Tetrafluorination of sugars as strategy for enhancing protein-carbohydrate affinity: Application to UDP-galp mutase inhibition

Chemistry - A European Journal

Volumn 20, Issue 1, 2014, Pages 106-112

  N'Go, Inès ^a   Golten, Samuel ^b   Ardá, Ana ^c   Cañada, Javier ^c   Jiménez Barbero, Jesús ^c   Linclau, Bruno ^b   Vincent, Stéphane P ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^c CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

Author keywords

carbohydrates; fluorine; inhibitors; NMR spectroscopy; tuberculosis

Indexed keywords

BENEFICIAL EFFECTS; CELL WALL BIOSYNTHESIS; COMPETITION ASSAYS; KEY ENZYMES; MYCOBACTERIUM TUBERCULOSIS; NATURAL SUBSTRATES; TUBERCULOSIS; UDP-GALACTOPYRANOSE;

BIOCHEMISTRY; BIOSYNTHESIS; CARBOHYDRATES; CORROSION INHIBITORS; FLUORINE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ENZYMES;

BACTERIAL PROTEIN; CARBOHYDRATE; DRUG DERIVATIVE; ENZYME INHIBITOR; FLUORINE; GALACTOSE; MUTASE; UDP GALACTOPYRANOSE MUTASE; UDP-GALACTOPYRANOSE MUTASE; URIDINE DIPHOSPHATE; URIDINE DIPHOSPHATE GALACTOFURANOSE;

ARTICLE; BIOCATALYSIS; CHEMISTRY; DRUG ANTAGONISM; ENZYMOLOGY; HALOGENATION; INHIBITORS; METABOLISM; MYCOBACTERIUM TUBERCULOSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN BINDING; TUBERCULOSIS;

CARBOHYDRATES; FLUORINE; INHIBITORS; NMR SPECTROSCOPY; TUBERCULOSIS;

BACTERIAL PROTEINS; BIOCATALYSIS; CARBOHYDRATES; ENZYME INHIBITORS; FLUORINE; GALACTOSE; HALOGENATION; INTRAMOLECULAR TRANSFERASES; MAGNETIC RESONANCE SPECTROSCOPY; MYCOBACTERIUM TUBERCULOSIS; PROTEIN BINDING; URIDINE DIPHOSPHATE;

EID: 84891494104     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201303693     Document Type: Article

References (68)

1. P. Sears, C.-H. Wong, Angew. Chem. 1999, 111, 2446-2471
2. Angew. Chem. Int. Ed. 1999, 38, 2300-2324
3. C.-Y. Wu, C.-H. Wong, Chem. Commun. 2011, 47, 6201-6207.
4. A. C. Weymouth-Wilson, Nat. Prod. Rep. 1997, 14, 99-110
5. J. M. Langenhan, B. R. Griffith, J. S. Thorson, J. Nat. Prod. 2005, 68, 1696-1711
6. J. S. Thorson, T. J. Hosted Jr., J. Jiang, J. B. Biggins, J. Ahlert, Curr. Org. Chem. 2001, 5, 139-167.
7. D. B. Werz, P. H. Seeberger, Chem. Eur. J. 2005, 11, 3194
8. P. H. Seeberger, D. B. Werz, Nature 2007, 446, 1046
9. Z. Tu, Y.-N. Lin, C.-H. Lin, Chem. Soc. Rev. 2013, 42, 4459-4475.
10. D. C. Koester, A. Holkenbrink, D. B. Werz, Synthesis 2010, 3217-3242
11. M. Agostino, M. S. Sandrin, P. E. Thompson, W. Farrugia, P. A. Ramsland, E. Yuriev, Expert Opin. Biol. Ther. 2011, 11, 211-224
12. A. Bernardi, A. C. J. Jiménez-Barbero, C. De Castro, T. Darbre, F. Fieschi, J. Finne, H. Funken, K.-E. Jaeger, M. Lahmann, T. K. Lindhorst, M. Marradi, P. Messner, A. Molinaro, P. Murphy, C. Nativi, S. Oscarson, S. Penadés, F. Peri, R. J. Pieters, O. Renaudet, J.-L. Reymond, B. Richichi, J. Rojo, F. Sansone, C. Schäffer, W. B. Turnbull, T. Velasco-Torrijos, S. Vidal, S. Vincent, T. Wennekes, H. Zuilhof, A. Imberty, Chem. Soc. Rev. 2013, 42, 4709-4727.
13. H. W. Kim, P. Rossi, R. K. Shoemaker, S. G. DiMagno, J. Am. Chem. Soc. 1998, 120, 9082-9083
14. J. C. Biffinger, H. W. Kim, S. G. DiMagno, ChemBioChem 2004, 5, 622-627.
15. J. Mecinovic, P. W. Snyder, K. A. Mirica, S. Bai, E. T. Mack, R. L. Kwant, D. T. Moustakas, A. Heroux, G. M. Whitesides, J. Am. Chem. Soc. 2011, 133, 14017-14026.
16. J. A. Olsen, D. W. Banner, P. Seiler, U. Obst-Sander, A. D′Arcy, M. Stihle, K. Müller, F. Diederich, Angew. Chem. 2003, 115, 2611-2615
17. Angew. Chem. Int. Ed. 2003, 42, 2507-2511
18. R. Paulini, K. Müller, F. Diederich, Angew. Chem. 2005, 117, 1820-1839
19. Angew. Chem. Int. Ed. 2005, 44, 1788-1805
20. K. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881-1886.
21. 1 conformation:, B. Linclau, S. Golten, M. Light, M. Sebban, H. Oulyadi, Carbohydr. Res. 2011, 346, 1129-1139.
22. A. Ioannou, E. Cini, R. S. Timofte, S. L. Flitsch, N. J. Turner, B. Linclau, Chem. Commun. 2011, 47, 11228-11230. For an example of affinity enhancement resulting from vicinal difluorination, see
23. I. P. Street, C. R. Armstrong, S. G. Withers, Biochemistry 1986, 25, 6021-6027.
24. P.-H. Tam, T. L. Lowary, Curr. Opin. Chem. Biol. 2009, 13, 618-625.
25. M. R. Richards, T. L. Lowary, ChemBioChem 2009, 10, 1920-1938.
26. F. Pan, M. Jackson, Y. Ma, M. McNeil, J. Bacteriol. 2001, 183, 3991-3998
27. E. C. Dykhuizen, J. F. May, A. Tongpenyai, L. L. Kiessling, J. Am. Chem. Soc. 2008, 130, 6706.
28. M. Soltero-Higgin, E. E. Carlson, T. D. Gruber, L. L. Kiessling, Nature Struct. Mol. Biol. 2004, 11, 539-543
29. C. Ansiaux, I. N′Go, S. P. Vincent, Chem. Eur. J. 2012, 18, 14860-14866
30. S. W. B. Fullerton, S. Daff, D. A. R. Sanders, W. J. Ingledew, C. Whitfield, S. K. Chapman, J. H. Naismith, Biochemistry 2003, 42, 2104-2109
31. J. M. Chad, K. P. Sarathy, T. D. Gruber, E. Addala, L. L. Kiessling, D. A. R. Sanders, Biochemistry 2007, 46, 6723-6732
32. M. Oppenheimer, A. L. Valenciano, K. Kizjakina, J. Qi, P. Sobrado, PLoS One 2012, 7, e 32918
33. M. B. Poulin, H. Nothaft, I. Hug, M. F. Feldman, C. M. Szymanski, T. L. Lowary, J. Biol. Chem. 2010, 285, 493-501
34. R. Dhatwalia, H. Singh, L. M. Solano, M. Oppenheimer, R. M. Robinson, J. F. Ellerbrock, P. Sobrado, J. J. Tanner, J. Am. Chem. Soc. 2012, 134, 18132-18138
35. H. G. Sun, M. W. Ruszczycky, W.-c. Chang, C. J. Thibodeaux, H.-w. Liu, J. Biol. Chem. 2012, 287, 4602-4608
36. G. Eppe, P. Peltier, R. Daniellou, C. Nugier-Chauvin, V. Ferrières, S. P. Vincent, Bioorg. Med. Chem. Lett. 2009, 19, 814-816
37. A. Caravano, P. Sinaÿ, S. P. Vincent, Bioorg. Med. Chem. Lett. 2006, 16, 1123-1125
38. A. Caravano, S. P. Vincent, Eur. J. Org. Chem. 2009, 1771-1780
39. Y. Yuan, X. Wen, D. A. R. Sanders, B. M. Pinto, Biochemistry 2005, 44, 14080-14089.
40. J. N. Barlow, J. S. Blanchard, Carbohydr. Res. 2000, 328, 473-480
41. Q. Zhang, H.-w. Liu, J. Am. Chem. Soc. 2001, 123, 6756-6766
42. J. C. Errey, M. C. Mann, S. A. Fairhurst, L. Hill, M. R. McNeil, J. H. Naismith, J. M. Percy, C. Whitfield, R. A. Field, Org. Biomol. Chem. 2009, 7, 1009-1016
43. A. Burton, P. Wyatt, G.-J. Boons, J. Chem. Soc. Perkin Trans. 1 1997, 2375-2383.
44. Y. Yuan, D. W. Bleile, X. Wen, D. A. R. Sanders, K. Itoh, H.-w. Liu, B. M. Pinto, J. Am. Chem. Soc. 2008, 130, 3157-3168.
45. J. C. Errey, B. Mukhopadhyay, K. P. Kartha, R. A. Field, Chem. Commun. 2004, 2706.
46. K. Itoh, Z. Huang, H.-w. Liu, Org. Lett. 2007, 9, 879-882.
47. C. Dalvit, A. Vulpetti, ChemMedChem 2011, 6, 104-114.
48. R. S. Timofte, B. Linclau, Org. Lett. 2008, 10, 3673-3676.
49. A. J. Boydell, V. Vinader, B. Linclau, Angew. Chem. 2004, 116, 5795-5797
50. Angew. Chem. Int. Ed. 2004, 43, 5677-5679.
51. X. H. Yao, D. W. Bleile, Y. Yuan, J. Chao, K. P. Sarathy, D. A. R. Sanders, B. M. Pinto, M. A. O'Neill, Proteins Struct. Funct. Bioinf. 2009, 74, 972-979.
52. M. Soltero-Higgin, E. E. Carlson, J. H. Phillips, L. L. Kiessling, J. Am. Chem. Soc. 2004, 126, 10532-10533.
53. A. Caravano, H. Dohi, P. Sinaÿ, S. P. Vincent, Chem. Eur. J. 2006, 12, 3114-3123
54. A. Caravano, D. Mengin-Lecreulx, J.-M. Brondello, S. P. Vincent, P. Sinaÿ, Chem. Eur. J. 2003, 9, 5888-5898.
55. M. Mayer, B. Meyer, Angew. Chem. 1999, 111, 1902-1906
56. Angew. Chem. Int. Ed. 1999, 38, 1784-1788
57. M. Mayer, B. Meyer, J. Am. Chem. Soc. 2001, 123, 6108-6117.
58. S. Kemper, M. K. Patel, J. C. Errey, B. G. Davis, J. A. Jones, T. D. W. Claridge, J. Magn. Reson. 2010, 203, 1-10
59. M. Mayer, T. L. James, J. Am. Chem. Soc. 2004, 126, 4453-4460.
60. S. G. Withers, Carbohydr. Polym. 2001, 44, 325-337
61. P. T. Nyffeler, S. G. Duron, M. D. Burkart, S. P. Vincent, C.-H. Wong, Angew. Chem. 2005, 117, 196-217
62. Angew. Chem. Int. Ed. 2005, 44, 192-212.
63. B. P. Rempel, M. B. Tropak, D. J. Mahuran, S. G. Withers, Angew. Chem. 2011, 123, 10565-10567
64. Angew. Chem. Int. Ed. 2011, 50, 10381-10383
65. M. Manoharan, A. Akinc, R. K. Pandey, J. Qin, P. Hadwiger, M. John, K. Mills, K. Charisse, M. A. Maier, L. Nechev, E. M. Greene, P. S. Pallan, E. Rozners, K. G. Rajeev, M. Egli, Angew. Chem. 2011, 123, 2332-2336
66. Angew. Chem. Int. Ed. 2011, 50, 2284-2288
67. S. L. Cobb, C. D. Murphy, J. Fluorine Chem. 2009, 130, 132-143.
68. X.-G. Li, S. DallAngelo, L. F. Schweiger, M. Zanda, D. O'Hagan, Chem. Commun. 2012, 48, 5247-5249.