Separate Entrance and Exit Portals for Ligand Traffic in Mycobacterium tuberculosis FabH

Chemistry and Biology

Volumn 15, Issue 4, 2008, Pages 402-412

  Sachdeva, Sarbjot ^a,b   Musayev, Faik N ^b   Alhamadsheh, Mamoun M ^a   Scarsdale, J Neel ^b   Wright, H Tonie ^b   Reynolds, Kevin A ^a  

^a PORTLAND STATE UNIVERSITY   (United States)

^b VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

CHEMBIO

Indexed keywords

3 OXOACYL ACYL CARRIER PROTEIN SYNTHASE; ACYL COENZYME A; CYSTEINE; ENZYME INHIBITOR; LIGAND; MYCOLIC ACID; SOLVENT;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; ELECTROSPRAY MASS SPECTROMETRY; ENZYME ACTIVE SITE; ENZYMOLOGY; GENETICS; HYDROPHOBICITY; METABOLISM; MUTATION; MYCOBACTERIUM TUBERCULOSIS; PROTEIN BINDING; X RAY CRYSTALLOGRAPHY;

3-OXOACYL-(ACYL-CARRIER-PROTEIN) SYNTHASE; ACYL COENZYME A; BINDING SITES; CATALYTIC DOMAIN; CRYSTALLOGRAPHY, X-RAY; CYSTEINE; ENZYME INHIBITORS; HYDROPHOBICITY; LIGANDS; MODELS, MOLECULAR; MUTATION; MYCOBACTERIUM TUBERCULOSIS; MYCOLIC ACIDS; PROTEIN BINDING; SOLVENTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

BACTERIA (MICROORGANISMS); MYCOBACTERIUM TUBERCULOSIS;

EID: 41949116280     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2008.03.007     Document Type: Article

References (34)

1. Alhamadsheh M.M., Musayev F., Komissarov A.A., Sachdeva S., Wright H.T., Scarsdale J.N., Florova G., and Reynolds K.A. Alkyl-CoA disulfides as inhibitors and mechanistic probes for FabH enzymes. Chem. Biol. 14 (2007) 513-524
2. Asselineau C., Asselineau J., Laneelle G., and Laneelle M.A. The biosynthesis of mycolic acids by mycobacteria: current and alternative hypotheses. Prog. Lipid Res. 41 (2002) 501-523
3. Bhatt A., Molle V., Besra G.S., Jacobs Jr. W.R., and Kremer L. The Mycobacterium tuberculosis FAS-II condensing enzymes: their role in mycolic acid biosynthesis, acid-fastness, pathogenesis and in future drug development. Mol. Microbiol. 64 (2007) 1442-1454
4. Brown A.K., Bhatt A., Singh A., Saparia E., Evans A.F., and Besra G.S. Identification of the dehydratase component of the mycobacterial mycolic acid-synthesizing fatty acid synthase-II complex. Microbiology 153 (2007) 4166-4173
5. Brown A.K., Sridharan S., Kremer L., Lindenberg S., Dover L.G., Sacchettini J.C., and Besra G.S. Probing the mechanism of the Mycobacterium tuberculosis β-ketoacyl-acyl carrier protein synthase III mtFabH: factors influencing catalysis and substrate specificity. J. Biol. Chem. 280 (2005) 32539-32547
6. Brunger A.T., Adams P.D., Clore G.M., DeLano W.L., Gros P., Grosse-Kunstleve R.W., Jiang J.S., Kuszewski J., Nilges M., Pannu N.S., et al. Crystallography & NMR system: a new software suite for macromolecular structure determination. Acta Crystallogr. D Biol. Crystallogr. 54 (1998) 905-921
7. Choi K.H., Heath R.J., and Rock C.O. β-Ketoacyl-acyl carrier protein synthase III (FabH) is a determining factor in branched-chain fatty acid biosynthesis. J. Bacteriol. 182 (2000) 365-370
8. Choi K.H., Kremer L., Besra G.S., and Rock C.O. Identification and substrate specificity of β-ketoacyl (acyl carrier protein) synthase III (mtFabH) from Mycobacterium tuberculosis. J. Biol. Chem. 275 (2000) 28201-28207
9. Cohen-Gonsaud M., Ducasse-Cabanot S., Quemard A., and Labesse G. Ligand-induced fit in mycobacterial MabA: the sequence-specific C-terminus locks the conformational change. Proteins 60 (2005) 392-400
10. Cohen-Gonsaud M., Ducasse S., Hoh F., Zerbib D., Labesse G., and Quemard A. Crystal structure of MabA from Mycobacterium tuberculosis, a reductase involved in long-chain fatty acid biosynthesis. J. Mol. Biol. 320 (2002) 249-261
11. Emsley P., and Cowtan K. Coot: model-building tools for molecular graphics. Acta Crystallogr. D Biol. Crystallogr. 60 (2004) 2126-2132
12. Han L., Lobo S., and Reynolds K.A. Characterization of β-ketoacyl-acyl carrier protein synthase III from Streptomyces glaucescens and its role in initiation of fatty acid biosynthesis. J. Bacteriol. 180 (1998) 4481-4486
13. Jarlier V., and Nikaido H. Mycobacterial cell wall: structure and role in natural resistance to antibiotics. FEMS Microbiol. Lett. 123 (1994) 11-18
14. Jenni S., Leibundgut M., Boehringer D., Frick C., Mikolasek B., and Ban N. Structure of fungal fatty acid synthase and implications for iterative substrate shuttling. Science 316 (2007) 254-261
15. Larsen M.H., Vilcheze C., Kremer L., Besra G.S., Parsons L., Salfinger M., Heifets L., Hazbon M.H., Alland D., Sacchettini J.C., and Jacobs Jr. W.R. Overexpression of InhA, but not KasA, confers resistance to isoniazid and ethionamide in Mycobacterium smegmatis, M. bovis BCG and M. tuberculosis. Mol. Microbiol. 46 (2002) 453-466
16. Lomakin I.B., Xiong Y., and Steitz T.A. The crystal structure of yeast fatty acid synthase, a cellular machine with eight active sites working together. Cell 129 (2007) 319-332
17. Lu Y.J., Zhang Y.M., and Rock C.O. Product diversity and regulation of type II fatty acid synthases. Biochem. Cell Biol. 82 (2004) 145-155
18. Murshudov G.N., Vagin A.A., Lebedev A., Wilson K.S., and Dodson E.J. Efficient anisotropic refinement of macromolecular structures using FFT. Acta Crystallogr. D Biol. Crystallogr. 55 (1999) 247-255
19. Musayev F., Sachdeva S., Scarsdale J.N., Reynolds K.A., and Wright H.T. Crystal structure of a substrate complex of Mycobacterium tuberculosis β-ketoacyl-acyl carrier protein synthase III (FabH) with lauroyl-coenzyme A. J. Mol. Biol. 346 (2005) 1313-1321
20. Navaza J. AMoRe: an automated package for molecular replacement. Acta Crystallogr. A 50 (1994) 157-163
21. Nikaido H., and Jarlier V. Permeability of the mycobacterial cell wall. Res. Microbiol. 142 (1991) 437-443
22. Pflugrath J.W. The finer things in X-ray diffraction data collection. Acta Crystallogr. D Biol. Crystallogr. 55 (1999) 1718-1725
23. Portevin D., De Sousa-D'Auria C., Houssin C., Grimaldi C., Chami M., Daffe M., and Guilhot C. A polyketide synthase catalyzes the last condensation step of mycolic acid biosynthesis in mycobacteria and related organisms. Proc. Natl. Acad. Sci. USA 101 (2004) 314-319
24. Qiu X., Janson C.A., Smith W.W., Head M., Lonsdale J., and Konstantinidis A.K. Refined structures of β-ketoacyl-acyl carrier protein synthase III. J. Mol. Biol. 307 (2001) 341-356
25. Rozwarski D.A., Grant G.A., Barton D.H., Jacobs Jr. W.R., and Sacchettini J.C. Modification of the NADH of the isoniazid target (InhA) from Mycobacterium tuberculosis. Science 279 (1998) 98-102
26. Sacco E., Covarrubias A.S., O'Hare H.M., Carroll P., Eynard N., Jones T.A., Parish T., Daffe M., Backbro K., and Quemard A. The missing piece of the type II fatty acid synthase system from Mycobacterium tuberculosis. Proc. Natl. Acad. Sci. USA 104 (2007) 14628-14633
27. Sacco E., Legendre V., Laval F., Zerbib D., Montrozier H., Eynard N., Guilhot C., Daffée M., and Quéemard A. Rv3389C from Mycobacterium tuberculosis, a member of the (R)-specific hydratase/dehydratase family. Biochim. Biophys. Acta 1774 (2007) 303-311
28. Scarsdale J.N., Kazanina G., He X., Reynolds K.A., and Wright H.T. Crystal structure of the Mycobacterium tuberculosis β-ketoacyl-acyl carrier protein synthase III. J. Biol. Chem. 276 (2001) 20516-20522
29. Schuettelkopf A.J., and van Aalten D.M.F. PRODRG-a tool for high-throughput crystallography of protein-ligand complexes. Acta Crystallogr. D Biol. Crystallogr. 60 (2004) 1355-1363
30. Sridharan S., Wang L., Brown A.K., Dover L.G., Kremer L., Besra G.S., and Sacchettini J.C. X-ray crystal structure of Mycobacterium tuberculosis β-ketoacyl acyl carrier protein synthase II (mtKasB). J. Mol. Biol. 366 (2007) 469-480
31. Takayama K., Wang C., and Besra G.S. Pathway to synthesis and processing of mycolic acids in Mycobacterium tuberculosis. Clin. Microbiol. Rev. 18 (2005) 81-101
32. Veyron-Churlet R., Bigot S., Guerrini O., Verdoux S., Malaga W., Daffe M., and Zerbib D. The biosynthesis of mycolic acids in Mycobacterium tuberculosis relies on multiple specialized elongation complexes interconnected by specific protein-protein interactions. J. Mol. Biol. 353 (2005) 847-858
33. Veyron-Churlet R., Guerrini O., Mourey L., Daffe M., and Zerbib D. Protein-protein interactions within the fatty acid synthase-II system of Mycobacterium tuberculosis are essential for mycobacterial viability. Mol. Microbiol. 54 (2004) 1161-1172
34. Wong H.C., Liu G., Zhang Y.M., Rock C.O., and Zheng J. The solution structure of acyl carrier protein from Mycobacterium tuberculosis. J. Biol. Chem. 277 (2002) 15874-15880