Site-Selective Traceless Staudinger Ligation for Glycoprotein Synthesis Reveals Scope and Limitations

ChemBioChem

Volumn 12, Issue 9, 2011, Pages 1383-1386

  Bernardes, Gonçalo J L ^a   Linderoth, Lars ^a   Doores, Katie J ^a   Boutureira, Omar ^a   Davis, Benjamin G ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Glycoproteins; Protein modification; Staudinger ligation; Sugar phosphines

Indexed keywords

AMINO ACID; ASPARAGINE; AZIDE; BIOPOLYMER; GLYCOPROTEIN; PHOSPHINE;

ARTICLE; CATALYSIS; CONJUGATION; GLYCOPROTEIN SYNTHESIS; GLYCOSYLATION; HYDROLYSIS; PRIORITY JOURNAL; PROTEIN EXPRESSION; STAUDINGER REACTION;

AMINOBUTYRIC ACIDS; AZIDES; GLYCOPROTEINS; MOLECULAR STRUCTURE; PHOSPHINES; PROTEINS;

EID: 79958693812     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201100125     Document Type: Article

References (53)

1. B. G. Davis, Science 2004, 303, 480.
2. G. J. L. Bernardes, J. M. Chalker, B. G. Davis in Ideas in Chemistry and Molecular Sciences: Where Chemistry Meets Life (Ed.: B. Pignataro), Wiley-VCH, Weinheim, 2010, p. 59.
3. E. M. Sletten, C. R. Bertozzi, Angew. Chem. 2009, 121, 7108;
4. E. M. Sletten, C. R. Bertozzi, Angew. Chem. Int. Ed. 2009, 48, 6974.
5. C. P. R. Hackenberger, D. Schwarzer, Angew. Chem. 2008, 120, 10182.
6. B. G. Davis, Pure Appl. Chem. 2009, 81, 285.
7. K. L. Kiick, D. A. Tirrell, Tetrahedron 2000, 56, 9487.
8. C. C. Liu, P. G. Schultz, Annu. Rev. Biochem. 2010, 79, 413.
9. O. Boutureira, F. D'Hooge, M. Fernandez-Gonzalez, G. J. L. Bernardes, M. Sanchez-Navarro, J. R. Koeppe, B. G. Davis, Chem. Commun. 2010, 46, 8142.
10. S. I. van Kasteren, H. B. Kramer, H. H. Jensen, S. J. Campbell, J. Kirkpatrick, N. J. Oldham, D. C. Anthony, B. G. Davis, Nature 2007, 446, 1105.
11. J. Kalia, R. T. Raines, Curr. Org. Chem. 2010, 14, 138.
12. C. W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057.
13. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708;
14. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless,Angew. Chem. Int. Ed. 2002, 41, 2596.
15. N. J. Agard, J. A. Prescher, C. R. Bertozzi, J. Am. Chem. Soc. 2004, 126, 15046.
16. S. T. Laughlin, J. M. Baskin, S. L. Amacher, C. R. Bertozzi, Science 2008, 320, 664.
17. P. V. Chang, J. A. Prescher, E. M. Sletten, J. M. Baskin, I. A. Miller, N. J. Agard, A. Lo, C. R. Bertozzi, Proc. Natl. Acad. Sci. USA 2010, 107 1821.
18. X. Ning, J. Guo, M. A. Wolfert, G.-J. Boons, Angew. Chem. 2008, 120, 2285;
19. X. Ning, J. Guo, M. A. Wolfert, G.-J. Boons,Angew. Chem. Int. Ed. 2008, 47, 2253.
20. J. M. H. Staudinger, Helv. Chim. Acta 1919, 2, 635.
21. E. Saxon, C. R. Bertozzi, Science 2000, 287, 2007.
22. J. A. Prescher, D. H. Dube, C. R. Bertozzi, Nature 2004, 430, 873.
23. K. L. Kiick, E. Saxon, D. A. Tirrell, C. R. Bertozzi, Proc. Natl. Acad. Sci. USA 2002, 99, 19.
24. E. Saxon, J. I. Armstrong, C. R. Bertozzi, Org. Lett. 2000, 2, 2141.
25. B. L. Nilsson, L. L. Kiessling, R. T. Raines, Org. Lett. 2000, 2, 1939.
26. B. L. Nilsson, L. L. Kiessling, R. T. Raines, Org. Lett. 2001, 3, 9.
27. Y. He, R. J. Hinklin, J. Chang, L. L. Kiessling, Org. Lett. 2004, 6, 4479.
28. M. B. Soellner, B. L. Nilsson, R. T. Raines, J. Am. Chem. Soc. 2006, 128, 8820.
29. A. Bianchi, A. Russo, A. Bernardi, Tetrahedron: Asymmetry 2005, 16, 381.
30. A. Bianchi, A. Bernardi, J. Org. Chem. 2006, 71, 4565.
31. R. Kleineweischede, C. P. R. Hackenberger, Angew. Chem. 2008, 120, 6073;
32. R. Kleineweischede, C. P. R. Hackenberger,Angew. Chem. Int. Ed. 2008, 47, 5984.
33. C. Grandjean, A. Boutonnier, C. Guerreiro, J.-M. Fournier, L. A. Mulard, J. Org. Chem. 2005, 70, 7123.
34. M. L. Tsao, F. Tian, P. G. Schultz, ChemBioChem 2005, 6, 2147.
35. K. Ohtsubo, J. D. Marth, Cell 2006, 126, 855.
36. J. Coleman, L. Kirby, R. Klein, J. Lipid Res. 1995, 36, 901.
37. D. Fegley, S. Kathuria, R. Mercier, C. Li, A. Goutopoulos, A. Makriyannis, D. Piomelli, Proc. Natl. Acad. Sci. USA 2004, 101, 8756.
38. J. R. Rich, S. G. Withers, Nat. Chem. Biol. 2009, 5, 206.
39. M. Fernandez-Gonzalez, O. Boutureira, G. J. L. Bernardes, J. M. Chalker, M. A. Young, J. C. Errey, B. G. Davis, Chem. Sci. 2010, 709.
40. A. K. Sarkar, T. A. Fritz, W. H. Taylor, J. D. Esko, Proc. Natl. Acad. Sci. USA 1995, 92, 3323.
41. A. K. Sarkar, K. S. Rostand, R. K. Jain, K. L. Matta, J. D. Esko, J. Biol. Chem. 1997, 272, 25608.
42. O. Herd, A. Heβler, M. Hingst, P. Machnitzki, M. Tepper, O. Stelzer, Catal. Today 1998, 42, 413.
43. P. Phiasivongsa, J. Gallagher, C.-N. Chen, P. R. Jones, V. V. Samoshin, P. H. Gross, Org. Lett. 2002, 4, 4587.
44. W. Weiser, J. Lehmann, C. F. Brewer, E. J. Hehre, Carbohydr. Res. 1988, 183, 287.
45. C. F. Aguilar, I. Sanderson, M. Moracci, M. Ciaramella, R. Nucci, M. Rossi, L. H. Pearl, J. Mol. Biol. 1997, 271, 789.
46. M. W. Vetting, S. S. Hegde, K. Z. Hazleton, J. S. Blanchard, Protein Sci. 2007, 16, 755.
47. A similar ratio of reduction versus amide formation has been also observed by Schultz and co-workers when labelling a protein containing p-azidophenylalanine with a fluorophore; see ref. [30].
48. G. J. L. Bernardes, E. J. Grayson, S. Thompson, J. M. Chalker, J. C. Errey, F. E. Oualid, T. D. W. Claridge, B. G. Davis, Angew. Chem. 2008, 120, 2276;
49. G. J. L. Bernardes, E. J. Grayson, S. Thompson, J. M. Chalker, J. C. Errey, F. E. Oualid, T. D. W. Claridge, B. G. Davis,Angew. Chem. Int. Ed. 2008, 47, 2244.
50. D. Crich, V. Subramanian, M. Karatholuvhu, J. Org. Chem. 2009, 74, 9422.
51. Notably, the single report of selective functionalization of a protein containing an azide by using traceless Staudinger conditions was also performed in a Cys-free protein; see ref. [30].
52. M. B. Soellner, A. Tam, R. T. Raines, J. Org. Chem. 2006, 71, 9824.
53. A. Tam, M. B. Soellner, R. T. Raines, J. Am. Chem. Soc. 2007, 129, 11421.