Sugar-assisted glycopeptide ligation with complex oligosaccharides: Scope and limitations

Journal of the American Chemical Society

Volumn 130, Issue 36, 2008, Pages 11945-11952

  Bennett, Clay S ^a   Dean, Stephen M ^a   Payne, Richard J ^a,c   Ficht, Simon ^a   Brik, Ashraf ^a,d   Wong, Chi Huey ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b GENOMICS RESEARCH CENTER   (Taiwan)

^c UNIVERSITY OF SYDNEY   (Australia)

^d BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; COMPLEXATION; GLUCOSE; GLYCOPROTEINS; GLYCOSYLATION; PEPTIDES; PORT TERMINALS; PROTEINS; SUGAR (SUCROSE);

GLYCOPEPTIDES; N TERMINALS;

SUGARS;

GLYCAN; GLYCOPEPTIDE; GLYCOPROTEIN; MONOSACCHARIDE; OLIGOSACCHARIDE; THIOESTER; THIOL;

AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL REACTION; COMPLEX FORMATION; GLYCOSYLATION; PEPTIDE SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS; SUGAR ASSISTED LIGATION;

ACETYLGALACTOSAMINE; ACETYLGLUCOSAMINE; AMINO ACIDS; GLYCOPEPTIDES; GLYCOSYLATION; GLYCOSYLTRANSFERASES; OLIGOSACCHARIDES; POLYSACCHARIDES; SULFHYDRYL COMPOUNDS;

EID: 51749114233     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8010513     Document Type: Article

References (64)

1. Apweiler, R.; Hermjakob, H.; Sharon, N. Biochem. Biophys. Acta 1999, 1473, 4-8.
2. Spiro, R. G. Glycobiology 2002, 12, 43R-56R.
3. Sita, R.; Braakman, I. Nature 2003, 426, 891-894.
4. Spiro, R. G. Cell. Mol. Life Sci. 2004, 61, 1025-1041.
5. Helenius, A.; Aebi, M. Annu. Rev. Biochem. 2004, 73, 1019-1049.
6. Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
7. Varki, A. Glycobiology 1993, 3, 97-130.
8. Miller, L. H.; Good, M. F.; Milon, G. Science 1994, 264, 1878-1883.
9. Dube, D. H.; Bertozzi, C. R. Nat. Rev. Drug. Discovery 2005, 4, 477- 488.
10. David, B. G. Chem. Rev. 2002, 102, 579-601.
11. Pratt, M. R.; Bertozzi, C. R. Chem. Soc. Rev. 2005, 34, 58-68.
12. Bennett, C. S.; Wong, C. H. Chem. Soc. Rev. 2007, 36, 1227-1238.
13. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779.
14. Dawson, P. E.; Kent, S. B. H. Annu. Rev. Biochem. 2000, 69, 923-960.
15. Shin, Y.; Winans, K. A.; Backes, B. J.; Kent, S. B. H.; Ellman, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 1999, 121, 11684-11689.
16. Marcaurelle, L. A.; Mizoue, L. S.; Wilken, J.; Oldham, L.; Kent, S. B. H.; Handel, T. M.; Bertozzi, C. R. Chem. - Eur. J. 2001, 7, 1129-1132.
17. Warren, J. D.; Miller, J. S.; Keding, S. J.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 6576-6578.
18. Mezzato, S.; Schaffrath, M.; Schaffrath, M.; Unverzagt, C. Angew. Chem., Int. Ed. 2005, 44, 1650-1654.
19. Hackenberger, C. P. R.; Friel, C. T.; Radford, S. E.; Imperiali, B. J. Am. Chem. Soc. 2005, 127, 12882-12889.
20. Chen, J.; Chen, G.; Wu, B.; Wan, Q.; Tan, Z.; Hua, Z.; Danishefsky, S. J. Tetrahedron Lett. 2006, 8013-8016.
21. Yamamoto, N.; Tanabe, Y.; Okamoto, R; Dawson, P. E.; Kajihara, Y. J. Am. Chem. Soc. 2008, 130, 501-510.
22. Yan, L. Z.; Dawson, P. E. J. Am. Chem. Soc. 2001, 123, 526-533.
23. Pentlute, B. L.; Kent, S. B. H. Org. Lett. 2007, 9, 687-690.
24. Crich, D.; Banerjee, A. J. Am. Chem. Soc. 2007, 129, 10064-10065.
25. Offer, J.; Boddy, C. N. C.; Dawson, P. E. J. Am. Chem. Soc. 2002, 124, 4642-4646.
26. Low, D. W.; Hill, M. G.; Carrasco, M. R.; Kent, S. B. H.; Botti, P. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 6554-6559.
27. Macmillan, D.; Anderson, D. W. Org. Lett. 2004, 6, 4659-4125.
28. Wu, B.; Chen, J. H.; Warren, J. D.; Chen, G.; Hua, Z. H.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2006, 45, 4116-4125.
29. Macmillan, D. Angew. Chem., Int. Ed. 2006, 45, 7668-7672.
30. Chen, G.; Warren, J. D.; Chen, J.; Wu, B.; Wan, Q.; Danishefsky, S. J. J. Am. Chem. Soc. 2006, 128, 7460-7462.
31. Brik, A.; Yang, Y. Y.; Ficht, S.; Wong, C. H. J. Am. Chem. Soc. 2006, 128, 5626-5627.
32. Brik, A.; Ficht, S.; Yang, Y. Y.; Bennett, C. S.; Wong, C. H. J. Am. Chem. Soc. 2006, 128, 15026-15033.
33. Ficht, S.; Payne, R. J.; Brik, A.; Wong, C. H. Angew. Chem., Int. Ed. 2007, 46, 5975-5979.
34. Payne, R. J.; Ficht, S.; Tang, S.; Brik, A.; Yang, Y. Y.; Wong, C. H. J. Am. Chem. Soc. 2007, 129, 13527-13536.
35. Brik, A.; Wong, C. H. Chem. - Eur. J. 2007, 13, 5670-5675.
36. Yang, Y. Y.; Ficht, S.; Brik, A.; Wong, C. H. J. Am. Chem. Soc. 2007, 129, 7690-7701.
37. Wan, Q.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2007, 46, 9248-9252.
38. Hsieh-Wilson, L. Nature 2007, 445, 31-33.
39. For a recent example where enzymatic elaboration of a glycopeptide containing two N-acetylglucosamine residues led to mixtures of products, see: (a) Haneda, K.; Takeuchi, M.; Tagashira, M.; Inazu, T.; Toma, K.; Isogai, Y.; Hori, M.; Kobayashi, K.; Takeuchi, M.; Takegawa, K.; Yamamoto, K. Carbohydr. Res. 2004, 341, 181-190.
40. Paulsen, H.; Krogmann, C. Liebigs Ann. Chem. 1989, 1203-1213.
41. Dejter-Juszynski, D.; Flowers, H. M. Carboydr. Res. 1971, 18, 215-226.
42. Lemieux, R. U.; Hendriks, K. B.; James; Stick, R. V.; James, K. J. Am. Chem. Soc. 1975, 97, 4056-4062.
43. For the use of halide-ion-mediated glycosylation on a similar system, see: (a) Lee, H. H.; Baptista, J. A. B.; Krepinsky, J. J. Can. J. Chem. 1990, 68, 953-957.
44. Schmidt, R. R.; Michel, J. Tetrahedron Lett. 1984, 25, 821-824.
45. Vorheer, T.; Bannwarth, W. Bioorg. Med. Chem. Lett. 1995, 5, 2661-2664.
46. Kupihar, Z.; Schmel, Z.; Kele, Z.; Penke, B.; Kovacs, L. Bioorg. Med. Chem. Lett. 2001, 9, 1241-1247.
47. Ciommer, M.; Kunz, H. Synlett 1991, 8, 593-595.
48. Albericio, F.; Carpino, L. A. Methods Enzymol. 1997, 289, 104-126.
49. Brocke, C.; Kunz, H. Synthesis 2004, 525-542.
50. Kemp, D. S.; Bernstein, Z. W.; McNiel, G. N. J. Org. Chem. 1974, 39, 2831-2835.
51. Kemp, D. S.; Choone, S. L. H.; Pekaar, J. J. Org. Chem. 1974, 39, 3841-3847.
52. Payne, R. J.; Ficht, S.; Greenberg, W. A.; Wong, C. H. Angew. Chem., Int. Ed. 2008, 47, 4411-4415.
53. Blixt, O.; Razi, N. Methods Enzymol. 2006, 415, 4411-4415.
54. Schanbacher, F. L.; Ebner, K. E. J. Biol. Chem. 1970, 245, 5057-5061.
55. Beyer, T. A.; Sadler, J. E.; Rearicj, J. I.; Paulson, J. C.; Hill, R. L. Adv. Enzymol. 1981, 52, 23-175.
56. Wen, D. X.; Livingston, B. D.; Medzihradszky, K. F.; Kelm, S.; Burlingame, A. L.; Paulson, J. C. J. Biol. Chem. 1992, 267, 21011-21019.
57. Wen, D. X.; Livingston, B. D.; Medzihradszky, K. F.; Keim, S.; Burlingame, A. L.; Paulson, J. C. J. Biol. Chem. 1992, 267, 21011-21019.
58. Lin, S. W.; Yuan, T. M.; Li, J. R.; Lin, C. H. Biochemistry 2006, 45, 8108-8116.
59. Fan, J. Q.; Takegawa, K.; Iwahara, S.; Kondo, A.; Kato, I.; Abeyunawardana, C.; Lee, Y. C. J. Biol. Chem. 1995, 270, 17723-17729.
60. Akaike, E.; Tsutsumida, M.; Osumi, K.; Fujita, M.; Yamanoi, T.; Yamamoto, K.; Fujta, K. Carbohydr. Res. 2004, 339, 719-722.
61. Li, B.; Zeng, Y.; Hauser, S.; Song, H.; Wang, L. X. J. Am. Chem. Soc. 2005, 127, 9692-9693.
62. Li, H.; Li, B.; Song, H.; Breydo, L.; Baskakov, I. V.; Wag, L. X. J. Org. Chem. 2005, 70, 9990-9996.
63. Zeng, Y.; Wang, J.; Li, B.; Hauser, S.; Li, H.; Wang, L. X. Chem. - Eur. J. 2006, 12, 3355-3364.
64. Rising, T. W. D. F.; Claridge, T. D. W.; Moir, J. W. B.; Fairbanks, A. J. ChemBioChem 2006, 7, 1177-1180.