Mechanisms of glycopyranosyl and 5-thioglycopyranosyl transfer reactions in solution

Journal of the Chemical Society. Perkin Transactions 2

Volumn 2, Issue 7, 2002, Pages 1207-1222

  Bennet, Andrew J ^a   Kitos, Theresa E ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ENZYMES; HYDROLYSIS; ISOTOPES; SOLUTIONS;

GLYCOPYRANOSYL;

REACTION KINETICS;

EID: 0036019810     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b108446c     Document Type: Article

References (157)

1. J. F. Robyt Essentials of Carbohydrate Chemistry, Springer, New York, 1998.
2. J. F. Robyt Carbohydrate Chemistry, ed. G.-J. Boons Blackie Academic and Professional, London 1998.
3. J. F. Robyt Carbohydrate: Structures, Synthesis and Dynamics, ed. P. Finch Kluwer Academic Publishers, Dordrecht 1999.
4. J. F. Robyt Bioorganic Chemistry: Carbohydrates, ed. S. M. Hecht Oxford University Press, New York 1999.
5. G.-J. Boons and K. J. Hale Organic Synthesis with Carbohydrates, Sheffield Academic Press, Sheffield, 2000.
6. R. V. Stick Carbohydrates: The Sweet Molecules of Life, Academic Press, San Diego, 2001.
7. B. Capon Chem. Rev. 1969 69 407.
8. E. H. Cordes Prog. Phys. Org. Chem. 1967 4 1.
9. J. N. BeMiller Adv. Carbohydr. Chem. 1967 22 25.
10. C. A. Vernon Proc. R. Soc. London, Ser. B 1967 167 389.
11. T. H. Fife Acc. Chem. Res. 1974 74 581.
12. E. H. Cordes, H. G. Bull Chem. Rev. 1974 74 581.
13. M. L. Sinnott New Comprehensive Biochemistry: The Chemistry of Enzyme Action, ed. M. I. Page Elsevier, Amsterdam 1984, vol. 6, p. 389.
14. J. D. McCarter, S. G. Withers Curr. Opin. Struct. Biol. 1994 4 885.
15. A. White, D. R. Rose Curr. Opin. Struct. Biol. 1997 7 645.
16. G. Davies, M. L. Sinnott and S. G. Withers Comprehensive Biological Catalysis, ed. M. L. Sinnott Academic Press 1998, vol. 1, p. 119.
17. D. L. Zechel, S. G. Withers Acc. Chem. Res. 2000 33 11.
18. S. G. Withers Carbohydr. Polym. 2001 44 325.
19. P. J. Berti and K. S. E. Tanaka Adv. Phys. Org. Chem., 2002, 37, in press.
20. S. Winstein, B. Appel, R. Baker, A. Diaz Spec. Publ. Chem. Soc. 1965 19 109.
21. J. M. Harris Prog. Phys. Org. Chem. 1974 11 89.
22. D. J. Raber, J. M. Harris and P. v. R. Schleyer Ions and Ion Pairs in Organic Reactions, Vol. 2: Role of Ions and Ion Pairs in Chemical Reactions; ed. M. Swarc Wiley, New York 1974 247.
23. F. Wilkinson Chemical Kinetics and Reaction Mechanisms, Van Nostrand Reinhold, New York, 1980 17.
24. H. Maskill The Physical Basis of Organic Chemistry, Oxford University Press, Oxford, 1985 270.
25. J. P. Richard, W. P. Jencks J. Am. Chem. Soc. 1982 104 4689.
26. J. P. Richard, M. E. Rothenberg, W. P. Jencks J. Am. Chem. Soc. 1984 106 1361.
27. J. P. Richard J. Am. Chem. Soc. 1989 111 1455.
28. J. P. Richard, T. L. Amyes, M. M. Toteva Acc. Chem. Res. 2001 34 981.
29. T. L. Amyes, W. P. Jencks J. Am. Chem. Soc. 1989 111 7888.
30. R. A. McClelland, V. M. Kanagasabapathy, N. S. Banait, S. Steenken J. Am. Chem. Soc. 1991 113 1009.
31. R. A. McClelland, V. M. Kanagasabapathy, S. Steenken J. Am. Chem. Soc. 1988 110 6913.
32. J. P. Richard, M. M. Toteva, T. L. Amyes Org. Lett. 2001 3 2225.
33. F. J. Alvarez and R. L. Schowen Isotopes in Organic Chemistry, ed. E. Buncel and C. C. Lee Elsevier, Amsterdam 1987, vol. 7, pp. 1–60.
34. A. J. Kresge, R. A. More O’Ferrall and M. F. Powell Isotopes in Organic Chemistry, ed. E. Buncel and C. C. Lee Elsevier, Amsterdam 1987, vol. 7, pp. 177–273.
35. Commission on Physical Organic Chemistry, IUPAC J. Pure Appl. Chem. 1989 61 23.
36. R. Guthrie, W. P. Jencks Acc. Chem. Res. 1989 22 343.
37. A. D. McNaught Pure Appl. Chem. 1996 68 1919.
38. G. A. Olah J. Org. Chem. 2001 66 5943.
39. H. Yuasa, O. Hindsgaul, M. M. Palcic J. Am. Chem. Soc. 1992 114 5891 and references therein.
40. J. Rigaudy and S. P. Klesney Nomenclature of Organic Chemistry: Sections A, B, C, D, E, F and H, Pergamon Press, Oxford, 1979 53.
41. J. C. P. Schwarz J. Chem. Soc., Chem. Commun. 1973 505.
42. L. Hosie, P. J. Marshall, M. L. Sinnott J. Chem. Soc., Perkin Trans. 2 1984 1121.
43. S. Mehta, J. S. Andrews, B. D. Johnston, B. Svensson, B. M. Pinto J. Am. Chem. Soc. 1995 117 9783.
44. J. S. Andrews, T. Weimar, T. P. Frandsen, B. Svensson, B. M. Pinto J. Am. Chem. Soc. 1995 117 10799.
45. B. D. Johnston, B. M. Pinto J. Org. Chem. 1998 63 5797.
46. B. D. Johnston, B. M. Pinto Carbohydr. Res. 1998 310 17.
47. O. Tsuruta, H. Yuasa, H. Hashimoto, S. Kurono, S. Yazawa Bioorg. Med. Chem. Lett. 1999 9 1019.
48. T. Weimar, B. Stoffer, B. Svensson, B. M. Pinto Biochemistry 2000 39 300.
49. H. Yuasa, H. Hashimoto Trends Glycosci. Glycotechnol. 2001 13 31.
50. P. Deslongchamps The Anomeric Effect and Associated Stereoelectronic Effects, ed. G. R. J. Thatcher American Chemical Society, Washington D.C. 1992, ACS Symposium Series vol. 539, p. 26.
51. P. Deslongchamps Stereoelectronic Effects in Organic Chemistry, Pergamon Press, New York, 1983.
52. C. L. Perrin The Anomeric Effect and Associated Stereoelectronic Effects, ed. G. R. J. Thatcher American Chemical Society, Washington D.C. 1992, ACS Symposium Series vol. 539, p. 70.
53. C.L. Perrin Acc. Chem. Res. 2002 35 28.
54. M. L. Sinnott The Anomeric Effect and Associated Stereoelectronic Effects, ed. G. R. J. Thatcher American Chemical Society, Washington D.C. 1992, ACS Symposium Series vol. 539, p. 97.
55. S. Li, A. J. Kirby, P. Deslongchamps Tetrahedron Lett. 1993 34 7757.
56. P. Deslongchamps, P. G. Jones, A. J. Kirby, S. Kuusela, Y. Ma J. Chem. Soc., Perkin Trans. 2 1997 2621.
57. R. S. Brown, A. J. Bennet, H. Slebocka-Tilk Acc. Chem. Res. 1992 25 481.
58. C. L. Perrin, J. D. Thoburn J. Am. Chem. Soc. 1993 115 3140.
59. S. Wolfe, Z. Shi Isr. J. Chem. 2000 40 343 and references therein.
60. C. Armour, C. A. Bunton, S. Patai, L. H. Selman, C. A. Vernon J. Chem. Soc. 1961 412.
61. W. G. Overand, C. W. Rees, J. S. Sequeira J. Chem. Soc. 1962 3429.
62. R. J. Withey, E. Whalley Can. J. Chem. 1964 42 1456.
63. T. E. Timell, W. Enterman, F. Spencer, E. J. Soltes Can. J. Chem. 1965 43 2296.
64. A. J. Bennet, M. L. Sinnott J. Am. Chem. Soc. 1986 108 7287.
65. L. Melander and W. H. Saunders Reaction Rates of Isotopic Molecules, Wiley Interscience, New York–Chichester–Brisbane–Toronto, 1980 242.
66. L. Melander and W. H. Saunders Reaction Rates of Isotopic Molecules, Wiley Interscience, New York–Chichester–Brisbane–Toronto, 1980, pp. 174–180.
67. B. E. Lewis, V. L. Schramm J. Am. Chem. Soc. 2001 123 1327.
68. X. Huang, K. S. E. Tanaka, A. J. Bennet J. Am. Chem. Soc. 1997 119 11147.
69. X. Huang, C. Surry, T. Hiebert, A. J. Bennet J. Am. Chem. Soc. 1995 117 10614.
70. M. Eigen Angew. Chem., Int. Ed. Engl. 1964 3 1.
71. J. P. Richard, Y. Tsuji J. Am. Chem. Soc. 2000 122 3963.
72. J. P. Richard, W. P. Jencks J. Am. Chem. Soc. 1984 106 1373.
73. D. Indurugalla, A. J. Bennet J. Am. Chem. Soc. 2001 123 10889.
74. J. A. Barnes and I. H. Williams Organic Reactivity: Physical and Biological Aspects, ed. B. T. Golding R. J. Griffin and H. Maskill Royal Society of Chemistry, Cambridge 1995, pp. 437–443.
75. M. M. Toteva, J. P. Richard J. Am. Chem. Soc. 1996 118 11434.
76. B. Capon, D. Thacker J. Chem. Soc. B 1967 1010.
77. B. Capon, D. Thacker J. Chem. Soc. B 1967 1322.
78. P. J. Garegg, K.-J. Johansson, P. Konradsson, B. Lindberg, Z. Trumpakaj Carbohydr. Res. 2002 337 517.
79. K. J. Johansson, P. Konradsson, Z. Trumpakaj Carbohydr. Res. 2001 332 33.
80. A. Nowacki, K. Smiataczowa, R. Kasprzykowska, B. Dmochowska, A. Wiśniewski Carbohydr. Res. 2002 337 265.
81. The recommended IUPAC name for 2-deoxy- D -glucopyranose is 2-deoxy- D -arabino-hexopyranose (ref. 2).
82. J. Kaczmarek, M. Preyss, H. Lönnberg, J. Szafranek Carbohydr. Res. 1995 279 107.
83. J. Kaczmarek, Z. Kaczynski, Z. Trumpakaj, J. Szafranek, M. Bogalecka, H. Lönnberg Carbohydr. Res. 2000 325 16.
84. R. Wolfenden, X. Lu, G. Young J. Am. Chem. Soc. 1998 120 6814.
85. As the rate for this reaction does not vary significantly with changing the buffer concentrations, it is apparent that a single type of general catalysis is ineffective at promoting the water reaction.
86. J. L. Liras, E. V. Anslyn J. Am. Chem. Soc. 1994 116 2645.
87. J. L. Liras, V. M. Lynch, E. V. Anslyn J. Am. Chem. Soc. 1997 119 8191.
88. L. Hosie, P. J. Marshall, M. L. Sinnott J. Chem. Soc., Perkin Trans. 2 1984 1121.
89. T. L. Amyes, W. P. Jencks J. Am. Chem. Soc. 1989 111 7900.
90. E. L. Eliel, R. S. Ro J. Am. Chem. Soc. 1957 79 5995.
91. P. J. C. Fierens, P. Verschelden Bull. Soc. Chim. Belg. 1952 61 427.
92. J. Zhu, A. J. Bennet J. Am. Chem. Soc. 1998 120 3887.
93. J. Zhu, A. J. Bennet J. Org. Chem. 2000 65 4423.
94. D. T. H. Chou, J. N. Watson, A. A. Scholte, T. J. Borgford, A. J. Bennet J. Am. Chem. Soc. 2000 122 8357.
95. Acetic acid is about 100-fold less nucleophilic than water based on NOTs values, while water is about 500-fold less nucleophilic than acetate based on Swain–Scott n values (ref. 60).
96. K. A. Connors Chemical Kinetics: The Study of Reaction Rates in Solution, VCH Publishers Inc., New York, 1990.
97. T. L. Amyes, I. W. Stevens, J. P. Richard J. Org. Chem. 1993 58 6057.
98. E. Grunwald, S. Winstein J. Am. Chem. Soc. 1948 70 846.
99. A. H. Fainberg, S. Winstein J. Am. Chem. Soc. 1956 78 2770.
100. F. L. Schadt, P. v. R. Schleyer J. Am. Chem. Soc. 1973 95 7860.
101. T. W. Bentley, F. L. Schadt, P. v. R. Schleyer J. Am. Chem. Soc. 1972 94 992.
102. W. Schadt, T. W. Bentley, P. v. R. Schleyer J. Am. Chem. Soc. 1976 98 7667.
103. T. W. Bentley, P. v. R. Schleyer Adv. Phys. Org. Chem. 1977 14 32.
104. T. W. Bentley, G. Llewellyn Prog. Phys. Org. Chem. 1990 17 121.
105. D. N. Kevill, S. W. Anderson J. Am. Chem. Soc. 1986 108 1579.
106. J. March Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Wiley Interscience, New York, 1991, 4th edn., pp. 357–362.
107. R. Ta-Shma, Z. Rappoport Adv. Phys. Org. Chem. 1992 27 239 291.
108. T. L. Amyes, W. P. Jencks J. Am. Chem. Soc. 1988 110 3677.
109. M. Shimizu, H. Togo, M. Yokoyama Synthesis 1998 799.
110. M. Yokoyama Carbohydr. Res. 2000 327 5.
111. S. J. Williams, S. G. Withers Carbohydr. Res. 2000 327 27.
112. K. Toshirna Carbohydr. Res. 2000 327 15.
113. J. E. G. Barnett Carbohydr. Res. 1969 9 21.
114. N. S. Banait, W. P. Jencks J. Am. Chem. Soc. 1991 113 7951.
115. N. S. Banait, W. P. Jencks J. Am. Chem. Soc. 1991 113 7958.
116. Y. Zhang, J. Bommuswamy, M. L. Sinnott J. Am. Chem. Soc. 1994 116 7557.
117. M. L. Sinnott, W. P. Jencks J. Am. Chem. Soc. 1980 102 2026.
118. C. A. Bunton, D. R. Llewellyn, K. G. Oldham, C. A. Vernon J. Chem. Soc., C 1958 3588.
119. C. A. Bunton, E. Humeras J. Org. Chem. 1969 34 572.
120. S. G. Withers, D. J. MacLennan, I. P. Street Carbohydr. Res. 1986 154 127.
121. S. G. Withers, M. D. Percival, I. P. Street Carbohydr. Res. 1989 187 43.
122. B. A. Horenstein, M. Bruner J. Am. Chem. Soc. 1996 118 10371.
123. Calculated according to the equation ln (k12C/k14C)/1.9 = ln (k12C/k13C), ref. 32, pp. 74–75.
124. B. A. Horenstein, M. Bruner J. Am. Chem. Soc. 1998 120 1357.
125. A. N. Hall, S. Hollingshead, H. N. Rydon J. Chem. Soc. 1961 4290.
126. F. Van Wijnendaele, C. K. De Bruyne Carbohydr. Res. 1969 9 277.
127. C. K. De Bruyne, A. De Bock Carbohydr. Res. 1979 68 71.
128. R. L. Nath, H. N. Rydon Biochem. J. 1954 57 1.
129. A. J. Bennet, A. J. Davis, L. Hosie, M. L. Sinnott J. Chem. Soc., Perkin Trans. 2 1987 581.
130. S. Rosenberg, J. F. Kirsch Biochemistry 1981 20 3196.
131. M. Ashwell, X. Guo, M. L. Sinnott J. Am. Chem. Soc. 1992 114 10158.
132. Y.-Z. Lai, D. E. Ontto Carbohydr. Res. 1979 75 51.
133. D. Horton, A. E. Luetzow J. Chem. Soc., Chem. Commun. 1971 79.
134. C. C. Jones, M. L. Sinnott J. Chem. Soc., Chem. Commun. 1977 767.
135. D. Cocker, M. L. Sinnott J. Chem. Soc., Perkin Trans. 2 1975 1391.
136. M. N. Namchuk, J. D. McCarter, A. Becalski, T. Andrews, S. G. Withers J. Am. Chem. Soc. 2000 122 1270.
137. Thus, the assumption is that a change in ΔG‡ for formation of the cation (ΔΔG‡) is related to a change in the free energy for reaction of the cation, and ln (k1/k2) = constant × ln (τ2/τ1).
138. K. E. S. Dean, A. J. Kirby, I. V. Komarov J. Chem. Soc., Perkin Trans. 2 2002 337.
139. J. B. Lambert, S. M. Wharry Carbohydr. Res. 1983 115 33.
140. R. L. Girling, G. A. Jeffrey Acta Crystallogr., Sect. B 1973 29 1102.
141. J. B. Lambert, S. M. Wharry J. Org. Chem. 1981 46 3193.
142. N. A. Hughes, N. M. Munkombwe Carbohydr. Res. 1985 136 397.
143. B. M. Pinto and R. Y. N. Leung The Anomeric Effect and Associated Stereoelectronic Effects, ed. G. R. J. Thatcher American Chemical Society, Washington 1993 126.
144. V. Jagannadham, T. L. Amyes, J. P. Richard J. Am. Chem. Soc. 1993 115 8465.
145. F. Bernardi, C. I. G. Csizmadia, H. B. Schlegel, S. Wolfe Can. J. Chem. 1975 53 1144.
146. J. R. Larson, N. D. Epiotis J. Am. Chem. Soc. 1981 103 410.
147. Y. Apeloig, M. Karni J. Chem. Soc., Perkin Trans. 2 1988 625.
148. N. Buckley, N. J. Oppenheimer J. Org. Chem. 1996 61 8048.
149. R. L. Whistler, T. Van Es J. Org. Chem. 1963 28 2303.
150. B. D. Johnston, D. Indurugalla, B. M. Pinto, A. J. Bennet J. Am. Chem. Soc. 2001 123.
151. A. L. Allred, E. G. Rochow J. Inorg. Nucl. Chem. 1958 5 264.
152. L. Engman, J. Persson, C. M. Andersson, M. Berglund J. Chem. Soc., Parkin Trans. 2 1992 1309, in press.
153. S. Cottaz, C. Apparu, H. Driguez J. Chem. Soc., Perkin Trans. 1 1991 2235.
154. S. Wolfe, B. M. Pinto, V. Varma, R. Y. N. Leung Can. J. Chem. 1990 68 1051.
155. C. Scott, F. Grein Can. J. Chem. 1996 74 1221.
156. J. P. Richard Tetrahedron 1995 51 1535.
157. H. K. Chenault, L. F. Chafin J. Org. Chem. 1998 63 833.