Sortase A-catalyzed transpeptidation of glycosylphosphatidylinositol derivatives for chemoenzymatic synthesis of GPI-anchored proteins

Journal of the American Chemical Society

Volumn 132, Issue 5, 2010, Pages 1567-1571

  Wu, Zhimeng ^a   Guo, Xueqing ^a   Wang, Qianli ^a   Swarts, Benjamin M ^a   Guo, Zhongwu ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C-TERMINUS; CHEMO-ENZYMATIC SYNTHESIS; GLYCINE RESIDUES; GLYCOPEPTIDES; GLYCOSYLPHOSPHATIDYLINOSITOL; GPI-ANCHORED PROTEIN; PHOSPHOETHANOLAMINE; SORTASE; SORTING SIGNALS; STERIC HINDRANCES; SYNTHETIC STRATEGIES;

GLUCOSE; GLYCOPROTEINS; PEPTIDES;

SYNTHESIS (CHEMICAL);

AMINO ACID; BACTERIAL ENZYME; GAMMA GLUTAMYLTRANSFERASE; GLYCINE; GLYCOPEPTIDE; GLYCOPROTEIN; GLYCOSYLPHOSPHATIDYLINOSITOL; MONOSACCHARIDE; PHOSPHOETHANOLAMINE; SORTASE; SORTASE A; TRISACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENZYME ACTIVITY; ENZYME SUBSTRATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NONHUMAN; PEPTIDE SYNTHESIS; PROTEIN SYNTHESIS; STAPHYLOCOCCUS AUREUS;

AMINO ACID SEQUENCE; AMINOACYLTRANSFERASES; ANTIGENS, CD; ANTIGENS, CD24; ANTIGENS, NEOPLASM; BACTERIAL PROTEINS; CARBOHYDRATE SEQUENCE; CYSTEINE ENDOPEPTIDASES; GLYCOPROTEINS; GLYCOSYLPHOSPHATIDYLINOSITOLS; HUMANS; MOLECULAR SEQUENCE DATA; PEPTIDES; STAPHYLOCOCCUS AUREUS;

EID: 76149104596     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja906611x     Document Type: Article

References (39)

1. Ferguson, M. A. J.; Williams, A. F. Annu. Rev. Biochem. 1988, 57, 285-320.
2. Englund, P. T. Annu. Rev. Biochem. 1993, 62, 121-138.
3. Hwa, K. Adv. Exp. Med. Biol. 2001, 491, 207-214.
4. Robinson, P. J. Cell Biol. Int. Rep. 1991, 15, 761-767.
5. Ferguson, M. A. J. Parasitol. Today 1994, 10, 48-52.
6. Gaulton, G. N.; Pratt, J. C. Semin. Immunol. 1994, 6, 97-104.
7. Kasahara, K.; Sanai, Y. Glycoconjugate J. 2000, 17, 153-162.
8. Loertscher, R.; Lavery, P. Transplant Immunol. 2002, 9, 93-96.
9. Treumann, A.; Lifely, M. R.; Schneider, P.; Ferguson, M. A. J. J. Biol. Chem. 1995, 270, 6088-6099.
10. Schröter, S.; Derr, P.; Conradt, H. S.; Nimtz, M.; Hale, G.; Kirchhoff, C. J. Biol. Chem. 1999, 274, 29862-29873.
11. Kay, R.; Rosten., P. M.; Humphries, R. K. J. Immunol. 1991, 147, 1412-1416.
12. Williams, L. A.; Hock, B. D.; Hart, D. N. J. Blood 1998, 88, 3048-3055.
13. Kadmon, G.; Kowitz, A.; Altevogt, P.; Schachner, M. J. Cell Biol. 1992, 110, 209-218.
14. Rougon, G.; Alterman, L. A.; Dennis, K.; Guo, X. J.; Kinnon, C. Eur. J. Immunol. 1991, 21, 1397-1402.
15. Jackson, D.; Waibel, R.; Weber, E.; Bell, J.; Stahel, R. A. Cancer Res. 1992, 52, 5264-5270.
16. Lim, S.; Oh, S. Pathol. Res. Pract. 2005, 201, 479-486.
17. Tanaka, Y.; Nakahara, Y.; Hojo, H.; Nakahara, Y. Tetrahedron 2003, 59, 4059-4067.
18. Xue, J.; Shao, N.; Guo, Z. J. Org. Chem. 2003, 68, 4020-4029.
19. Shao, N.; Xue, J.; Guo, Z. Angew. Chem., Int. Ed. 2004, 43, 1569-1573.
20. Paulick, M. G.; Wise, A. R.; Forstner, M. B.; Groves, J. T.; Bertozzi, C. R. J. Am. Chem. Soc. 2007, 129, 11543-11550.
21. Becker, C. F. W.; Liu, X.; Olschewski, D.; Castelli, R.; Seidel, R.; Seeberger, P. H. Angew. Chem., Int. Ed. 2008, 47, 8215-8219.
22. Marraffini, L. A.; DeDent, A. C.; Schneewind, O. Microbiol. Mol. Biol. Rev. 2006, 70, 192-221.
23. Huang, X.; Aulabaugh, A.; Ding, W.; Kapoor, B.; Alksne, L.; Tabei, K.; Ellestad, G. Biochemistry 2003, 42, 11307-11315.
24. Ton-That, H.; Mazmanian, S. K.; Alksne, L.; Schneewind, O. J. Biol. Chem. 2002, 277, 7447-7452.
25. Budisa, N. ChemBioChem 2004, 5, 1176-1179.
26. Tsukiji, S.; Nagamune, T. ChemBioChem 2009, 10, 787-798.
27. Mao, H.; Hart, S. A.; Schink, A.; Pollok, B. A. J. Am. Chem. Soc. 2004, 126, 2670-2671.
28. Parthasarathy, R.; Subramanian, S.; Boder, E. T. Bioconjugate Chem. 2007, 18, 469-476.
29. Pritz, S.; Kraetke, O.; Klose, A.; Klose, J.; Rothemund, S.; Fechner, K.; Bienert, M.; Beyermann, M. Angew. Chem., Int. Ed. 2008, 47, 3642-3645.
30. Kobashigawa, Y.; Kumeta, H.; Ogura, K.; Inagaki, F. J. Biomol. NMR 2009, 43, 145-150.
31. Pritz, S.; Wolf, Y.; Kraetke, O.; Klose, J.; Bienert, M.; Beyermann, M. J. Org. Chem. 2007, 72, 3909-3912.
32. Antos, J. M.; Miller, G. M.; Grotenbreg, G. M.; Ploegh, H. L. J. Am. Chem. Soc. 2008, 130, 16338-16343.
33. Samantaray, S.; Marathe, U.; Dasgupta, S.; Nandicoori, V. K.; Roy, R. P. J. Am. Chem. Soc. 2008, 130, 2132-2133.
34. Popp, M. W.; Antos, J. M.; Grotenbreg, G. M.; Spooner, E.; Ploegh, H. L. Nat. Chem. Biol. 2007, 3, 707-708.
35. Tanaka, T.; Yamamoto, T.; Tsukiji, S.; Nagamune, T. ChemBioChem 2008, 9, 802-807.
36. Yamamoto, T.; Nagamune, T. Chem. Commun. 2009, 1022-1023.
37. Ilangumaran, S.; He, H.-T.; Hoessli, D. C. Immunol. Today 2000, 21, 2-7.
38. Trotter, J.; Klein, C.; Kramer, E. Neuroscientist 2000, 6, 271-284.
39. Guo, X.; Wang, Q.; Swarts, B. M.; Guo, Z. J. Am. Chem. Soc. 2009, 131, 9878-9879.