Total synthesis of n-acetylglucosamine-1,6-anhydro-n- acetylmuramylpentapeptide and evaluation of its turnover by ampd from escherichia coli

Journal of the American Chemical Society

Volumn 131, Issue 14, 2009, Pages 5187-5193

  Hesek, Dusan ^a   Lee, Mijoon ^a   Zhang, Weilie ^a   Noll, Bruce C ^a   Mobashery, Shahriar ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL CELLS; CELL WALLS; GLUCOSAMINE; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIUM; INFLAMMATORY RESPONSE; N-ACETYLGLUCOSAMINE; PEPTIDOGLYCAN; RECYCLING PROCESS; TOTAL SYNTHESIS;

AMINES; BACTERIA; BACTERIOLOGY; ENZYMES; ESCHERICHIA COLI; GROWTH KINETICS; POLYSACCHARIDES; RECYCLING; SYNTHESIS (CHEMICAL);

CELL MEMBRANES;

ESCHERICHIA COLI PROTEIN; GLYCOSYLTRANSFERASE; AMPD PROTEIN, BACTERIA; BACTERIAL PROTEIN; N ACETYLGLUCOSAMINE; N ACETYLMURAMOYLALANINE AMIDASE; OLIGOPEPTIDE;

ARTICLE; BACTERIAL CELL WALL; ENZYME ACTIVITY; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HYDROLYSIS; IMMUNE RESPONSE; NONHUMAN; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; RECYCLING; ANALOGS AND DERIVATIVES; CELL WALL; ENZYME SPECIFICITY; ENZYMOLOGY; GLYCOSYLATION; KINETICS; METABOLISM; SYNTHESIS;

ACETYLGLUCOSAMINE; BACTERIAL PROTEINS; CELL WALL; ESCHERICHIA COLI; GLYCOSYLATION; HYDROLYSIS; KINETICS; N-ACETYLMURAMOYL-L-ALANINE AMIDASE; OLIGOPEPTIDES; SUBSTRATE SPECIFICITY;

EID: 67749113466     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja808498m     Document Type: Article

References (58)

1. Coyette, J.; van der Ende, A. FEMS Microbiol. Rev. 2008, 32, 147-148.
2. Höltje, J.-V. Cell Walls, Bacterial. In Desk Encyclopedia of Microbiology; Schaechter, M., Ed.; Elsevier Academic Press: San Diego, London, 2004; pp 239-250.
3. Suvorov, M.; Fisher, J. F.; Mobashery, S. Bacterial Cell Wall: Morphology and Biochemistry. In Practical Handbook of Microbiology, 2nd ed.; Goldman, E., Green, L. H., Eds.; CRC Press:Boca Raton, FL, 2008; pp 153-183.
4. Silver, L. L. Biochem. Pharmacol. 2006, 71, 996-1005.
5. Van Bambeke, F.; Mingeot-Leclercq, M. P.; Struelens, M. J.; Tulkens, P. M. Trends Pharmacol. Sci. 2008, 29, 124-134.
6. Vollmer, W.; Höltje, J.-V. J. Bacteriol. 2004, 186, 5978-5987.
7. de Pedro, M. A.; Donachie, W. D.; Höltje, J.-V.; Schwarz, H. J. Bacteriol. 2001, 183, 4115-4126.
8. Park, J. T.; Uehara, T. Microbiol. Mol. Biol. Rev. 2008, 72, 211-227.
9. Wiedemann, B.; Pfeifle, D.; Wiegand, I.; Janas, E. Drug Resist. Updates 1998, 1, 223-226.
10. Jacobs, C.; Frere, J. M.; Normark, S. Cell 1997, 88, 823-832.
11. Scheurwater, E.; Reid, C. W.; Clarke, A. J. Int. J. Biochem. Cell Biol. 2008, 40, 586-591.
12. Scheurwater, E. M.; Clarke, A. J. J. Biol. Chem. 2008, 283, 8363-8373.
13. Suvorov, M.; Lee, M.; Hesek, D.; Boggess, B.; Mobashery, S. J. Am. Chem. Soc. 2008, 130, 11878-11879.
14. Taylor, A.; Das, B. C.; Vanheijenoort, J. Eur. J. Biochem. 1975, 53, 47-54.
15. Cheng, Q. M.; Park, J. T. J. Bacteriol. 2002, 184, 6434-6436.
16. Chang, C. I.; Chelliah, Y.; Borek, D.; Mengin-Lecreulx, D.; Deisenhofer, J. Science 2006, 311, 1761-1764.
17. Cloud-Hansen, K. A.; Peterson, S. B.; Stabb, E. V.; Goldman, W. E.; McFall-Ngai, M. J.; Handelsman, J. Nat. Rev. Microbiol. 2006, 4, 710-716.
18. Kohler, P. L.; Cloud, K. A.; Hackett, K. T.; Beck, E. T.; Dillard, J. P. Microbiology 2005, 151, 3081-3088.
19. Traub, S.; Kubasch, N.; Morath, S.; Kresse, M.; Hartung, T.; Schmidt, R. R.; Hermann, C. J. Biol. Chem. 2004, 279, 8694-8700.
20. Krueger, J. M.; Karnovsky, M. L.; Martin, S. A.; Pappenheimer, J. R.; Walter, J.; Biemann, K. J. Biol. Chem. 1984, 259, 12659-12662.
21. Krueger, J. M.; Rosenthal, R. S.; Martin, S. A.; Walter, J.; Davenne, D.; Shoham, S.; Kubillus, S. L.; Biemann, K. Brain Res. 1987, 403, 249-257.
22. Paulsen, H.; Himpkamp, P.; Peters, T. Liebigs Ann. Chem. 1986, 664-674.
23. Watanabe, K.; Tanaka, R.; Sakurai, H.; Iguchi, K.; Yamada, Y.; Hsu, C. S.; Sakuma, C.; Kikuchi, H.; Shibayama, H.; Kawai, T. Chem. Pharm. Bull. 2007, 55, 780-783.
24. Kawasaki, A.; Karasudani, Y.; Otsuka, Y.; Hasegawa, M.; Inohara, N.; Fujimoto, Y.; Fukase, K. Chem. Eur. J. 2008, 14, 10318-10330.
25. Kubasch, N.; Schmidt, R. R. Eur. J. Org. Chem. 2002, 2710-2726.
26. Hesek, D.; Lee, M.; Morio, K.-I.; Mobashery, S. J. Org. Chem. 2004, 69, 2137-2146.
27. Merser, C.; Sinaÿ, P. Tetrahedron Lett. 1973, 14, 1029-1032.
28. Ganguli, A. R. S.; Coward, J. K. Tetrahedron: Asymmetry 2005, 16, 411-424.
29. Krohn, K.; Gehle, D.; Flörke, U. Eur. J. Org. Chem. 2005, 2841-2848.
30. Bartolozzi, A.; Pacciani, S.; Benvenuti, C.; Cacciarini, M.; Liguori, F.; Menichetti, S.; Nativi, C. J. Org. Chem. 2003, 68, 8529-8533.
31. Kinzy, W.; Schmidt, R. R. Tetrahedron Lett. 1987, 28, 1981-1984.
32. Hesek, D.; Lee, M.; Noll, B. C.; Fisher, J. F.; Mobashery, S. J. Org. Chem. 2009, 74, 2567-2570.
33. Banoub, J.; Boullanger, P.; Lafont, D. Chem. Rev. 1992, 92, 1167-1195.
34. Furegati, S.; White, A. J. P.; Miller, A. D. Synlett 2005, 2385-2387.
35. Tsubouchi, A.; Onishi, K.; Takeda, T. J. Am. Chem. Soc. 2006, 128, 14268-14269.
36. Yamazaki, T.; Mizutani, K.; Kitazume, T. J. Org. Chem. 1993, 58, 4346-4359.
37. Yoon, S. J. Korean Chem. Soc. 2002, 46, 590-594.
38. Teranishi, K.; Ueno, F. Tetrahedron Lett. 2003, 44, 4843-4848.
39. Moser, W. H.; Sun, L.; Huffman, J. C. Org. Lett. 2001, 3, 3389-3391.
40. Sole, S.; Gornitzka, H.; Guerret, O.; Bertrand, G. J. Am. Chem. Soc. 1998, 120, 9100-9101.
41. Tailler, D.; Jacquinet, J. C.; Noirot, A. M.; Beau, J. M. J. Chem. Soc., Perkin Trans. 1 1992, 3163-3164.
42. Trnka, T.;Č erny',M. Collect. Czech. Chem. Commun. 1971, 36, 2216-2225.
43. Czernecki, S.; Leteux, C.; Veyrières, A. Tetrahedron Lett. 1992, 33, 221-224.
44. Xue, J.; Guo, Z. W. Tetrahedron Lett. 2001, 42, 6487-6489.
45. Č erny', M.; Paca'k, J.; Staněk, J. Collect. Czech. Chem. Commun. 1965, 30, 1151-1157.
46. Sasaki, M.; Koike, T.; Sakai, R.; Tachibana, K. Tetrahedron Lett. 2000, 41, 3923-3926.
47. Krintel, S. L.; Jime'nez-Barbero, J.; Skrydstrup, T. Tetrahedron Lett. 1999, 40, 7565-7568.
48. Mikkelsen, L. M.; Krintel, S. L.; Jime'nez-Barbero, J.; Skrydstrup, T. J. Org. Chem. 2002, 67, 6297-6308.
49. Paulsen, H.; Koebernick, H.; Stenzel, W.; Koll, P. Tetrahedron Lett. 1975, 1493-1494.
50. Oguri, S.; Ishihara, H.; Tejima, S. Chem. Pharm. Bull. 1980, 28, 35-41.
51. El Ashry, E. S. H.; Aly, M. R. E. Pure Appl. Chem. 2007, 79, 2229-2242.
52. Inamura, S.; Fukase, K.; Kusumoto, S. Tetrahedron Lett. 2001, 42, 7613-7616.
53. Srivastava, V. K. Carbohydr. Res. 1982, 103, 286-292.
54. Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9374-9380.
55. Dullenkopf, W.; Castro-Palomino, J. C.; Manzoni, L.; Schmidt, R. R. Carbohydr. Res. 1996, 296, 135-147.
56. Aly, M. R. E.; Castro-Palomino, J. C.; Ibrahim, E. S. I.; El-Ashry, E. S. H.; Schmidt, R. R. Eur. J. Org. Chem. 1998, 2305-2316.
57. Györgydea'k, Z.; Szila'gyi, L.; Paulsen, H. J. Carbohydr. Chem. 1993, 12, 139-163.
58. Hesek, D.; Suvorov, M.; Morio, K.; Lee, M.; Brown, S.; Vakulenko, S. B.; Mobashery, S. J. Org. Chem. 2004, 69, 778-784.