Access to phosphoproteins and glycoproteins through semi-synthesis, Native Chemical Ligation and N→S acyl transfer

Organic and Biomolecular Chemistry

Volumn 8, Issue 22, 2010, Pages 5113-5119

  Masania, Jinit ^a   Li, Jiejin ^b   Smerdon, Stephen J ^b   MacMillan, Derek ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b NATIONAL INSTITUTE FOR MEDICAL RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACYL TRANSFER; BIOMOLECULAR PROCESS; GLYCOPEPTIDE SYNTHESIS; MODIFIED PROTEINS; NATIVE CHEMICAL LIGATION; PEPTIDE THIOESTERS; PHOSPHOPEPTIDES; PROTEIN SYNTHESIS; SEMISYNTHESIS; THIOESTERS;

PROTEINS;

SYNTHESIS (CHEMICAL);

CHECKPOINT KINASE 2; ESTER; GLYCOPROTEIN; NITROGEN; PEPTIDE; PHOSPHOPROTEIN; PROTEIN SERINE THREONINE KINASE; SULFUR;

ACYLATION; AMINO ACID SEQUENCE; ARTICLE; CHEMICAL MODEL; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; ISOLATION AND PURIFICATION; METABOLISM; MOLECULAR GENETICS; PROTEIN MULTIMERIZATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ACYLATION; AMINO ACID SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRYSTALLOGRAPHY, X-RAY; ESTERS; GLYCOPROTEINS; HUMANS; MODELS, CHEMICAL; MOLECULAR SEQUENCE DATA; NITROGEN; PEPTIDES; PHOSPHOPROTEINS; PROTEIN MULTIMERIZATION; PROTEIN-SERINE-THREONINE KINASES; SULFUR;

EID: 78049340012     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00363h     Document Type: Article

References (72)

1. J. A. Prescher C. R. Bertozzi Nat. Chem. Biol. 2005 1 13
2. G. A. Lemieux C. R. Bertozzi Trends Biotechnol. 1998 16 506
3. K. L. Kiick E. Saxon D. A. Tirrell C. R. Bertozzi Proc. Natl. Acad. Sci. U. S. A. 2002 99 19
4. X. Wu P. G. Schultz J. Am. Chem. Soc. 2009 131 12497
5. C. P. R. Hackenberger D. Schwarzer Angew. Chem., Int. Ed. 2008 47 10030
6. A. Dirksen P. E. Dawson Curr. Opin. Chem. Biol. 2008 12 760
7. P. E. Dawson T. W. Muir I. Clark-Lewis S. B. Kent Science 1994 266 776
8. G. G. Kochendoerfer S. B. H. Kent Curr. Opin. Chem. Biol. 1999 3 665
9. P. E. Dawson S. B. H. Kent Annu. Rev. Biochem. 2000 69 923
10. S. B. H. Kent Chem. Soc. Rev. 2009 38 338 351
11. H. D. Mootz ChemBioChem 2009 10 2579
12. J. A. Camarero D. Fushman D. Cowburn T. W. Muir Bioorg. Med. Chem. 2001 9 2479
13. I. Giriat T. W. Muir J. Am. Chem. Soc. 2003 125 7180
14. S. W. Lockless T. W. Muir Proc. Natl. Acad. Sci. U. S. A. 2009 106 10999
15. C. Chatterjee Robert K. McGinty J.-P. Pellois T. W. Muir Angew. Chem., Int. Ed. 2007 46 2814
16. C. Chatterjee T. W. Muir J. Biol. Chem. 2010 285 11045
17. R. R. Flavell M. Huse M. Goger M. Trester-Zedlitz J. Kuriyan T. W. Muir Org. Lett. 2002 4 165
18. M. Huse M. N. Holford J. Kuriyan T. W. Muir J. Am. Chem. Soc. 2000 122 8337
19. L. A. Marcaurelle L. S. Mizoue J. Wilken L. Oldham S. B. H. Kent T. M. Handel C. R. Bertozzi Chem.-Eur. J. 2001 7 1129
20. K. A. Winans D. S. King V. R. Rao C. R. Bertozzi Biochemistry 1999 38 11700
21. Y. Shin K. A. Winans B. J. Backes S. B. H. Kent J. A. Ellman C. R. Bertozzi J. Am. Chem. Soc. 1999 121 11684
22. D. Macmillan Angew. Chem., Int. Ed. 2006 45 7668 7672
23. J. Offer C. N. C. Boddy P. E. Dawson J. Am. Chem. Soc. 2002 124 4642
24. F. Burlina D. D. Dixson R. P. Doyle G. Chassaing C. N. Boddy P. Dawson J. Offer Chem. Commun. 2008 2785
25. P. Botti M. R. Carrasco S. B. H. Kent Tetrahedron Lett. 2001 42 1831
26. D. Macmillan D. W. Anderson Org. Lett. 2004 6 4659
27. W. Qian S. J. Danishefsky Angew. Chem., Int. Ed. 2007 46 9248
28. J. Chen Q. Wan Y. Yuan J. Zhu S. J. Danishefsky Angew. Chem., Int. Ed. 2008 47 8521
29. J. Chen P. Wang J. Zhu Q. Wan S. J. Danishefsky Tetrahedron 2010 66 2277
30. C. Kan S. J. Danishefsky Tetrahedron 2009 65 9047
31. D. Crich A. Banerjee J. Am. Chem. Soc. 2007 129 10064
32. C. Haase H. Rohde O. Seitz Angew. Chem., Int. Ed. 2008 47 6807
33. R. Okamoto Y. Kajihara Angew. Chem., Int. Ed. 2008 47 5402
34. J. Kang D. Macmillan Org. Biomol. Chem. 2010 8 1993 2002
35. J. Kang J. P. Richardson D. Macmillan Chem. Commun. 2009 407
36. J. Kang N. L. Reynolds C. Tyrrell J. R. Dorin D. Macmillan Org. Biomol. Chem. 2009 7 4918
37. J. P. Richardson C.-H. Chan J. Blanc M. Saadi D. Macmillan Org. Biomol. Chem. 2010 8 1351
38. R. J. Payne C.-H. Wong Chem. Commun. 2010 46 21
39. D. P. Gamblin S. I. v. Kasteren J. M. Chalker B. G. Davis FEBS J. 2008 275 1949
40. 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
41. R. G. Spiro Glycobiology 2002 12 43R 56R
42. B. Wu J. Chen J. D. Warren G. Chen Z. Hua S. J. Danishefsky Angew. Chem., Int. Ed. 2006 45 4116
43. G. Chen Q. Wan Z. Tan C. Kan Z. Hua K. Ranganathan S. J. Danishefsky Angew. Chem., Int. Ed. 2007 46 7383
44. P. Nagorny B. Fasching X. Li G. Chen B. Aussedat S. J. Danishefsky J. Am. Chem. Soc. 2009 131 5792
45. Z. Tan S. Shang T. Halkina Y. Yuan S. J. Danishefsky J. Am. Chem. Soc. 2009 131 5424 5431
46. P. H. Seeberger Nat. Chem. Biol. 2009 5 368
47. G. a. J. L. Bernardes B. Castagner P. H. Seeberger ACS Chem. Biol. 2009 4 703
48. T. J. Boltje T. Buskas G.-J. Boons Nat. Chem. 2009 1 611
49. D. P. Gamblin E. M. Scanlan B. G. Davis Chem. Rev. 2009 109 131
50. S. R. Hamilton T. U. Gerngross Curr. Opin. Biotechnol. 2007 18 387
51. F. Schwarz W. Huang C. Li B. L. Schulz C. Lizak A. Palumbo S. Numao D. Neri M. Aebi L.-X. Wang Nat. Chem. Biol. 2010 6 264
52. D. Macmillan C. R. Bertozzi Angew. Chem., Int. Ed. 2004 43 1355
53. C. P. R. Hackenberger C. T. Friel S. E. Radford B. Imperiali J. Am. Chem. Soc. 2005 127 12882
54. H. Hojo Y. Matsumoto Y. Nakahara E. Ito Y. Suzuki M. Suzuki A. Suzuki Y. Nakahara J. Am. Chem. Soc. 2005 127 13720
55. N. Yamamoto Y. Tanabe R. Okamoto P. E. Dawson Y. Kajihara J. Am. Chem. Soc. 2008 130 501
56. C. Piontek P. Ring O. Harjes C. Heinlein S. Mezzato N. Lombana C. Pöhner M. Püttner D. V. Silva A. Martin Franz X. Schmid C. Unverzagt Angew. Chem., Int. Ed. 2009 48 1936
57. C. Piontek D. V. Silva C. Heinlein C. Pöhner S. Mezzato P. Ring A. Martin Franz X. Schmid C. Unverzagt Angew. Chem., Int. Ed. 2009 48 1941
58. T. W. Muir D. Sondhi P. A. Cole Proc. Natl. Acad. Sci. U. S. A. 1998 95 6705
59. J.-P. Pellois T. W. Muir Curr. Opin. Chem. Biol. 2006 10 487
60. D. Macmillan L. Arham J. Am. Chem. Soc. 2004 126 9530
61. T. J. Tolbert C.-H. Wong Angew. Chem., Int. Ed. 2002 41 2171
62. G. K. Busch E. W. Tate P. R. J. Gaffney E. Rosivatz R. Woscholski R. J. Leatherbarrow Chem. Commun. 2008 3369
63. B. L. Pentelute A. P. Barker B. E. Janowiak S. B. H. Kent R. J. Collier ACS Chem. Biol. 2010 5 359
64. D. Macmillan C. R. Bertozzi Angew. Chem., Int. Ed. 2004 43 1355
65. S. Matsuoka M. Huang S. J. Elledge Science 1998 282 1893
66. V. V. Rostovtsev L. G. Green V. V. Fokin K. B. Sharpless Angew. Chem., Int. Ed. 2002 41 2596
67. M. Meldal C. W. Tornøe Chem. Rev. 2008 108 2952
68. M. R. Pratt C. R. Bertozzi J. Am. Chem. Soc. 2003 125 6149
69. A. B. Diekman E. J. Norton K. L. Klotz V. A. Westbrook J. C. Herr Immunol. Rev. 1999 171 203
70. In our hands glycine thioesters appear particularly prone to hydrolysis and as much and 5% hydrolysed product was recovered. In general, very little hydrolysis is observed over a 48 h period.
71. Z. Cai N. H. Chehab N. P. Pavletich Mol. Cell 2009 35 818 829
72. J. Li I. A. Taylor J. Lloyd J. A. Clapperton S. Howell D. MacMillan S. J. Smerdon J. Biol. Chem. 2008 283 36019 36030