A propos of glycosyl cations and the mechanism of chemical glycosylation; The current state of the art

Carbohydrate Research

Volumn 403, Issue , 2015, Pages 48-59

  Bohé, Luis ^a   Crich, David ^b  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

^b WAYNE STATE UNIVERSITY   (United States)

Author keywords

Counter ions; Hydrogen bonding; Kinetics; Oxocarbenium ions

Indexed keywords

ENZYME KINETICS; GLYCOSYLATION; HYDROGEN BONDS; REACTION INTERMEDIATES;

COUNTERIONS; GLYCOSYL; GLYCOSYLATION REACTIONS; OXOCARBENIUM; STATE OF THE ART;

IONS;

CATION; COUNTERION; ION; OXOCARBENIUM ION; UNCLASSIFIED DRUG; GLYCOSIDE;

ALKYLATION; ARTICLE; CONFORMATION; ENANTIOMER; GLYCOSYLATION; HYDROGEN BOND; ISOMER; KINETICS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOPHILICITY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; SPECTROSCOPY;

CARBOHYDRATE CONFORMATION; GLYCOSIDES; GLYCOSYLATION; KINETICS; MODELS, MOLECULAR; SPECTRUM ANALYSIS;

EID: 84961288920     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2014.06.020     Document Type: Review

References (104)

1. L. Bohé, and D. Crich C.R. Chim. 14 2011 3 16
2. A.J. Rhind-Tutt, and C.A. Vernon J. Chem. Soc. 1960 4637 4644
3. T.J. Lucas, and C. Schuerch Carbohydr. Res. 39 1975 39 45
4. R.U. Lemieux, K.B. Hendriks, R.V. Stick, and K. James J. Am. Chem. Soc. 97 1975 4056 4062
5. K. Saito, K. Ueoka, K. Matsumoto, S. Suga, T. Nokami, and J.-I. Yoshida Angew. Chem., Int. Ed. 50 2011 5153 5156
6. T. Nokami, K. Saito, and J.-I. Yoshida Carbohydr. Res. 363 2012 1 6
7. T. Nokami, R. Hayashi, Y. Saigusa, A. Shimizu, C.-Y. Liu, K.-K.T. Mong, and J.-I. Yoshida Org. Lett. 15 2013 4520 4523
8. Akien, G. R.; Subramaniam, B. In 245th ACS National Meeting and Exposition, New Orleans, 2013, p CARB-105.
9. Akien, G. R.; Subramaniam, B. In 247th ACS National Meeting and Exhibition Dallas, 2014, p CARB-96.
10. C. De Meo, C.E. Wallace, and S.A. Geringer Org. Lett. 14 2014 2676 2679
11. H. Satoh, H.S. Hansen, S. Manabe, W.F. van Gunsteren, and P.H. Hunenberger J. Chem. Theor. Comput. 6 2010 1783 1797
12. D.M. Whitfield Carbohydr. Res. 356 2012 191 195
13. D.M. Whitfield Carbohydr. Res. 356 2012 180 190
14. M. Huang, G.E. Garrett, N. Birlirakis, L. Bohé, D.A. Pratt, and D. Crich Nat. Chem. 4 2012 663 667
15. J. Chan, A. Tang, and A.J. Bennet J. Am. Chem. Soc. 134 2012 1212 1220
16. M. Heuckendorff, J. Bendix, C.M. Pedersen, and M. Bols Org. Lett. 16 2014 1116 1119
17. D.M. Whitfield Adv. Carbohydr. Chem. Biochem. 62 2009 83 159
18. M. Moumé-Pymbock, and D. Crich J. Org. Chem. 77 2012 8905 8912
19. M. Huang, P. Retailleau, L. Bohé, and D. Crich J. Am. Chem. Soc. 134 2012 14746 14749
20. B.S. Komarova, M.V. Orekhova, Y.E. Tsvetkov, and N.E. Nifantiev Carbohydr. Res. 384 2014 70 86
21. J. Kalikanda, and Z. Li J. Org. Chem. 76 2011 5207 5218
22. Y. Ma, G. Lian, Y. Li, and B. Yu Chem. Commun. 2011 7515 7517
23. H. Satoh, and T. Nukada Trends Glycosci. Glycobiol. 26 2014 11 27
24. C. Gouliaras, D. Lee, L. Chan, and M.S. Taylor J. Am. Chem. Soc. 133 2011 13926 13929
25. J.M. Wurst, G. Liu, and D.S. Tan J. Am. Chem. Soc. 133 2011 7916 7925
26. C. Denekamp, and Y. Sandlers J. Mass Spectrom. 40 2005 765 771
27. C. Denekamp, and Y. Sandlers J. Mass Spectrom. 40 2005 1055 1063
28. P.K. Kancharla, C. Navuluri, and D. Crich Angew. Chem., Int. Ed. 51 2012 11105 11109
29. L.O. Kononov, N.N. Malysheva, A.V. Orlova, A.I. Zinin, T.V. Laptinskaya, E.G. Kononova, and N.G. Kolotyrkina Eur. J. Org. Chem. 2012 1926 1934
30. X.-T. Zhang, Z.-Y. Gu, and G.-W. Xing Carbohydr. Res. 388 2014 1 7
31. K.L.M. Hoang, Y. Bai, X. Ge, and X.-W. Liu J. Org. Chem. 78 2013 5196 5204
32. M.L. Sinnott G.R.J. Thatcher, The Anomeric Effect and Associated Stereoelectronic Effects Vol. 539 1993 ACS Washington 97 113
33. M.L. Sinnott Adv. Phys. Org. Chem. 24 1988 113 204
34. I. Cumpstey Org. Biomol. Chem. 10 2012 2503 2508
35. B. Fraser-Reid, and C. Lopez Top. Curr. Chem. 301 2011 1 29
36. H.H. Jensen, C.M. Pedersen, and M. Bols Chem. Eur. J. 13 2007 7576 7582
37. Y. Okada, O. Nagata, M. Taira, and H. Yamada Org. Lett. 9 2007 2755 2758
38. Y. Okada, T. Mukae, K. Okajimia, M. Taira, M. Fujita, and H. Yamada Org. Lett. 9 2007 1573 1576
39. D.M. Smith, and K.A. Woerpel Org. Biomol. Chem. 4 2006 1195 1201
40. M.T.C. Walvoort, J. Dinkelar, L.J. van den Bos, G. Lodder, H.S. Overkleeft, J.D.C. CodeÍe, and G.A. van der Marel Carbohydr. Res. 345 2010 1252 1263
41. H.H. Jensen, and M. Bols Acc. Chem. Res. 39 2006 259 265
42. J. Rönnols, M.T.C. Walvoort, G.A. van der Marel, J.D.C. Codée, and G. Widmalm Org. Biomol. Chem. 11 2013 8127 8134
43. A.E. Christina, G.A. van der Marel, and J.D.C. Codée D.B. Werz, S. Vidal, Modern Synthetic Methods in Carbohydrate Chemistry; From Monosaccharides to Complex Glycoconjugates 2014 Wiley Weinheim 97 124
44. S. Crotti, and R. Adamo Curr. Org. Synth. 2013 501 524
45. B. Fraser-Reid, Z.C. Wu, W. Andrews, and E. Skowronski J. Am. Chem. Soc. 113 1991 1434 1435
46. C.W. Andrews, R. Rodebaugh, and B. Fraser-Reid J. Org. Chem. 61 1996 5280 5289
47. H.H. Jensen, M. Nordstrom, and M. Bols J. Am. Chem. Soc. 126 2004 9205 9213
48. M. Moumé-Pymbock, T. Furukawa, S. Mondal, and D. Crich J. Am. Chem. Soc. 135 2013 14249 14255
49. T. Gylling Frihed, M.T.C. Walvoort, J.D.C. CodeÍe, G.A. van der Marel, M. Bols, and C.M. Pedersen J. Org. Chem. 78 2013 2191 2205
50. X. Zhu, S.P. Kawatkar, Y. Rao, and G.-J. Boons J. Am. Chem. Soc. 128 2006 11948 11957
51. D. Crich, C.M. Pedersen, A.A. Bowers, and D.J. Wink J. Org. Chem. 72 2007 1553 1565
52. X.-Y. Liang, H.-C. Bin, and J.-S. Yang Org. Lett. 15 2013 2834 2837
53. P.K. Kancharla, and D. Crich J. Am. Chem. Soc. 135 2013 18999 19007
54. L. Corcilius, and R.J. Payne Org. Lett. 15 2013 5794 5797
55. J.P. Yasomanee, and A.V. Demchenko J. Am. Chem. Soc. 134 2012 20097 20102
56. Q.-W. Liu, H.-C. Bin, and J.-S. Yang Org. Lett. 15 2013 3974 3977
57. S.G. Pistorio, J.P. Yasomanee, and A.V. Demchenko Org. Lett. 16 2014 716 719
58. D. Crich, W. Cai, and Z. Dai J. Org. Chem. 65 2000 1291 1297
59. D. Crich, T. Hu, and F. Cai J. Org. Chem. 73 2008 8942 8953
60. D. Crich Acc. Chem. Res. 43 2010 1144 1153
61. B.S. Komarova, N.E. Ustyuzhania, Y.E. Tsvetkov, and N.E. Nifantiev D.B. Werz, S. Vidal, Modern Synthetic Methods in Carbohydrate Chemistry; From Monosaccharides to Complex Glycoconjugates 2014 Wiley Weinheim 125 160
62. S. Kaeothip, J.P. Yasomanee, and A.V. Demchenko J. Org. Chem. 77 2012 291 299
63. A.H. Haines Adv. Carbohydr. Chem. Biochem. 33 1976 11 109
64. K. Bock, J.F.B. Guzman, and S. Refn Carbohydr. Res. 232 1992 353 357
65. T. Nokami, Y. Nozaki, Y. Saigusa, A. Shibuya, S. Manabe, Y. Ito, and J.-I. Yoshida Org. Lett. 13 2011 1544 1547
66. T. Nokami Trends Glycosci. Glycobiol. 24 2012 203 214
67. S.S. Nigudkar, K.J. Stine, and A.V. Demchenko J. Am. Chem. Soc. 136 2014 921 923
68. S.-R. Lu, Y.H. Lai, J.-H. Chen, C.-Y. Liu, and K.-K.T. Mong Angew. Chem., Int. Ed. 50 2011 7315 7320
69. A.B. Ingle, C.-S. Chao, W.-C. Hung, and K.-K.T. Mong Org. Lett. 15 2013 5290 5293
70. S.K. Mulani, W.-C. Hung, A.B. Ingle, K.-S. Shiau, and K.-K.T. Mong Org. Biomol. Chem. 12 2014 1184 1197
71. D. Crich, and S. Sun J. Am. Chem. Soc. 119 1997 11217 11223
72. M.T.C. Walvoort, G.A. van der Marel, H.S. Overkleeft, and J.D.C. Codée Chem. Sci. 4 2013 897 906
73. S. Aubry, K. Sasaki, I. Sharma, and D. Crich Top. Curr. Chem. 301 2011 141 188
74. E. Raamat, K. Kaupmees, G. Ovsjannikov, A. Trummal, A. Kütt, J. Saame, I. Koppel, I. Kaljurand, L. Lipping, T. Rodima, V. Pihl, I.A. Koppel, and I. Leito J. Phys. Org. Chem. 26 2013 162 170
75. S. Brownstein, and A.E. Stillman J. Phys. Chem. 63 1959 2061 2062
76. K. Igarashi, T. Honma, and J. Irisawa Carbohydr. Res. 15 1970 329 337
77. D.N. Kevill, and G.M.L. Lin Tetrahedron Lett. 19 1978 949 952
78. H. Waldmann, G. Böhm, U. Schmid, and H. Röttele Angew. Chem., Int. Ed. Engl. 33 1994 1944 1946
79. S.J. Hasty, S.C. Ranade, and A.V. Demchenko Rep. Org. Chem. 4 2014 1 10
80. K. Matsumoto, K. Ueoka, S. Suzuki, S. Suga, and J.-I. Yoshida Tetrahedron 65 2009 10901 10907
81. H. Mayr, M. Breugst, and A.R. Ofial Angew. Chem., Int. Ed. 50 2011 6470 6505
82. S.-I. Kiyooka, D. Kaneno, and R. Fujiyama Tetrahedron 69 2013 4247 4258
83. A. Borovika, and P. Nagorny J. Carbohydr. Chem. 31 2012 255 283
84. A.-H.A. Chu, S.H. Nguyen, J.A. Sisel, A. Minciunescu, and C.S. Bennett Org. Lett. 15 2013 2566 2569
85. J.P. Issa, and C.S. Bennett J. Am. Chem. Soc. 136 2014 5740 5744
86. R. Eby, and C. Schuerch Carbohydr. Res. 34 1974 79 90
87. A. Kumar, V. Kumar, R.T. Dere, and R.R. Schmidt Org. Lett. 13 2011 3612 3615
88. A. Kumar, and R.R. Schmidt Eur. J. Org. Chem. 2012 2715 2719
89. T. Kimura, M. Sekine, D. Takahashi, and K. Toshima Angew. Chem., Int. Ed. 52 2013 12131 12134
90. Y. Geng, A. Kumar, H.M. Faidallah, H.A. Albar, I.A. Mhkalid, and R.R. Schmidt Angew. Chem., Int. Ed. 52 2013 10089 10092
91. E.I. Balmond, D.M. Coe, M.C. Galan, and E.M. McGarrigle Angew. Chem., Int. Ed. 51 2012 9152 9155
92. E.I. Balmond, M.C. Galan, and E.M. McGarrigle Synlett 2013 2335 2339
93. Z. Sun, G.A. Winschel, A. Borovika, and P. Nagorny J. Am. Chem. Soc. 134 2012 8074 8077
94. W.J. Wever, M.A. Cinelli, and A.A. Bowers Org. Lett. 15 2013 30 33
95. M. Spell, X. Wang, A.E. Wahba, E. Conner, and J. Ragains Carbohydr. Res. 369 2013 42 47
96. X. Yuan, S. Cheng, Y. Shi, and W. Xue Synthesis 46 2014 331 335
97. I. Cumpstey, and D.J. Crich Carbohydr. Chem 30 2011 469 485
98. M. Nakanishi, D. Takahashi, and K. Toshima Org. Biomol. Chem. 11 2013 5079 5082
99. V.K. Srivastava, and C. Schuerch Tetrahedron Lett. 20 1979 3269 3272
100. R.R. Schmidt Angew. Chem., Int. Ed. Engl. 25 1986 212 235
101. G. Hodosi, and P. Kováč J. Am. Chem. Soc. 119 1997 2335 2336
102. D. Zhu, K.N. Baryal, S. Adhikara, and J. Zhu J. Am. Chem. Soc. 136 2014 3172 3175
103. M.F. Cuccarese, J.J. Li, and G.A. O'Doherty D.B. Werz, S. Vidal, Modern Synthetic Methods in Carbohydrate Chemistry; From Monosaccharides to Complex Glycoconjugates 2014 Wiley Weinheim 1 28
104. P. Shi, M.C. Silva, H.-Y.L. Wang, B. Wu, N.G. Akhmedov, M. Li, P.J. Beuning, and G.A. O'Doherty ACS Med. Chem. Lett 3 2012 1086 1090