Conversion of inverting glycoside hydrolases into catalysts for synthesizing glycosides employing a glycosynthase strategy

Trends in Glycoscience and Glycotechnology

Volumn 21, Issue 117, 2009, Pages 23-39

  Motomitsu, Kitaoka ^a   Yuji, Honda ^a,b   Shinya, Fushinobu ^c   Masafumi, Hidaka ^a,c   Takane, Katayama ^b   Kenji, Yamamoto ^d  

^a NATIONAL FOOD RESEARCH INSTITUTE   (Japan)

^b ISHIKAWA PREFECTURAL UNIVERSITY   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

^d KYOTO UNIVERSITY   (Japan)

Author keywords

fucosidase; Glycosylfluoride; Glycosynthase; Hehre resynthesis hydrlysis mechanism; Inverting hydrolase; Reducing end xylose releasing exo oligoxylanase

Indexed keywords

EID: 65949085808     PISSN: 09157352     EISSN: None     Source Type: Journal    
DOI: 10.4052/tigg.21.23     Document Type: Review

References (83)

1. Nishimoto, M., and Kitaoka, M. (2007) Biosci. Biotechnol. Biochem. 71, 2101-2104
2. Totani, K., Yasutake, N., Murata, T., and Usui, T. (2004) Trends Glycosci. Glycotechnol. 16, 383-392
3. Liu, Z., Lu, Y., Zhang, J., Pardee, K., and Wang, P. G. (2003) Appl. Environ. Microbiol. 69, 2110-2115
4. Koizumi, S. (2003) Trends Glycosci. Glycotechnol. 15, 65-74
5. Kitaoka, M., and Hayashi, K. (2002) Trends Glycosci. Glycotechnol. 14, 35-50
6. Murata, T., and Usui, T. (2000) Trends Glycosci. Glycotechnol. 12, 161-174
7. Henrissat, B., and Bairoch, A. (1996) Biochem. J. 316, 695-696
8. Davies, G., and Henrissat, B. (1995) Structure 3, 853-859
9. Henrissat, B., and Bairoch, A. (1993) Biochem. J. 293, 781-788
10. Henrissat, B. (1991) Biochem. J. 280, 309-316
11. Sinnott, M. L. (1990) Chem. Rev. 90, 1171-1202
12. Nakakuki, T. (2003) Trends Glycosci. and Glycotechnol. 15, 57-64
13. Hehre, E. J., Brewer, C. F., and Genghof, D. S. (1979) J. Biol. Chem. 254, 5942-5950
14. Becker, D., Johnson, K. S., Koivula, A., Schulein, M., and Sinnott, M. L. (2000) Biochem. J. 345, 315-319
15. Williams, S. J., and Withers, S. G. (2000) Carbohydr. Res. 327, 27-46
16. Matsui, H., Blanchard, J. S., Brewer, C. F., and Hehre, E. J. (1989) J. Biol. Chem. 264, 8714-8716
17. Nakano, M., Brewer, C. F., Kasumi, T., and Hehre, E. J. (1989) Carbohydr. Res. 194, 139-144
18. Kasumi, T., Tsumuraya, Y., Brewer, C. F., Kersters-Hilderson, H., Claeyssens, M., and Hehre, E. J. (1987) Biochemistry 26, 3010-3016
19. Kasumi, T., Brewer, C. F., Reese, E. T., and Hehre, E. J. (1986) Carbohydr. Res. 146, 39-49
20. Hehre, E. J., Sawai, T., Brewer, C. F., Nakano, M., and Kanda, T. (1982) Biochemistry 21, 3090-3097
21. Konstantinidis, A. K., Marsden, I., and Sinnott, M. L. (1993) Biochem. J. 291, 883-888
22. Kitahata, S., Brewer, C. F., Genghof, D. S., Sawai, T., and Hehre, E. J. (1981) J. Biol. Chem. 256, 6017-6026
23. Jakeman, D. L., and Withers, S. G. (2002) Trends Glycosci. Glycotechnol. 14, 13-25
24. MacKenzie, L. F., Wang, Q. P., Warren, R. A. J., and Withers, S. G. (1998) J. Am. Chem. Soc. 120, 5583-5584
25. Tao, H., Peralta-Yahya, P., Decatur, J., and Cornish, V. W. (2008) Chembiochem 9, 681-684
26. Wilkinson, S. M., Liew, C. W., Mackay, J. P., Salleh, H. M., Withers, S. G., and McLeod, M. D. (2008) Org. Lett. 10, 1585-1588
27. Wang, L. X. (2008) Carbohydr. Res. 343, 1509-1522
28. Shaikh, F. A., and Withers, S. G. (2008) Biochem. Cell Biol. 86, 169-177
29. Ben-David, A., Shoham, G., and Shoham, Y. (2008) Chem. Biol. 15, 546-551
30. Marton, Z., Tran, V., Tellier, C., Dion, M., Drone, J., and Rabiller, C. (2008) Carbohydr. Res. 343, 2939-2946
31. Faijes, M., and Planas, A. (2007) Carbohydr. Res. 342, 1581-1594
32. Blanchard, S., Armand, S., Couthino, P., Patkar, S., Vind, J., Samain, E., Driguez, H., and Cottaz, S. (2007) Carbohyd.r Res. 342, 710-716
33. Yang, M., Davies, G. J., and Davis, B. G. (2007) Angew. Chem. Int. Ed. Engl. 46, 3885-3888
34. Hommalai, G., Withers, S. G., Chuenchor, W., Cairns, J. R., and Svasti, J. (2007) Glycobiology 17, 744-753
35. Ben-David, A., Bravman, T., Balazs, Y. S., Czjzek, M., Schomburg, D., Shoham, G., and Shoham, Y. (2007) Chembiochem 8, 2145-2151
36. Piens, K., Henriksson, A. M., Gullfot, F., Lopez, M., Faure, R., Ibatullin, F. M., Teeri, T. T., Driguez, H., and Brumer, H. (2007) Org. Biomol. Chem. 5, 3971-3978
37. Mullegger, J., Chen, H. M., Warren, R. A., and Withers, S. G. (2006) Angew. Chem. Int. Ed. Engl. 45, 2585-2588
38. Vaughan, M. D., Johnson, K., DeFrees, S., Tang, X., Warren, R. A., and Withers, S. G. (2006) J. Am. Chem. Soc. 128, 6300-6301
39. Kim, Y. W., Fox, D. T., Hekmat, O., Kantner, T., McIntosh, L. P., Warren, R. A., and Withers, S. G. (2006) Org. Biomol. Chem. 4, 2025-2032
40. Faijes, M., Saura-Valls, M., Perez, X., Conti, M., and Planas, A. (2006) Carbohydr. Res. 341, 2055-2065
41. Sugimura, M., Nishimoto, M., and Kitaoka, M. (2006) Biosci. Biotechnol. Biochem. 70, 1210-1217
42. Faure, R., Saura-Valls, M., Brumer, H., 3rd, Planas, A., Cottaz, S., and Driguez, H. (2006) J. Org. Chem. 71, 5151-5161
43. Tao, H., Peralta-Yahya, P., Lin, H., and Cornish, V. W. (2006) Bioorg. Med. Chem. 14, 6940-6953
44. Hancock, S. M., Vaughan, M. D., and Withers, S. G. (2006) Curr. Opin. Chem. Biol. 10, 509-519
45. Drone, J., Feng, H.-y., Tellier, C., Hoffmann, L., Tran, V., Rabiller, C., and Dion, M. (2005) Eur. J. Org. Chem. 2005, 1997-1983
46. Trincone, A., Giordano, A., Perugino, G., Rossi, M., and Moracci, M. (2005) Chembiochem 6, 1431-1437
47. Kim, Y. W., Chen, H., and Withers, S. G. (2005) Carbohydr. Res. 340, 2735-2741
48. Daines, A. M., Maltman, B. A., and Flitsch, S. L. (2004) Curr. Opin. Chem. Biol. 8, 106-113
49. Watts, A. G., and Withers, S. G. (2004) Biochem. J. 380, e9-10
50. Kim, Y. W., Lee, S. S., Warren, R. A., and Withers, S. G. (2004) J. Biol. Chem. 279, 42787-42793
51. Lin, H., Tao, H., and Cornish, V. W. (2004) J. Am. Chem. Soc. 126, 15051-15059
52. van Lieshout, J., Faijes, M., Nieto, J., van der Oost, J., and Planas, A. (2004) Archaea 1, 285-292
53. Fairweather, J. K., Hrmova, M., Rutten, S. J., Fincher, G. B., and Driguez, H. (2003) Chemistry 9, 2603-2610
54. Jahn, M., Stoll, D., Warren, R. A., Szabo, L., Singh, P., Gilbert, H. J., Ducros, V. M., Davies, G. J., and Withers, S. G. (2003) Chem Commun (Camb), 1327-1329
55. Ducros, V. M., Tarling, C. A., Zechel, D. L., Brzozowski, A. M., Frandsen, T. P., von Ossowski, I., Schulein, M., Withers, S. G., and Davies, G. J. (2003) Chem. Biol. 10, 619-628
56. Trincone, A., Giordano, A., Perugino, G., Rossi, M., and Moracci, M. (2003) Bioorg. Med. Chem. Lett. 13, 4039-4042
57. Faijes, M., Perez, X., Perez, O., and Planas, A. (2003) Biochemistry 42, 13304-13318
58. Jakeman, D. L., and Withers, S. G. (2002) Can. J. Chem. 80, 866-870
59. Hrmova, M., Imai, T., Rutten, S. J., Fairweather, J. K., Pelosi, L., Bulone, V., Driguez, H., and Fincher, G. B. (2002) J. Biol. Chem. 277, 30102-30111
60. Okuyama, M., Mori, H., Watanabe, K., Kimura, A., and Chiba, S. (2002) Biosci. Biotechnol. Biochem. 66, 928-933
61. Tolborg, J. F., Petersen, L., Jensen, K. J., Mayer, C., Jakeman, D. L., Warren, R. A., and Withers, S. G. (2002) J. Org. Chem. 67, 4143-4149
62. Fairweather, J. K., Faijes, M., Driguez, H., and Planas, A. (2002) Chembiochem 3, 866-873
63. Nashiru, O., Zechel, D. L., Stoll, D., Mohammadzadeh, T., Warren, R. A., and Withers, S. G. (2001) Angew. Chem. Int. Ed. Engl. 40, 417-420
64. Mayer, C., Jakeman, D. L., Man, M., Karjala, G., Gal, L., Warren, R. A., and Withers, S. G. (2001) Chem. Biol. 8, 437-443
65. Brun, E., Brumer, H., 3rd, MacKenzie, L. F., Withers, S. G., and Mclntosh, L. P. (2001) J. Biomol. NMR 21, 67-68
66. Mayer, C., Zechel, D. L., Reid, S. P., Warren, R. A., and Withers, S. G. (2000) FEBS Lett. 466, 40-44
67. Trincone, A., Perugino, G., Rossi, M., and Moracci, M. (2000) Bioorg. Med. Chem. Lett. 10, 365-368
68. Malet, C., and Planas, A. (1998) FEBS Lett. 440, 208-212
69. Fushinobu, S., Hidaka, M., Honda, Y., Wakagi, T., Shoun, H., and Kitaoka, M. (2005) J. Biol. Chem. 280, 17180-17186
70. Honda, Y., Fushinobu, S., Hidaka, M., Wakagi, T., Shoun, H., and Kitaoka, M. (2005) Acta Crystallogr. Sect. F Struct. Biol. Cryst. Commun. 61, 291-292
71. Honda, Y., and Kitaoka, M. (2004) J. Biol. Chem. 279, 55097-55103
72. Collins, T., Meuwis, M. A., Stals, I., Claeyssens, M., Feller, G., and Gerday, C. (2002) J. Biol. Chem. 277, 35133-35139
73. Van Petegem, F., Collins, T., Meuwis, M. A., Gerday, C., Feller, G., and Van Beeumen, J. (2003) J Biol Chem 278, 7531-7539
74. Guerin, D. M., Lascombe, M. B., Costabel, M., Souchon, H., Lamzin, V., Beguin, P., and Alzari, P. M. (2002) J. Mol. Biol. 316, 1061-1069
75. Takami, H., Nakasone, K., Takaki, Y., Maeno, G., Sasaki, R., Masui, N., Fuji, F., Hirama, C., Nakamura, Y., Ogasawara, N., Kuhara, S., and Horikoshi, K. (2000) Nucleic Acids Res. 28, 4317-4331
76. Shintate, K., Kitaoka, M., Kim, Y. K., and Hayashi, K. (2003) Carbohydr. Res. 338, 1981-1990
77. Honda, Y., and Kitaoka, M. (2006) J. Biol. Chem. 281, 1426-1431
78. Honda, Y., Fushinobu, S., Hidaka, M., Wakagi, T., Shoun, H., Taniguchi, H., and Kitaoka, M. (2008) Glycobiology 18, 325-330
79. Collins, T., De Vos, D., Hoyoux, A., Sawides, S. N., Gerday, C., Van Beeumen, J., and Feller, G. (2005) J. Mol. Biol. 354, 425-435
80. Wada, J., Honda, Y., Nagae, M., Kato, R., Wakatsuki, S., Katayama, T., Taniguchi, H., Kumagai, H., Kitaoka, M., and Yamamoto, K. (2008) FEBS Lett. 582, 3739-3743
81. Katayama, T., Sakuma, A., Kimura, T., Makimura, Y., Hiratake, J., Sakata, K., Yamanoi, T., Kumagai, H., and Yamamoto, K. (2004) J. Bacteriol. 186, 4885-4893
82. Katayama, T., Fujita, K., and Yamamoto, K. (2005) J. Biosci. Bioeng. 99, 457-465
83. Nagae, M., Tsuchiya, A., Katayama, T., Yamamoto, K., Wakatsuki, S., and Kato, R. (2007) J. Biol. Chem. 282, 18497-18509