Synthesis of galactose-containing oligosaccharides through superbeads and superbug approaches: Substrate recognition along different biosynthetic pathways

Methods in Enzymology

Volumn 362, Issue , 2003, Pages 106-124

  Zhang, Jianbo ^b   Chen, Xi ^a   Shao, Jun ^b   Liu, Ziye ^b   Kowal, Przemyslaw ^b   Lu, Yuquan ^b   Wang, Peng G ^b  

^a Neose Technologies Inc   (United States)

^b WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPITOPE; GALACTOSE; GALACTOSIDE; OLIGOSACCHARIDE; TRITIUM; URIDINE DIPHOSPHATE GALACTOSE;

ARTICLE; BIOSYNTHESIS; ESCHERICHIA COLI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; NEISSERIA GONORRHOEAE; NONHUMAN; PLASMID; PRIORITY JOURNAL; SYNTHESIS;

ESCHERICHIA COLI; NEISSERIA; NEISSERIA GONORRHOEAE;

EID: 0043029648     PISSN: 00766879     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0076-6879(03)01009-7     Document Type: Article

References (65)

1. (a) A. Kobata, Acc. Chem. Res. 26, 319 (1993);
2. (b) C.-H. Wong, R. L. Halcomb, Y. Ichikawa, and T. Kajimoto, Angew. Chem. Int. Ed. Engl. 34, 412 (1995);
3. (c) R. A. Dwek, Chem. Rev. 96, 683 (1996);
4. (d) A. Varki, R. D. Cummings, J. Esko, H. Freeze, and G. Hart (Eds.), "Essentials of Glycobiology." Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, 1999.
5. (a) D. K. C. Cooper, Clin. Trans. 6, 178 (1992);
6. (b) D. K. C. Cooper, A. H. Good, E. Koren, R. Oriol, A. J. Malcolm, R. M. Ippolito, F. A. Neethling, Y. Ye, E. Romano, and N. Zuhdi, Transplant. Immunol. 1, 198 (1993);
7. (c) U. Galili, Sci. Med. 5, 28 (1998).
8. (a) U. Galili, Blood Cells 14, 205 (1988);
9. (b) U. Galili, Immunol. Ser. 55, 355 (1992);
10. (c) U. Galili, Immunol. Today 14, 480 (1993);
11. (d) U. Galili, Springer Semin. Immunopathol. 15, 155 (1993);
12. (e) D. K. C. Cooper, E. Koren, and R. Oriol, Immunol. Rev. 141, 31 (1994);
13. (f) M. S. Sandrin, H. A. Vaughan and I. F. C. McKenzie, Transplant. Rev. 8, 134 (1994);
14. (g) B. E. Samuelsson, L. Rydberg, M. E. Breimer, A. Backer, M. Gustavsson, J. Holgersson, E. Karlsson, A.-E. Uyterwaal, T. Cairns, and K. Welsh, Immunol. Rev. 141, 151 (1994);
15. (h) R. Hamadeh, U. Galili, P. Zhou, and J. Griffiss, Clin. Diagn. Lab. Immunol. 2, 125 (1995);
16. (i) X. Chen, P. R. Andreana, and P. G. Wang, Curr. Opin. Chem. Biol. 3, 650 (1999).
17. U. Galili, Biochimie 83, 557 (2001).
18. (a) C. A. Lingwood, Biochim. Biophys. Acta 1455, 375 (1999);
19. (b) J. C. Paton and A. W. Paton, Clin. Microbiol. Rev. 11, 450 (1998);
20. (c) M. A. Karmali, M. Petric, C. Lim, P. C. Fleming, G. S. Arbus, and H. Lior, J. Infect. Dis. 151, 775 (1985).
21. (a) M. P. Jackson, Microb. Pathog. 8, 235 (1990);
22. (b) J. P. Nataro, and J. B. Kaper, Clin. Microbiol. Rev. 11, 142 (1998);
23. (c) J. C. Paton and A. W. Paton, Clin. Microbiol. Rev. 11, 450 (1998).
24. (a) R. J. P. M. Scholten, B. Kuipers, H. A. Valkenburg, J. Kankert, W. D. Zollinger, and J. T. Poolman, J. Med. Microbiol. 41, 236 (1994);
25. (b) J. Kihlberg and G. Magnusson, Pure Appl. Chem. 68, 2119 (1996).
26. K. Nishikawa, K. Matsuoka, E. Kita, N. Okabe, M. Mizuguchi, K. Kino, S. Miyazawa, C. Yamasaki, J. Aoki, S. Takashima, Y. Yamakawa, M. Nishijima, D. Terunuma, H. Kuzuhara, and Y. Natori, Proc. Natl. Acad. Sci. USA 99, 7669 (2002).
27. (a) J. J. Donnelly and R. Rappulo, Nat. Med. 6, 257 (2000);
28. (b) G. Mulvey, P. I. Kitov, P. Marcato, D. R. Bundle, and G. D. Armstrong, Biochimie 83, 841 (2001).
29. P. Sears and C.-H. Wong, Angew. Chem. Int. Ed. Engl. 38, 2300 (1999).
30. (a) K. Koike, M. Sugimoto, S. Sato, Y. Ito, Y. Nakahara, T. Ogawa, Carbohydr. Res. 163, 189-208 (1987);
31. (b) K. C. Nicolaou, T. Caufield, H. Kataoka, T. Kumazawa, J. Am. Chem. Soc. 110, 7910-7912 (1998);
32. (c) D. Qui, R. R. Schmidt, Liebigs Ann. 217-224 (1992);
33. (d) W. Zhang, J.-Q. Wang, J. Li, L.-B. Yu, P. G. Wang, J. Carb. Chem. 18, 1009-1017; 1999.
34. (a) M. M. Palcic, Curr. Opin. Biotechnol. 10, 616 (1999);
35. (b) P. Sears and C.-H. Wong, Science 291, 2344 (2001);
36. (c) X. Chen, P. Kowal, and P. G. Wang, Curr. Opin Drug Discov. Dev. 3, 756 (2000);
37. (d) J. Zhang, B. Wu, Z. Liu, P. Kowal, X. Chen, J. Shao, and P. G. Wang, Curr. Org. Chem. 5, 1169 (2001).
38. (a) C.-H. Wong, S. L. Haynie, and G. M. Whitesides, J. Org. Chem. 47, 5418 (1982);
39. (b) M. Gilbert, R. Bayer, A.-M. Cunningham, S. DeFrees, Y. Gao, D. C. Watson, N. M. Young, and W. W. Wakarchuk, Nat. Biotechnol. 16, 769 (1998).
40. (a) J. Fang, J. Li, X. Chen, Y. Zhang, J. Wang, Z. Guo, K. Brew, and P. G. Wang, J. Am. Chem. Soc. 120, 6635 (1998);
41. (b) J. Zhang, P. Kowal, J. Fang, P. Andreana, and P. G. Wang, Carbohydr. Res. 337, 969 (2002).
42. (a) X. Chen, J. Fang, J. Zhang, Z. Liu, J. Shao, P. Kowal, P. Andreana, and P. G. Wang, J. Am. Chem. Soc. 123, 2081 (2001);
43. (b) X. Chen, J. Zhang, P. Kowal, Z. Liu, P. R. Andreana, Y. Lu, and P. G. Wang, J. Am Chem. Soc. 123, 8866 (2001);
44. (c) X. Chen, Z. Liu, J. Zhang, W. Zheng, P. Kowal, and P. G. Wang, ChemBioChem 3, 47 (2002).
45. (a) N. L. S. Clair and M. A. Navia, J. Am. Chem. Soc. 114, 7314 (1992);
46. (b) J. Thiem and T. Wiemann, Synthesis-Stuttgart 141 (1992);
47. (c) L. Bulow and K. Mosbach, Trends Biotechnol. 9, 226 (1991);
48. (d) L. Bulow, Eur. J. Biochem. 163, 443 (1987);
49. (e) C. Suge and C. Merienne, Carbohydr. Res. 151, 147 (1986).
50. Z. Liu, J. Zhang, X. Chen, and P. G. Wang, ChemBioChem 3, 348 (2002).
51. (a) C. H. Hokke, A. Zervosen, L. Elling, D. H. Joziasse, and D. H. van Den Eihnden, Glycoconj. J. 13, 687 (1996);
52. (b) J. W. Fang, X. Chen, W. Zhang, A. Janczuk, and P. G. Wang, Carbohydr. Res. 329, 873 (2000);
53. (c) X. Chen, W. Zhang, J.-Q. Wang, J. W. Fang, and P. G. Wang, Biotech. Prog. 16, 595 (2000);
54. (d) K. Sujino, T. Uchiyama, O. Hindsgaul, N. O. L. Seto, W. Wakarchuk, and M. M. Palcic, J. Am. Chem. Soc. 122, 1261 (2000).
55. (a) S. Koizumi, T. Endo, K. Tabata, and A. Ozaki, Nat. Biotechnol. 16, 847 (1998);
56. (b) T. Endo, S. Koizumi, K. Tabata, S. Kakita, and A. Ozaki, Carbohydr. Res. 316, 179 (1999);
57. (c) K. Tabata, S. Koizumi, T. Endo, and A. Ozaki, Biotech. Lett. 22, 479 (2000);
58. (d) T. Endo, S. Koizumi, K. Tabata, and A. Ozaki, Appl. Microbiol. Biotechnol. 53, 257 (2000);
59. (e) T. Endo, S. Koizumi, K. Tabata, S. Kakita, and A. Ozaki, Carbohydr. Res. 330, 439 (2001).
60. (a) R. Patnaik and J. Liao, Appl. Environ. Microbiol. 60, 3903 (1994);
61. (b) J. T. Kealey, L. Liu, D. V. Santi, M. C. Betlack, and P. J. Barr, Proc. Natl. Acad. Sci. USA 95, 505 (1998);
62. (c) K. Li and J. W. Frost, J. Am. Chem. Soc. 120, 10545 (1998).
63. (d) W. W. Wakarchuk, A. Cunningham, D. C. Watson, and N. M. Young, Protein Eng. 11, 295 (1998).
64. (a) W. Zhang, J. Wang, J. Li, L. Yu, and P. G. Wang, J. Carbohydr. Chem. 18, 1009 (1999);
65. (b) J. Fang, Ph.D. thesis. Wayne State University, Detroit, MI, 2000.