Crystal structure of BRL 42715, C6-(N1-methyl-1,2,3-triazolylmethylene)penem, in complex with Enterobacter cloacae 908R beta-lactamase: evidence for a stereoselective mechanism from docking studies.
[en] BRL 42715, C6-(N1-methyl-1,2,3-triazolylmethylene)penem, is an active-site-directed inactivator of bacterial beta-lactamases. The crystal structure of Enterobacter cloacae 908R class C beta-lactamase in complex with BRL 42715, docking, and energy minimization studies explain stereoselectivity of the binding of C6-(heterocyclic methylene)penems against class C beta-lactamase.
Disciplines :
Biochemistry, biophysics & molecular biology
Author, co-author :
Michaux, Catherine
Charlier, Paulette ; Université de Liège - ULiège > Département des sciences de la vie > Cristallographie des macromolécules biologiques
Frère, Jean-Marie ; Université de Liège - ULiège > Centre d'ingénierie des protéines
Wouters, Johan
Language :
English
Title :
Crystal structure of BRL 42715, C6-(N1-methyl-1,2,3-triazolylmethylene)penem, in complex with Enterobacter cloacae 908R beta-lactamase: evidence for a stereoselective mechanism from docking studies.
Publication date :
2005
Journal title :
Journal of the American Chemical Society
ISSN :
0002-7863
eISSN :
1520-5126
Publisher :
American Chemical Society, Washington, United States - District of Columbia
scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.
Bibliography
Matagne, A.; Dubus, A.; Galleni, M.; Frere, J. M. Nat. Prod. Rep. 1999, 16, 1-19.
Frere, J. M. Mol. Microbiol. 1995, 16, 385-395.
Lee, N.; Yuen, K. Y.; Kumana, C. R. Drugs 2003, 63, 1511-1524.
Osborne, N. F.; Broom, N. J. P.; Coulton, S.; Harbridge, J. B.; Harris, M. A.; Stirling-Francois, I.; Walker, G. J. Chem. Soc., Chem. Commun. 1989, 371-372.
Galleni, M.; Franceschini, N.; Quinting, B.; Fattorini, L.; Orefici, G.; Oratore, A.; Frere, J. M.; Amicosante, G. Antimicrob. Agents Chemother. 1994, 38, 1608-1614.
Coleman, K.; Griffin, D. R. J.; Page, J. W. J.; Upshon, P. A. Antimicrob. Agents Chemother. 1989, 33, 1580-1587.
Qadri, S. M.; Ueno, Y.; Burdette, M.; Kroschinsky, R.; Almodovar, E. Chemotherapy 1991, 37, 398-404.
Jackson, D. Pharmacothempy 1991, 11, 37S-39S.
Muratani, T.; Yokota, E.; Nakane, T.; Inoue, E.; Mitsuhashi, S. J. Antimicrob. Chemother. 1993, 32, 421-429.
Zhou, X. Y.; Kitzis, M. D.; Acar, J. F.; Gutmann, L. J. Antimicrob. Chemother. 1993, 31, 473-480.
Coleman, K.; Griffin, D. R.; Upshon, P. A. Antimicrob. Agents Chemother. 1991, 35, 1748-1752.
Broom, N. J. P.; Farmer, T. H.; Osborne, N. F.; Tyler, J. W. J. Chem. Soc., Chem. Commun. 1992, 22, 1663-1664.
Nukaga, M.; Abe, T.; Venkatesan, A. M.; Mansour, T. S.; Bonomo, R. A.; Knox, J. R. Biochemistry 2003, 42, 13152-13159.
Nukaga, M.; Kumar, S.; Nukaga, K.; Pratt, R. F.; Knox, J. R. J. Biol. Chem. 2004, 279, 9344-9352. Epub 2003, Dec, 9343.
Bulychev, A.; Massova, I.; Lerner, S. A.; Mobashery, S. J. Am. Chem. Soc. 1995, 117, 4797-4801.
Crichlow, G. V.; Kuzin, A. P.; Nukaga, M.; Mayama, K.; Sawai, T.; Knox, J. R. Biochemistry 1999, 38, 10256-10261.
Crichlow, G. V.; Nukaga, M.; Doppalapudi, V. R.; Buynak, J. D.; Knox, J. R. Biochemistry 2001, 40, 6233-6239.
Details are given as Supporting Information.
Venkatesan, A. M.; Gu, Y.; Dos Santos, O.; Abe, T.; Agarwal, A.; Yang, Y.; Petersen, P. J.; Weiss, W. J.; Mansour, T. S.; Nukaga, M.; Hujer, A. M.; Bonomo, R. A.; Knox, J. R. J. Med. Chem. 2004, 47, 6556-6568.
This website uses cookies to improve user experience. Read more
Save & Close
Accept all
Decline all
Show detailsHide details
Cookie declaration
About cookies
Strictly necessary
Performance
Strictly necessary cookies allow core website functionality such as user login and account management. The website cannot be used properly without strictly necessary cookies.
This cookie is used by Cookie-Script.com service to remember visitor cookie consent preferences. It is necessary for Cookie-Script.com cookie banner to work properly.
Performance cookies are used to see how visitors use the website, eg. analytics cookies. Those cookies cannot be used to directly identify a certain visitor.
Used to store the attribution information, the referrer initially used to visit the website
Cookies are small text files that are placed on your computer by websites that you visit. Websites use cookies to help users navigate efficiently and perform certain functions. Cookies that are required for the website to operate properly are allowed to be set without your permission. All other cookies need to be approved before they can be set in the browser.
You can change your consent to cookie usage at any time on our Privacy Policy page.
