Design and characterization of mechanism-based inhibitors for the tyrosine aminomutase SgTAM

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 10, 2008, Pages 3099-3102

  Montavon, Timothy J ^a   Christianson, Carl V ^a   Festin, Grace M ^a   Shen, Ben ^b   Bruner, Steven D ^a  

^a BOSTON COLLEGE   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Amino acid; 4 Methylideneimidazole 5 one; Aminomutase; Ammonia lyase; Enediyne; MIO; Natural product biosynthesis; Nonribosomal peptide

Indexed keywords

4 METHYLIDENEIMIDAZOL 5 ONE; ENZYME INHIBITOR; IMIDAZOLE DERIVATIVE; MUTASE; SGTAM PROTEIN; TYROSINE AMINOMUTASE INHIBITOR;

ARTICLE; CHEMICAL INTERACTION; COVALENT BOND; DRUG DESIGN; DRUG SYNTHESIS; ENZYME SUBSTRATE; REACTION ANALYSIS; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; ENZYME INHIBITORS; EPOXY COMPOUNDS; IMIDAZOLES; INTRAMOLECULAR TRANSFERASES; MOLECULAR STRUCTURE;

EID: 43549087598     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.11.046     Document Type: Article

References (22)

1. For examples see:. Van Lanen S.G., Oh T.J., Liu W., Wendt-Pienkowski E., and Shen B. J. Am. Chem. Soc. 129 (2007) 13082
2. Fortin P.D., Walsh C.T., and Magarvey N.A. Nature 448 (2007) 824
3. Rachid S., Krug D., Weissman K.J., and Muller R. J. Biol. Chem. 282 (2007) 21810
4. Deng J.Z., Newman D.J., and Hecht S.M. J. Nat. Prod. 68 (2005) 465
5. Walker K.D., Klettke K., Akiyama T., and Croteau R. J. Biol. Chem. 279 (2004) 53947
6. Poppe L., and Retey J. Angew. Chem. Int. Ed. Engl. 44 (2005) 3668
7. Baedeker M., and Schulz G.E. Structure 10 (2002) 61
8. Christenson S.D., Liu W., Toney M.D., and Shen B. J. Am. Chem. Soc. 125 (2003) 6062
9. Christenson S.D., Wu W., Spies M.A., Shen B., and Toney M.D. Biochemistry 42 (2003) 12708
10. Walker K.D., Klettke K., Akiyama T., and Croteau R. J. Biol. Chem. 279 (2004) 53947
11. Christianson C.V., Montavon T.J., Van Lanen S.G., Shen B., and Bruner S.D. Biochemistry 46 (2007) 7205
12. For recent examples see:. Klettke K.L., Sanyal S., Mutatu W., and Walker K.D. J. Am. Chem. Soc. 129 (2007) 6988
13. Kennedy D.R., Ju J., Shen B., and Beerman T.A. Proc. Natl. Acad. Sci. U.S.A 104 (2007) 17632
14. Christianson, C. V.; Montavon, T. J.; Festin, G. M.; Cooke, H. A.; Shen, B.; Bruner, S. D. J. Am. Chem. Soc., in press.
15. Wu X.Y., She X., and Shi Y. J. Am. Chem. Soc. 124 (2002) 8792
16. Experimental procedures and complete characterization of all novel compounds are included in the supplemental section accompanying this letter.
17. Staas D.D., Savage K.L., Homnick C.F., Tsou N.N., and Ball R.G. J. Org. Chem. 67 (2002) 8276
18. Sorochinsky A., Voloshin N., Markovsky A., Belik M., Yasuda N., Uekusa H., Ono T., Berbasov D.O., and Soloshonok V.A. J. Org. Chem. 68 (2003) 7448
19. Liu G., Cogan D.A., and Ellman J.A. J. Am. Chem. Soc. 119 (1997) 9913
20. Louie G.V., Bowman M.E., Moffitt M.C., Baiga T.J., Moore B.S., and Noel J.P. Chem. Biol. 13 (2006) 1327
21. Watts K.T., Mijts B.N., Lee P.C., Manning A.J., and Schmidt-Dannert C. Chem. Biol. 13 (2006) 1317
22. Refer to the supplemental section for assay conditions.