The role of sugar substituents in glycoside hydrolysis

Journal of the American Chemical Society

Volumn 122, Issue 7, 2000, Pages 1270-1277

  Namchuk, Mark N ^a   McCarter, John D ^a   Becalski, Adam ^a   Andrews, Trevor ^a   Withers, Stephen G ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOPYRANOSIDE; GLYCOSIDE;

ARTICLE; CHEMICAL STRUCTURE; HYDROLYSIS; REACTION ANALYSIS; SOLVATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033996047     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992044h     Document Type: Article

References (59)

1. Amyes, T. L.; Jencks, W. P. J. Am. Chem. Soc. 1989, 111, 7900-7909.
2. Banait, N. S.; Jencks, W. P. J. Am. Chem. Soc. 1991, 113, 7951-7958.
3. Bennet, A.; Sinnott, M. L. J. Am. Chem. Soc. 1986, 108, 7287-7294.
4. Capon, B. Chem. Rev. 1969, 69, 407-498.
5. Huang, X.; Surry, C.; Hiebert, T.; Bennet, A. J. J. Am. Chem. Soc. 1995, 117, 10614-10621.
6. Sinnott, M. L.; Jencks, W. P. J. Am. Chem. Soc. 1980, 102, 2026-2032.
7. Zhu, J.; Bennet, A. J. J. Am. Chem. Soc. 1998, 120, 3887-3893.
8. Cocker, D.; Sinnott, M. L. J. Chem. Soc., Perkin Trans. 2 1975, 1391-1393.
9. Horenstein, B. A.; Bruner, M. J. Am. Chem. Soc. 1996, 118, 10371-10379.
10. Knier, B. L.; Jencks, W. P. J. Am. Chem. Soc. 1980, 102, 6789-6798.
11. Young, P. R.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 8238-8247.
12. Buckley, N.; Oppenheimer, N. J. J. Org. Chem. 1996, 61, 8039-8047.
13. Buckley, N.; Oppenheimer, N. J. J. Org. Chem. 1996, 61, 8048-8062.
14. Edward, J. T. Chem. Ind. (London) 1955, 1102-1104.
15. 31,55-58 and that the inductive component is relatively minor.
16. Franks, F.; Ravenhill, J. R.; Reid, D. S. J. Solution Chem. 1972, 1, 3-9.
17. Mega, T.; Matsushima, Y. J. Biochem. 1983, 94, 1637-1647.
18. Overend, W. G.; Rees, C. W.; Sequeria, J. S. J. Am. Chem. Soc. 1962, 84, 3429-3440.
19. Withers, S. G.; Percival, M. D.; Street, I. P. Carbohydr. Res. 1989, 187, 43-66.
20. Withers, S. G.; MacLennan, D. J.; Street, I. P. Carbohydr. Res. 1986, 154, 127-144.
21. Hengge, A. C. J. Am. Chem. Soc. 1992, 114, 2747-2748.
22. Horton, D.; Luetzow, A. E. J. Chem. Soc. Chem. Commun. 1971, 79-81.
23. Some compounds are referred to by trivial designations for clarity, e.g., 3dDNPglc for 2,4-dinitrophenyl 3-deoxy glucopyranoside rather than 2,4-dinitrophenyl 3-deoxy-D-xylo-hexopyranoside. Note that 2dDNPglc, 3dDNPglc, and 4dDNPglc may with equal justification be referred to, respectively, as 2dDNPman, 3dDNPall, and 4dDNPgal.
24. Linert, W.; Jameson, R. F. Chem. Soc. Rev. 1989, 18, 477-505.
25. Handlon, A. L.; Oppenheimer, N. J. J. Org. Chem. 1991, 56, 5009-5010.
26. Timell, T. E.; Enterman, W.; Spencer, F.; Soltes, E. J. Can. J. Chem. 1965, 43, 2296-2305.
27. Andrews, C. W.; Fraser-Reid, B.; Bowen, J. P. J. Am. Chem. Soc. 1991, 113, 8293-8298.
28. Kajimoto, T.; Liu, K. K. C.; Pederson, R. L.; Zhong, Z.; Ichikawa, Y.; Porco, J. A., Jr.; Wong, C. H. J. Am. Chem. Soc. 1991, 113, 6187-6196.
29. Winkler, D. A.; Holan, G. J. Med. Chem. 1989, 32, 2084-2089.
30. Westheimer, F. H.; Kirkwood, J. G. J. Chem. Phys. 1938, 6, 513-517.
31. Baker, F. W.; Parish, R. C.; Stock, L. M. J. Am. Chem. Soc. 1967, 89, 5677-5685.
32. 1.
33. 1.
34. Abraham, R. J.; Chambers, E. C.; Thomas, W. A. Carbohydr. Res. 1992, 226, C1.
35. Woods, R. J.; Andrews, C. W.; Bowen, J. P. J. Am. Chem. Soc. 1992, 114, 859-864.
36. Miljkovic, M.; Yeagley, D.; Deslongchamps, P.; Dory, Y. L. J. Org. Chem. 1997, 62, 7597-7604.
37. Stewart, R. The Proton, Applications to Organic Chemistry: Academic Press: Orlando, 1985.
38. Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653-2663.
39. Gallicchio, E.; Kubo, M. M.; Levy, R. M. J. Am. Chem. Soc. 1998, 120, 4526-4527.
40. Jencks, W. P. Catalysis in Chemistry and Enzymology, Dover Publications Inc.: New York, 1987.
41. Barone, G.; Castronuovo, G.; Doucas, D.; Ella, V.; Mattia, C. A. J. Phys. Chem. 1983, 87, 1931-1937.
42. Franks, F.; Reid, D. S.; Suggett, A. J. Solution Chem. 1973, 2, 99-103.
43. Galema, S. A.; Blandamer, M. J.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1990, 112, 9665-9666.
44. Hoiland, H.; Holvik, H. J. Solution Chem. 1978, 7, 587-592.
45. Miyajima, K.: Machida, K.; Nakagaki, M. Bull. Chem. Soc. Jpn. 1985, 58, 2595-2599.
46. Liu, Q.; Brady, J. W. J. Am. Chem. Soc. 1996, 118, 12276-12286.
47. Galema, S. A.; Holland, H. J. Phys. Chem. 1991, 95, 5321-5326.
48. Galema, S. A.; Blandamer, M. J.; Engberts, J. B. F. N. J. Org. Chem. 1992, 57, 1995-2001.
49. Grynkiewicz, G.; Fokl, I.; Szeja, W.; Fitak, H. J. Chem. Res. 1989, 152-156.
50. Excoffier, G.; Gagnaire, D.; Utille, J. P. Carbohydr. Res. 1975, 39, 368-373.
51. Haynes, L. J.; Neweth, F. H. Adv. Carbohydr. Chem. 1955, 10, 207-219.
52. Koeners, H. J.; de Kok, A. J.; Romers, C.; van Boom, J. H. Rec. Trav. Chim. Pays-Bas 1980, 99, 355-362.
53. Ballardie, F.; Capon, B.; Derek, J.; Sutherland, G.; Cocker, D.; Sinnott, M. J. Chem. Soc., Perkin Trans. 1 1973, 2418-2419.
54. Leatherbarrow, R. J. Gra-Fit, Version 2.0; Erithacus Software Ltd.: Staines, U.K., 1990.
55. March, J. Advanced Organic Chemistry; John Wiley & Sons: New York, 1985.
56. Emsly, J. W.; Feeney, J.; Sutcliffe, C. H. High-Resolution Nuclear Magnetic Resonance Spectroscopy; Pergamon Press: Oxford, 1966.
57. Taft, R. W. Prog. Phys. Org. Chem. 1983, 14, 247-269.
58. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry; Harper & Row: New York, 1987.
59. Cole, T. W. J.; Mayers, C. J.; Stock, L. M. J. Am. Chem. Soc. 1974, 96, 4555-4557.