W. G. Lai, G. DeSantis, M. Gold, J. B. Jones, Bioorg. Med. Chem. Lett. 1996, 6, 2501-2506.
51. F.-Y. Jeng, S.-C. Lin, Process Biochem. 2006, 41, 1566-1573.
52. A. C. French, A. L. Thompson, B. G. Davis, Angew. Chem. 2009, 121, 1274-1278
53. Angew. Chem. Int. Ed. 2009, 48, 1248-1252.
54. Y. Yamamoto, M. Takizawa, X.-Q. Yu, N. Miyaura, Angew. Chem. 2008, 120, 942-945
55. Angew. Chem. Int. Ed. 2008, 47, 928-931
56. K. L. Billingsley, S. L. Buchwald, Angew. Chem. 2008, 120, 4773-4776
57. Angew. Chem. Int. Ed. 2008, 47, 4695-4698
58. H. Bonin, D. Delbrayelle, P. Demonchaux, E. Gras, Chem. Commun. 2010, 46, 2677-2679.
59. C. E. Garrett, K. Prasad, Adv. Synth. Catal. 2004, 346, 889-900.