Detailed Dissection of a New Mechanism for Glycoside Cleavage: α-1,4-Glucan Lyase

Biochemistry

Volumn 42, Issue 44, 2003, Pages 13081-13090

  Lee, Seung Seo ^a   Yu, Shukun ^b   Withers, Stephen G ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b DANISCO A S   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DEUTERIUM; FLUORINE; PH EFFECTS; SUBSTITUTION REACTIONS;

ENZYME MECHANISM;

ENZYMES;

1 DEOXYNOJIRIMYCIN; 5 FLUORO ALPHA DEXTRO GLUCOPYRANOSYL FLUORIDE; ACARBOSE; ALPHA 1,4 GLUCAN LYASE; DEUTERIUM; FLUORIDE; FLUORINE; GLYCOSIDE; LYASE; UNCLASSIFIED DRUG;

ALGA; AMINO ACID SEQUENCE; ARTICLE; ELIMINATION REACTION; ENZYME ANALYSIS; ENZYME DEGRADATION; ENZYME MECHANISM; GLYCOSYLATION; GRACILARIOPSIS; INHIBITION KINETICS; MOLECULAR MECHANICS; NONHUMAN; NUCLEOTIDE SEQUENCE; PH; PHASE TRANSITION; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION ANALYSIS;

1-DEOXYNOJIRIMYCIN; ACARBOSE; ANIMALS; CATALYSIS; DEUTERIUM; ENZYME ACTIVATION; ENZYME INHIBITORS; GLUCANS; GLUCONATES; GLUCOSE; GLYCOSIDES; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; IMINES; KINETICS; MICE; POLYSACCHARIDE-LYASES; SUBSTRATE SPECIFICITY;

ALGAE; FELIS CATUS; GRACILARIOPSIS;

EID: 0242675935     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi035189g     Document Type: Article

References (59)

1. Sinnott, M. L. (1990) Chem. Rev. 90, 1171-1202.
2. McCarter, J. D., and Withers, S. G. (1994) Curr. Opin. Struct. Biol. 4, 885-892.
3. Zechel, D. L., and Withers, S. G. (2000) Acc. Chem. Res. 33, 11-18.
4. Henrissat, B. (1991) Biochem. J. 280, 309-316.
5. Henrissat, B., and Bairoch, A. (1993) Biochem. J. 293, 781-788.
6. Henrissat, B., and Davies, G. J. (2000) Plant Physiol. 124, 1515-1519.
7. Ernst, S., Langer, R., Cooney, C. L., and Sasisekharan, R. (1995) Crit. Rev. Biochem. Mol. Biol. 30, 387-444.
8. Rye, C. S., and Withers, S. G. (2002) J. Am. Chem. Soc. 124, 9756-9767.
9. Yu, S., Bojsen, K., Svensson, B., and Marcussen, J. (1999) Biochim. Biophys. Acta 1433, 1-15.
10. Yu, S., Kenne, L., and Pedersén, M. (1993) Biochim. Biophys. Acta 1156, 313-320.
11. Yu, S., and Pedersén, M. (1993) Planta 191, 137-142.
12. Yu, S., Ahmad, T., Kenne, L., and Pedersén, M. (1995) Biochim. Biophys. Acta 1244, 1-9.
13. Yu, S., Christensen, T. M. I. E., Kragh, K. M., Bojsen, K., and Marcussen, J. (1997) Biochim. Biophys. Acta 1339, 311-320.
14. Kametani, S., Shiga, Y., and Akanuma, H. (1996) Eur. J. Biochem. 242, 832-838.
15. Shiga, Y., Kametani, S., Kadokura, T., and Akanuma, H. (1999) J. Biochem. 125, 166-172.
16. Bojsen, K., Yu, S., Kragh, K. M., and Marcussen, J. (1999) Biochim. Biophys. Acta 1430, 396-402.
17. Bojsen, K., Yu, S., and Marcussen, J. (1999) Plant Mol. Biol. 40, 445-454.
18. Legler, G. (1990) Adv. Carbohydr. Chem. Biochem. 48, 319-384.
19. Yoshinaga, K., Fujisue, M., Abe, J., Hanashiro, I., Takeda, Y., Muroya, K., and Hizukuri, S. (1999) Biochim. Biophys. Acta 1472, 447-454.
20. Nyvall, P., Pedersén, M., Kenne, L., and Gacesa, P. (2000) Phytochemistry 54, 139-145.
21. Quaroni, A., and Semenza, G. (1976) J. Biol. Chem. 251, 3250-3253.
22. Hermans, M. M. P., Kroos, M. A., van Beeumen, J., Oostra, B. A., and Reuser, A. J. J. (1991) J. Biol. Chem. 266, 13507-3512.
23. Iwanami, S., Matsui, H., Kimura, A., Ito, H., Mori, H., Honma, M., and Chiba, S. (1995) Biosci. Biotech. Biochem. 59, 459-463.
24. Kimura, A., Takaya M., Fukushi Y., Mori, H., Matsui, H., and Chiba, S. (1997) Biosci. Biotech. Biochem. 61, 1091-1098.
25. Lee, S. S., He, S., and Withers, S. G. (2001) Biochem. J. 359, 381-386.
26. Lee, S. S., Yu, S., and Withers, S. G. (2002) J. Am. Chem. Soc. 124, 4948-4949.
27. Cogoli, A., and Semenza, G. (1975) J. Biol. Chem. 250, 7802-7809.
28. Igaki, S., and Chiba, S. (1989) Abstracts of the Annual Meeting of the Japan Agricultural Society, Niigata, Japan, 3Hp16, p 292, Agricultural Chemical Society of Japan, Tokyo.
29. Konstantinidis, A., and Sinnott, M. L. (1991) Biochem. J. 279, 587-593.
30. Praly, J.-P., and Descotes, G. (1987) Tetrahedron Lett. 28, 1405-1408.
31. Adamson, J., Foster, A. B., Hall, L. D., Johnson, R. N., and Hesse, R. M. (1970) Carbohydr. Res. 15, 351-359.
32. McCarter, J. D., and Withers, S. G. (1996) J. Am. Chem. Soc. 118, 241-242.
33. Hayashi, M., Hashimoto, S., and Noyori, R. (1984) Chem. Lett. 1747-1750.
34. Wolfrom, M. L., and Thompson, A. (1963) Methods Carbohydr. Chem. 2, 211-215.
35. Kooners, H. J., de Kok, A. J., Romers, C., and van Boom, J. H. (1980) Recl. Trav. Chim. Pays-Bas 99, 355-362.
36. Yamaguchi, M., Horiguchi, A., Fukuda, A., and Minami, T. (1990) J. Chem. Soc., Perkin Trans. 1, 1079-1082.
37. Apparu, M., Blanc-Muesser, M., Defaye, J., and Driguez, H. (1981) Can. J. Chem. 59, 314-320.
38. Farkas, I., Szabo, I. F., and Bognar, R. (1976) Carbohydr. Res. 48, 136-138.
39. Joshi, M. D., Sidhu, G., Pot, I., Brayer, G. D., Withers, S. G., and McIntosh, L. P. (2000) J. Mol. Biol. 299, 255-279.
40. McCarter, J. D., and Withers, S. G. (1996) J. Biol. Chem. 271, 6889-6894.
41. Kimura, A., Somoto, A., Mori, H., Sakai, O., Matsui, H., and Chiba, S. (1997) Biosci. Biotech. Biochem. 61, 475-479.
42. Kempton, J. B., and Withers, S. G. (1992) Biochemistry 31, 9961-9969.
43. Vocadlo, D. J., Wicki, J., Rupitz, K., and Withers, S. G. (2002) Biochemistry 41, 9727-9735.
44. Tull, D., and Withers, S. G. (1994) Biochemistry 33, 6363-6370.
45. Mosi, R., Sham, H., Uitdehaag, J. C. M., Ruiterkamp, R., Dijkstra, B. W., and Withers, S. G. (1998) Biochemistry 37, 17192-17198.
46. Hoos, R., Vasella, A., Rupitz, K., and Withers, S. G. (1997) Carbohydr. Res. 298, 291-298.
47. Heightman, T. D., and Vasella, A. T. (1999) Angew. Chem., Int. Ed. Engl. 38, 750-770.
48. Williams, S. J., Hoos, R., and Withers, S. G. (2000) J. Am. Chem. Soc. 122, 2223-2235.
49. Fry, A. (1972) Chem. Soc. Rev. 1, 163-210.
50. Cram, D. J., and Tadanier, J. (1959) J. Am. Chem. Soc. 81, 2737-2748.
51. More O'Ferrall, R. A. (1970) J. Chem. Soc. B, 274-277.
52. Bunnet, J. F., Davis, G. T., and Tanida, H. (1962) J. Am. Chem. Soc. 84, 1606-1614.
53. Morgan, P. M., Sala, R. F., and Tanner, M. E. (1997) J. Am. Chem. Soc. 119, 10269-10277.
54. Withers, S. G., MacLennan, D. J., and Street, I. P. (1986) Carbohydr. Res. 154, 127-144.
55. Blint, R. J., McMahon, T. B., and Beauchamp, J. L. (1974) J. Am. Chem. Soc. 96, 1269-1278.
56. Sinnott, M. L., and Jencks, W. P. (1980) J. Am. Chem. Soc. 102, 2026-2032.
57. Banait, N. S., and Jencks, W. P. (1991) J. Am. Chem. Soc. 113, 7958-7963.
58. Uitdehaag, J. C. M., Mosi, R., Kalk, K. H., van der Veen, B. A., Dijkhuizen, L., Withers, S. G., and Dijkstra, B. W. (1999) Nat. Struct. Biol. 6, 432-436.
59. Smar, M., Short, S. A., and Wolfenden, R. (1991) Biochemistry 30, 7908-7912.