The conformation of tetrafluorinated methyl galactoside anomers: Crystallographic and NMR studies

Carbohydrate Research

Volumn 346, Issue 9, 2011, Pages 1129-1139

  Linclau, Bruno ^a   Golten, Samuel ^a   Light, Mark ^a   Sebban, Muriel ^b   Oulyadi, Hassan ^b  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b UNIVERSITÉ DE ROUEN   (France)

Author keywords

Anomer; Chair conformation; Crystal structure; Fluorinated carbohydrate; NMR; Pyranose

Indexed keywords

ANOMER; CHAIR CONFORMATION; FLUORINATED CARBOHYDRATE; NMR; PYRANOSE;

CARBOHYDRATES; CRYSTAL STRUCTURE; DIHEDRAL ANGLE; FLUORINE; GLUCOSE; METHANOL; X RAY DIFFRACTION;

CONFORMATIONS;

FLUORINE DERIVATIVE; GALACTOSIDE; METHYL GROUP; TETRAFLUORINATED METHYL GALACTOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CONFORMATION; CRYSTALLOGRAPHY; FLUORINATION; FLUORINE NUCLEAR MAGNETIC RESONANCE; HYDROGEN BOND; HYDROPHILICITY; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION;

CARBOHYDRATE CONFORMATION; CRYSTALLOGRAPHY, X-RAY; GALACTOSIDES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR;

EID: 79955931791     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2011.04.007     Document Type: Article

References (78)

1. Reviews: (a) Cheng, Y.; Guo, A.-L.; Guo, D.-S. Curr. Org. Chem. 2010, 14, 977-999;
2. (b) Hein, M.; Miethchen, R. Adv. Org. Synth. 2006, 2, 381-429;
3. (c) Miethchen, R. J. Fluorine Chem. 2004, 125, 895-901;
4. (d) Dax, K.; Albert, M.; Ortner, J.; Paul, B. J. Carbohydr. Res. 2000, 327, 47-86;
5. (e) Dax, K.; Albert, M.; Ortner, J.; Paul, B. J. Curr. Org. Chem. 1999, 3, 287-307;
6. (f) Tsuchiya, T. Adv. Carbohydr. Chem. Biochem. 1990, 48, 91-277;
7. (g) Card, P. J. J. Carbohydr. Chem. 1985, 4, 451-487;
8. (h) Penglis, A. A. E. Adv. Carbohydr. Chem. Biochem. 1981, 38, 195-285.
9. (a) Glaudemans, C. P. J. Chem. Rev. 1991, 91, 25-33;
10. (b) Lemieux, R. U. Chem. Soc. Rev. 1989, 18, 347-374.
11. O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308-319.
12. (a) Vocadlo, D.; Davies, G. J.; Laine, R.; Withers, S. G. Nature 2001, 421, 835-838;
13. Reviews: (b) Zechel, D. L.; Withers, S. G. Acc. Chem. Res. 2000, 33, 11-18;
14. (c) Pongdee, R.; Liu, H.-W. Bioorg. Chem. 2004, 32, 393-437.
15. Wagner, S.; Mersh, C.; Hoffmann-Röder, A. Chem. Eur. J. 2010, 16, 7319-7330.
16. Examples: (a) Kim, H. W.; Rossi, P.; Schoemaker, R. K.; DiMagno, S. G. J. Am. Chem. Soc. 1998, 120, 9082-9083;
17. (b) Biffinger, J. C.; Kim, H. W.; DiMagno, S. G. ChemBioChem 2004, 5, 622-627;
18. (c) Boydell, A. J.; Vinader, V.; Linclau, B. Angew. Chem., Int. Ed. 2004, 43, 5677-5679;
19. (d) Timofte, R. S.; Linclau, B. Org. Lett. 2008, 10, 3673-3676;
20. (e) Linclau, B.; Boydell, A. J.; Timofte, R. S.; Brown, K. J.; Vinader, V.; Weymouth-Wilson, A. C. Org. Biomol. Chem. 2009, 7, 803-814;
21. (f) Bresciani, S.; Lebl, T.; Slawin, A. M. Z.; O'Hagan, D. Chem. Commun. 2010, 46, 5434-5436.
22. (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886;
23. (b) Zürcher, M.; Diederich, F. J. Org. Chem. 2008, 73, 4345-4361.
24. Dohi, H.; Périon, R.; Durka, M.; Bosco, M.; Roué, Y.; Moreau, F.; Grizot, S.; Ducruix, A.; Escaich, S.; Vincent, S. P. Chem. Eur. J. 2008, 14, 9530-9539.
25. (a) Gabius, H.-J.; Siebert, H.-C.; André, S.; Jiménez- Barbero, J.; Rüdiger, H. ChemBioChem 2004, 5, 740-764;
26. (b) Wormald, M. R.; Petrescu, A. J.; Pao, Y.-L.; Glithero, A.; Elliott, T.; Dwek, R. A. Chem. Rev. 2002, 102, 371-386;
27. (c) Rao, V. S. R.; Qasba, P. K.; Balaji, P. V.; Chandrasekaran, R. Conformation of Carbohydrates; Harwood Academic Publishers, 1998.
28. Kogelberg, H.; Solís, D.; Jiménez-Barbero, J. Curr. Opin. Struct. Biol. 2003, 13, 646-653.
29. García-Herrero, A.; Montero, E.; Muñoz, J. L.; Espinosa, J. F.; Vián, A.; García, J. L.; Asensio, J. L.; Cañada, F. J.; Jiménez-Barbero, J. J. Am. Chem. Soc. 2002, 124, 4804-4810.
30. Withers, S. G.; Street, I. P.; Rettig, S. J. Can. J. Chem. 1986, 64, 232-236.
31. Jeffrey, G. A. Acta Crystallogr., Sect. B 1990, 46, 89-103.
32. Takagi, S.; Jeffrey, G. A. Acta Crystallogr., Sect. B 1979, 35, 902-906. The α-anomer crystallized as a monohydrate.
33. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. II 1987, S1-S19.
34. (a) Jeffrey, G. A.; Pople, J. A.; Radom, L. Carbohydr. Res. 1972, 25, 117-131;
35. (b) Berman, H. M.; Chu, S. S. C.; Jeffrey, G. A. Science 1967, 157, 1576-1577;
36. (c) Schleifer, L.; Senderowitz, H.; Aped, P.; Tartakovsky, E.; Fuchs, B. Carbohydr. Res. 1990, 206, 21-39.
37. Zhang, W.; Oliver, A. G.; Serianni, A. S. Acta Crystallogr., Sect. C 2010, 66, o496-o498.
38. Kim, S. H.; Jeffrey, G. A. Acta Crystallogr. 1967, 22, 537-545.
39. (a) Dunitz, J. D. ChemBioChem 2004, 5, 614-621;
40. (b) Hunter, L.; Slawin, A. M. Z.; Kirsch, P.; O'Hagan, D. Angew. Chem., Int. Ed. 2007, 46, 7887-7890.
41. (a) Mehta, G.; Sen, S. Eur. J. Org. Chem. 2010, 3387-3394;
42. (b) Bernet, B.; Vasella, A. Helv. Chim. Acta 2007, 90, 1874-1888;
43. (c) Sardinha, J.; Guieu, S.; Deleuze, A.; Fernández-Alonso, M. C.; Rauter, A. P.; Sinaÿ, P.; Marrot, J.; Jiménez-Barbero, J.; Sollogoub, M. Carbohydr. Res. 2007, 342, 1689-1703;
44. (d) Miles, J. A. L.; Mitchell, L.; Percy, J. M.; Singh, K.; Uneyama, E. J. Org. Chem. 2007, 72, 1575-1587.
45. (a) Cremer, D.; Pople, J. A. J. Am. Chem. Soc. 1975, 97, 1354-1358;
46. (b) Jeffrey, G. A.; Yates, J. H. Carbohydr. Res. 1979, 74, 319-322;
47. (c) Köll, P.; Saak, W.; Pohl, S.; Steiner, B.; Koós, M. Carbohydr. Res. 1994, 265, 237-248;
48. (d) Boeyens, J. C. A. J. Chem. Crystallogr. 1978, 8, 317-320.
49. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13.
50. Review: Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76.
51. For a rare example of a galactose derivative having a gg conformer that is not stabilized by intramolecular but by intermolecular hydrogen bonding: Ojala, C. R.; Ostman, J. M.; Ojala, W. H. Carbohydr. Res. 2002, 337, 21-29.
52. Laurence, C.; Brameld, K. A.; Graton, J.; Le Questrel, J.-Y.; Renault, E. J. Med. Chem. 2009, 52, 4073-4086.
53. (a) Thalladi, V. R.; Weiss, H.-C.; Bläser, D.; Boese, R.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 8702-8710;
54. (b) Dunitz, J. D.; Schweizer, W. B. Chem. Eur. J. 2006, 12, 6804-6815;
55. (c) Reichenbächer, K.; Süss, H. I.; Hulliger, J. Chem. Soc. Rev. 2005, 34, 22-30.
56. Review: Duus, J. Ø.; Gotfredsen, C. H.; Bock, K. Chem. Rev. 2000, 100, 4589-4614.
57. Reviews: (a) Michalik, M.; Hein, M.; Frank, M. Carbohydr. Res. 2000, 327, 185-218;
58. (b) Csuk, R.; Glänzer, B. I. Adv. Carbohydr. Chem. Biochem. 1988, 46, 73-177;
59. (c) Ref. 1g.
60. (a) Lemieux, R. U.; Stevens, J. D. Can. J. Chem. 1965, 43, 2059-2070;
61. (b) Lemieux, R. U.; Kullnig, R. K.; Bernstein, H. J.; Schneider, W. G. J. Am. Chem. Soc. 1958, 80, 6098-6105;
62. (c) Hall, L. D. Tetrahedron Lett. 1964, 23, 1457-1460.
63. Wray, V. J. Chem. Soc., Perkin Trans. II 1976, 1598-1605.
64. Rozen, S.; Zamir, D. J. Org. Chem. 1991, 56, 4695-4700.
65. Martin, J. A.; Chauvin, M.; Levisalles, J. Tetrahedron Lett. 1966, 25, 2879-2882.
66. (a) Hall, L. D.; Johnson, R. N.; Adamson, J.; Foster, A. B. Chem. Commun. 1970, 463-464;
67. (b) Kurtkaya, S.; Barone, V.; Peralta, J. E.; Contreras, R. H.; Snyder, J. P. J. Am. Chem. Soc. 2002, 124, 9702-9703;
68. (c) Provasi, P. F.; Sauer, S. P. A. J. Chem. Theory Comput. 2006, 2, 1019-1027; Review:
69. (d) Coxon, B. Adv. Carbohydr. Chem. Biochem. 2009, 62, 17-82.
70. Roslund, M. U.; Klika, K. D.; Lehtilä, R. L.; Tähtinen, P.; Sillanpää, R.; Leino, R. J. Org. Chem. 2004, 69, 18-25.
71. (a) For examples of such an intramolecular F···OH coupling: Ref. 20b.;
72. (b) Biamonte, M. A.; Vasella, A. Helv. Chim. Acta 1998, 81, 695-717;
73. (c) Nakai, K.; Takagi, Y.; Tsuchiya, T. Carbohydr. Res. 1999, 316, 47-57;
74. (d) Takagi, Y.; Sohtome, H.; Tsuchiya, T.; Umezawa, S. J. Antibiot. 1992, 45, 355-362.
75. COLLECT data collection software, Nonius B.V., 1998.
76. Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. In Methods in Enzymology In Macromolecular Crystallography, Part A; Carter, C. W., Jr., Sweet, R. M., Eds.; Academic Press, 1997; Vol. 276, pp 307-326.
77. Sheldrick, G. M. SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10.
78. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122.