Fluorosugar chain termination agents as probes of the sequence specificity of a carbohydrate polymerase

Journal of the American Chemical Society

Volumn 134, Issue 15, 2012, Pages 6552-6555

  Brown, Christopher D ^a,b   Rusek, Max S ^a   Kiessling, Laura L ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b UNIVERSITY OF WISCONSIN SCHOOL OF MEDICINE AND PUBLIC HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE POLYMERS; CELL WALLS; CHAIN TERMINATIONS; DIASTEREOMERS; GALACTANS; GLYCOSYLTRANSFERASES; KINETICALLY CONTROLLED; MYCOBACTERIUM TUBERCULOSIS; NATURALLY OCCURRING; SEQUENCE PATTERNS; SEQUENCE SPECIFICITY;

CARBOHYDRATES; ENZYMES;

POLYMERS;

CARBOHYDRATE DERIVATIVE; CARBOHYDRATE POLYMERASE; GALACTAN; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL CELL WALL; CATALYST; DIASTEREOISOMER; MECHANICAL PROBE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; POLYMERIZATION; SYNTHESIS;

CARBOHYDRATE SEQUENCE; GALACTOSYLTRANSFERASES; GLYCOSYLTRANSFERASES; MYCOBACTERIUM TUBERCULOSIS; POLYMERIZATION; POLYSACCHARIDES; REPETITIVE SEQUENCES, NUCLEIC ACID;

EID: 84859977215     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja301723p     Document Type: Article

References (39)

1. Ross, P.; Mayer, R.; Benziman, M. Microbiol. Rev. 1991, 55, 35
2. Weigel, P. H.; DeAngelis, P. L. J. Biol. Chem. 2007, 282, 36777
3. Raetz, C. R. H.; Whitfield, C. Annu. Rev. Biochem. 2002, 71, 635
4. Brennan, P. J.; Nikaido, H. Annu. Rev. Biochem. 1995, 64, 29
5. Sauvage, E.; Kerff, F.; Terrak, M.; Ayala, J. A.; Charlier, P. FEMS Microbiol. Rev. 2008, 32, 234
6. Woodward, R.; Yi, W.; Li, L.; Zhao, G.; Eguchi, H.; Sridhar, P. R.; Guo, H.; Song, J. K.; Motari, E.; Cai, L.; Kelleher, P.; Liu, X.; Han, W.; Zhang, W.; Ding, Y.; Li, M.; Wang, P. G. Nat. Chem. Biol. 2010, 6, 418
7. McCandless, E. L.; Craigie, J. S. Annu. Rev. Plant Physiol. 1979, 30, 41
8. Shen, G.-J.; Datta, A. K.; Izumi, M.; Koeller, K. M.; Wong, C.-H. J. Biol. Chem. 1999, 274, 35139
9. May, J. F.; Levengood, M. R.; Splain, R. A.; Brown, C. D.; Kiessling, L. L. Biochemistry 2012, 51, 1148
10. Vionnet, J.; Vann, W. F. Glycobiology 2007, 17, 735
11. Besra, G. S.; Khoo, K. H.; McNeil, M. R.; Dell, A.; Morris, H. R.; Brennan, P. J. Biochemistry 1995, 34, 4257
12. Rose, N. L.; Completo, G. C.; Lin, S. J.; McNeil, M.; Palcic, M. M.; Lowary, T. L. J. Am. Chem. Soc. 2006, 128, 6721
13. Hagen, K.; Hedberg, K. J. Am. Chem. Soc. 1973, 95, 8263
14. Guvench, O.; MacKerell, A. D. J. Phys. Chem. A 2006, 110, 9934
15. OHagan, D. Chem. Soc. Rev. 2008, 37, 308
16. Withers, S. G.; Street, I. P.; Bird, P.; Dolphin, D. H. J. Am. Chem. Soc. 1987, 109, 7530
17. Pouilly, S.; Bourgeaux, V.; Piller, F.; Piller, V. ACS Chem. Biol. 2012, 10.1021/cb200511t
18. Barthel, S. R.; Antonopoulos, A.; Cedeno-Laurent, F.; Schaffer, L.; Hernandez, G.; Patil, S. A.; North, S. J.; Dell, A.; Matta, K. L.; Neelamegham, S.; Haslam, S. M.; Dimitroff, C. J. J. Biol. Chem. 2011, 286, 21717
19. Peltier, P.; Daniellou, R.; Nugier-Chauvin, C.; Ferrières, V. Org. Lett. 2007, 9, 5227
20. Peltier, P.; Belánová, M.; Dianiaková, P.; Zhou, R.; Zheng, R. B.; Pearcey, J. A.; Joe, M.; Brennan, P. J.; Nugier-Chauvin, C.; Ferrières, V.; Lowary, T. L.; Daniellou, R.; Mikusová, K. Chem. Biol. 2010, 17, 1356
21. Errey, J. C.; Mukhopadhyay, B.; Kartha, K. P. R; Field, R. A. Chem. Commun. 2004, 2706
22. Peltier, P.; Guégan, J.-P.; Daniellou, R.; Nugier-Chauvin, C.; Ferrières, V. Eur. J. Org. Chem. 2008, 2008, 5988
23. Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752
24. Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661
25. Sanders, W. J.; Kiessling, L. L. Tetrahedron Lett. 1994, 35, 7335
26. Kumar, V.; Gauniyal, H. M.; Shaw, A. K. Tetrahedron: Asymmetry 2007, 18, 2069
27. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470
28. Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307
29. de Lederkremer, R. M.; Nahmad, V. B.; Varela, O. J. Org. Chem. 1994, 59, 690
30. Marlow, A. L.; Kiessling, L. L. Org. Lett. 2001, 3, 2517
31. Mohamady, S.; Desoky, A.; Taylor, S. D. Org. Lett. 2011, 14, 402
32. May, J. F.; Splain, R. A.; Brotschi, C.; Kiessling, L. L. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 11851
33. Levengood, M. R.; Splain, R. A.; Kiessling, L. L. J. Am. Chem. Soc. 2011, 133, 12758
34. Young, D. B.; Duncan, K. Annu. Rev. Microbiol. 1995, 49, 641
35. Pan, F.; Jackson, M.; Ma, Y.; McNeil, M. J. Bacteriol. 2001, 183, 3991
36. Dykhuizen, E. C.; May, J. F.; Tongpenyai, A.; Kiessling, L. L. J. Am. Chem. Soc. 2008, 130, 6706
37. Sanger, F.; Nicklen, S.; Coulson, A. R. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 5463
38. Poulin, M. B.; Zhou, R.; Lowary, T. L. Org. Biomol. Chem. 2012, 10.1039/C2OB25159K
39. Kiessling, L. L.; Splain, R. A. Annu. Rev. Biochem. 2010, 79, 619