Plausible transition states for glycosylation reactions

Carbohydrate Research

Volumn 356, Issue , 2012, Pages 180-190

  Whitfield, Dennis M ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

Density functional theory; Glycosylation; Oxacarbenium ion; Transition states

Indexed keywords

ANOMERICS; COMPUTATIONAL APPROACH; DENSITY FUNCTIONAL THEORY CALCULATIONS; GLYCOSYL DONORS; GLYCOSYLATION REACTIONS; GLYCOSYLATIONS; HYPOTHETICAL MODELS; NUCLEOPHILIC ATTACK; TRANSITION STATE; TRIFLATES;

CHLORINE; COMPUTATIONAL METHODS; DENSITY FUNCTIONAL THEORY; ESTERIFICATION; METHANOL;

GLYCOSYLATION;

CARBON; LITHIUM ION; METHANOL; NUCLEOPHILE; OXYGEN;

BIOLOGY; CHEMICAL BOND; COMPLEX FORMATION; CONFERENCE PAPER; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; GLYCOSYLATION; IONIZATION; MOLECULAR MODEL; PRIORITY JOURNAL; REACTION OPTIMIZATION; STEREOCHEMISTRY;

GLYCOSIDES; GLYCOSYLATION; LITHIUM; MESYLATES; METHANOL; METHYLENE CHLORIDE; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXYGEN; QUANTUM THEORY; STEREOISOMERISM; THERMODYNAMICS;

EID: 84862329935     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2012.03.040     Document Type: Conference Paper

References (101)

1. D.M. Whitfield H. Derek, Adv. Carbohydr. Chem. Biochem. Vol. 62 2009 Academic Press 83 159
2. Premathilake, H.D.; Demchenko, A.V. In Reactivity Tuning in Oligosaccharide Assembly, Fraser-Reid, B., López, J. C. Eds.; Top. Curr. Chem. 2011, 301, 189-122.
3. L. Bohé, and D. Crich C R Chim. 14 2011 3 16
4. Hsu, C.-H.; Hung, S.-C.; Wu, C.-Y.; Wong, C.-H. Angew. Chem., Int. Ed. 2011, 50, 11872-11923.
5. D.P. Galonić, and D.Y. Gin Nature 446 2007 1000 1007
6. M. Sato, H. Yamataka, Y. Komeiji, Y. Mochizuki, T. Ishikawa, and T. Nakano J. Am. Chem. Soc. 130 2008 2396 2397
7. Aubry, S.; Sasaki, K.; Sharma, I.; Crich, D. In Reactivity Tuning in Oligosaccharide Assembly, Fraser-Reid, B., López, J. C. Eds.; Top. Curr. Chem. 2011, 301, 141-188.
8. Some examples without promoters K.J. Jensen J. Chem. Soc., Perkin Trans. 1 2002 2219 2233
9. J. Gildersleeve, R.A. Pascal, and D. Kahne J. Am. Chem. Soc. 120 1998 5961 5969
10. X. Huang, L. Huang, H. Wang, and X.-S. Ye Angew. Chem., Int. Ed. 43 2004 5221 5224
11. J.D. Codée, R.E. Litjens, R. den Heeten, H.S. Overkleeft, J.H. van Boom, and G.A. van der Marel Org. Lett. 5 2003 1519 1522
12. A.V. Demchenko, N.N. Malysheva, and C. De Meo Org. Lett. 5 2003 455 458
13. P. Pornsuriyasak, and A.V. Demchenko Chem. Eur. J. 12 2006 6630 6646
14. K.S. Kim, and H.B. Jeon Chem. Rec. 8 2008 46 65
15. J. Kalikanda, and Z. Li J. Org. Chem. 76 2011 5207 5218
16. D. Crich Acc. Chem. Res. 43 2010 1144 1153
17. M.T.C. Walvoort, J. Dinkelaar, L.J. van den Bos, G. Lodder, H.S. Overkleeft, J.D. Codée, and G.A. van der Marel Carbohydr. Res. 345 2010 1252 1263
18. M.G. Beaver, S.B. Billings, and K.A. Woerpel Eur. J. Org. Chem. 2008 771 781
19. C. Denekamp, and Y. Sandlers J. Mass Spectrom. 40 2005 765 771
20. C. Denekamp, and Y. Sandlers J. Mass Spectrom. 40 2005 1055 1063
21. V. Kovacik, J. Hirsch, D. Thölmann, and H.-F. Grützmacher Org. Mass. Spectrom. 26 1991 1085 1088
22. Some examples R.J. Woods, C.W. Andrews, and J.P. Bowen J. Am. Chem. Soc. 114 1992 859 864
23. D. Liu, M.R. Nimlos, D.K. Johnson, M.E. Himmel, and X. Qian J. Phys. Chem. A 2010 12936 12944
24. V.L. Schramm J. Biol. Chem. 284 2009 32201 32208
25. A. Ardèvol, and C. Rovira Angew. Chem., Int. Ed. 50 2011 10902 10906
26. K. Saito, K. Ueoka, K. Matsumoto, S. Suga, T. Nokami, and J. Yoshida Angew. Chem., Int. Ed. 50 2011 5153 5156
27. M.G. Beaver, and K.A. Woerpel J. Org. Chem. 75 2010 1107 1118
28. M.T.C. Walvoort, G. Lodder, H.S. Overkleeft, J.D.C. Codée, and G.A. van der Marel J. Org. Chem. 75 2010 7990 8002
29. C. Bucher, and R. Gilmour Angew. Chem., Int. Ed. 49 2010 8724 8728
30. Some attempts P.P. Deshpande, B.A. Ellsworth, F.G. Buono, A. Pullockaran, J. Singh, T.P. Kissick, M.-H. Huang, H. Lobinger, T. Denzel, and R.H. Mueller J. Org. Chem. 72 2007 9746 9749
31. Y. Okada, O. Nagata, M. Taira, and H. Yamada Org. Lett. 9 2007 2755 2758
32. Z. Li, L. Zhu, and J. Kalikanda Tetrahedron. Lett. 52 2011 5629 5632
33. J. Dinkelaar, A.R. de Jong, R. van Meer, M. Somers, G. Lodder, H.S. Overkleeft, J.D. Codée, and G.A. van der Marel J. Org. Chem. 74 2009 4982 4991
34. T. Furukawa, H. Hinou, K. Shimawaki, and S-.I. Nishimura Tetrahedron Lett. 52 2009 5567 5570
35. T.M. Gloster, P. Meloncelli, R.V. Stick, D. Zechel, A. Vasella, and G.J. Davies J. Am. Chem. Soc. 129 2007 2345 2354
36. S. Fushinobu, B. Mertz, A.D. Hill, M. Hidaka, M. Kitaoka, and P.J. Reilly Carbohydr. Res. 343 2008 1023 1033
37. Horenstein, B. A. In Transition State Modeling for Catalysis; Truhlar, D. G.; Morokuma, K. Eds.; ACS Symp. Ser. 1999; Vol. 721, 411-423.
38. H.J. Lee, L.L. Lairson, J.R. Rich, E. Lameignere, W.W. Wakarchuk, S.G. Withers, and N.C.J. Strynadka J. Biol. Chem. 286 2011 35922 35932
39. A.P. Bento, and F.M. Bickelhaupt J. Org. Chem. 73 2008 7290 7299
40. N.S. Banait, and W.P. Jencks J. Am. Chem. Soc. 113 1991 7951 7958
41. T.L. Amyes, and W.P. Jencks J. Am. Chem. Soc. 111 1989 7888 7900
42. C. Chiappe, G.L. Moro, and P. Munforte Tetrahedron 53 1997 10471 10478
43. J. Zhu, and A.J. Bennet J. Am. Chem. Soc. 120 1998 3887 3893
44. G.A. Olah J. Org. Chem. 66 2001 5943 5957
45. D.A. Forsyth, V.M. Osterman, and J.R. DeMember J. Am. Chem. Soc. 107 1985 818 822
46. R.G. Silva, A.S. Murkin, and V.L. Schramm Proc. Natl. Acad. Sci. 108 2011 18661 18665
47. M. Sinnott Carbohydrate Chemistry and Biochemistry: Structure and Mechanism 2007 Royal Society of Chemistry
48. P.K. Qasba, B. Ramakrishnan, and E. Boeggeman Trends Biochem. Sci. 30 2005 53 62
49. D.M.A. Guérin, M.B. Lascombe, M. Costabel, H. Souchon, V. Lamzin, P. Béguin, and P.M. Alzari J. Mol. Biol. 316 2002 1061 1069
50. V.M.A. Ducros, D.L. Zechel, G.N. Murshudov, H.J. Gilbert, L. Szabó, D. Stoll, S.G. Withers, and G.J. Davies Angew. Chem., Int. Ed. 41 2002 2824 2827
51. C.B. Barnett, K.A. Wilkinson, and K.J. Naidoo J. Am. Chem. Soc. 132 2010 12800 12803
52. G.J. Davies, A. Planas, and C. Rovira Acc. Chem. Res. 45 2012 308 316
53. G.I. Csonka, and J. Kaminsky J. Chem. Theor. Comput. 7 2011 988 997
54. T. Nukada, A. Bérces, L.-J. Wang, M.Z. Zgierski, and D.M. Whitfield Carbohydr. Res. 340 2005 841 852
55. A.R. Ionescu, D.M. Whitfield, M.Z. Zgierski, and T. Nukada Carbohydr. Res. 341 2006 2912 2920
56. Some Possible Types of Interactions K.P. Gierszal, J.G. Davis, M.D. Hands, D.S. Wilcox, L.V. Slipchenko, and D. Ben-Amotz J. Phys. Chem. Lett. 2 2011 2930 2933
57. Y.V. Nelyubina, P.Y. Barzilovich, M.Y. Antipin, S.M. Aldoshin, and K.A. Lyssenko ChemPhysChem 12 2011 2895 2898
58. Z. Li Carbohydr. Res. 345 2010 1952 1957
59. Y.-P. Cheng, H.-T. Chen, and C.-C. Lin Tetrahedron Lett. 43 2002 7721 7723
60. J.P. Simons, R.A. Jockusch, P. Çarçabal, I. Hünig, R.T. Kroemer, N.A. Macleod, and L.C. Snoek Int. Rev. Phys. Chem. 24 2005 489 531
61. D.M. Whitfield Carbohydr. Res. 342 2007 1726 1740
62. L. Petersen, A. Ardèvol, C. Rovira, and P.J. Reilly J. Phys. Chem. B 113 2009 7331 7339
63. M.E.S. Soliman, G.D. Ruggiero, J.J.R. Pernía, I.R. Greig, and I.H. Williams Org. Biomol. Chem. 7 2009 460 468
64. H. Dong, M.R. Nimlos, M.E. Himmel, D.K. Johnson, and X. Qian J. Phys. Chem. A 113 2009 8577 8585
65. L. Amorim, F. Marcelo, C. Rousseau, L. Nieto, J. Jiménez-Barbero, J. Marrot, A.P. Rauter, M. Sollogoub, M. Bols, and Y. Blériot Chem. Eur. J. 17 2011 7345 7356
66. J.F. Stoddart Stereochemistry of Carbohydrates 1971 Wiley-interscience New York
67. M. Ji, R.W. Hartsock, Z. Sun, and K.J. Gaffney J. Phys. Chem. B 115 2011 11399 11408
68. D. Farcaşiu, and D. Hâncu J. Am. Chem. Soc. 121 1999 7173 7181
69. + as promoter H. Waldmann, G. Böhm, U. Schmid, and H. Röttele Angew. Chem., Int. Ed. 33 1994 1944 1946
70. A. Lubineau, and B. Drouillat J. Carbohydr. Chem. 16 1997 1179 1186
71. S.-H. Yu, G.D. Sprott, C.J. Dicaire, and D.M. Whitfield Carbohydr. Res. 345 2010 214 229
72. D.J. Cox, M.D. Smith, and A.J. Fairbanks Org. Lett. 12 2010 1452 1455
73. S. Sun, Q. Ma, X.-B. Meng, Q. Li, S.-C. Li, H.-Q. Huang, and Z-.J. Li J. Chin. Pharm. Sci. 20 2011 549 556
74. M.C. Galan, K. Jouvin, and D. AlvarezDorta Carbohydr Res. 345 2010 45 49
75. For example C.S. Chao, Y.F. Yen, W.C. Hung, and K.K.T. Mong Adv. Synth. Catal. 353 2011 879 884
76. C.S. Chao, C.W. Li, M.C. Chen, S.S. Chang, and K.K.T. Mong Chem. Eur. J. 15 2009 10972 10982
77. C.S. Chao, C.-Y. Lin, S. Mulani, W.-C. Hing, and K.K.T. Mong Chem. Eur. J. 17 2011 12193 12202
78. R. Fujiwara, and S. Horito Carbohydr. Res. 346 2011 2098 2103
79. For example Y. Geng, and X.-S. Ye Synlett 2010 2506 2512
80. J. Park, S. Kawatkar, J.-H. Kim, and G.-J. Boons Org. Lett. 9 2007 1959 1962
81. W. Gilbert, Y. Zeng, and X. Huang Sci. Chin. Chem. 54 2011 66 73
82. H. Satoh, H.S. Hansen, S. Manabe, W.F. van Gunsteren, and P.H. Hünenberger J. Chem. Theory Comput. 6 2010 1783 1797
83. S. Sun, Q. Ma, X.B. Meng, Q. Li, S.C. Li, H.Q. Huang, and Z.J. Li J. Chin. Pharm. Sci. 20 2011 549 556
84. M.C. Galan, K. Jouvin, and D. Alvarez-Dorta Carbohydr. Res. 345 2010 45 49
85. C.C. Pye, T. Ziegler, E. van Lenthe, and J.N. Louwen Can. J. Chem. 87 2009 790 797
86. D. Crich, and V. Dudkin Tetrahedron Lett. 41 2000 5643 5646
87. D. Crich, and P. Jayalath Org. Lett. 7 2005 2277 2280
88. D. Crich, P. Jayalath, and T.K. Hutton J. Org. Chem. 71 2006 3064 3070
89. S.S. Lee, S.Y. Hong, J.C. Errey, A. Izumi, G.J. Davies, and B.G. Davis Nature Chem. Biol. 7 2011 631 638
90. A. Chaikuad, D.S. Froese, G. Berridge, F. von Delft, U. Oppermann, and W.W. Yue Proc. Natl. Acad. Sci. 108 2011 21018 21033
91. L. Perić-Hassler, H.S. Hanse, R. Baron, and P.H. Hünenberger Carbohydr. Res. 345 2010 1781 1801
92. C.B. Barnett, K.A. Wilkinson, and K.J. Naidoo J. Am. Chem. Soc. 133 2011 19474 19482
93. See 9d, 34b and 17e.
94. Dong, H.; Qian, X. In Computational Modeling in Lignocellulosic Biofuel Production Am. Chem. Soc. Symp. Ser. 2010, pp 1-15.
95. J. Chan, A. Tang, and A.J. Bennet J. Am. Chem. Soc. 134 2012 1212 1220
96. E.J. Baerends, D.E. Ellis, and P. Ros Chem. Phys. 2 1973 41 51
97. G. te Velde, and E.J. Baerends J. Comput. Phys. 99 1992 84 98
98. C. Fonseca Guerra, J.G. Snijders, G. te Velde, and E.J. Baerends Theor. Chim. Acta 99 1998 391 403
99. L. Versiuis, and T.J. Ziegler Chem. Phys. 88 1988 322 328
100. L. Fan, and T. Ziegler J. Chem. Phys. 96 1992 9005 9012
101. M. Hricovíni Carbohydr. Res. 341 2006 2575 2580