Synthesis of 4-Diphosphocytidyl-2-C-Methyl-D-Erythritol 2-Phosphate and Kinetic Studies of Mycobacterium tuberculosis IspF

Chemistry and Biology

Volumn 17, Issue 2, 2010, Pages 117-122

  Narayanasamy, Prabagaran ^a   Eoh, Hyungjin ^a   Brennan, Patrick J ^a   Crick, Dean C ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

CHEMBIO; MCIROBIO

Indexed keywords

4 DIPHOSPHOCYTIDYL 2C METHYLERYTHRITOL 2 PHOSPHATE; 4-DIPHOSPHOCYTIDYL-2C METHYLERYTHRITOL 2-PHOSPHATE; BACTERIAL PROTEIN; DRUG DERIVATIVE; ERYTHRITOL; LYASE; RECOMBINANT PROTEIN; SUGAR PHOSPHATE;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; ENZYMOLOGY; GENETICS; KINETICS; METABOLISM; MOLECULAR GENETICS; MYCOBACTERIUM TUBERCULOSIS; SEQUENCE HOMOLOGY; STEREOISOMERISM; SYNTHESIS;

AMINO ACID SEQUENCE; BACTERIAL PROTEINS; ERYTHRITOL; KINETICS; MOLECULAR SEQUENCE DATA; MYCOBACTERIUM TUBERCULOSIS; PHOSPHORUS-OXYGEN LYASES; RECOMBINANT PROTEINS; SEQUENCE HOMOLOGY, AMINO ACID; STEREOISOMERISM; SUGAR PHOSPHATES;

BACTERIA (MICROORGANISMS); MYCOBACTERIUM TUBERCULOSIS;

EID: 77049099840     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2010.01.013     Document Type: Article

References (31)

1. Bailey A.M., Mahapatra S., Brennan P.J., and Crick D.C. Identification, cloning, purification, and enzymatic characterization of Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate synthase. Glycobiology 12 (2002) 813-820
2. Brennan P.J., and Crick D.C. The cell-wall core of Mycobacterium tuberculosis in the context of drug discovery. Curr. Top. Med. Chem. 7 (2007) 475-488
3. Buetow L., Brown A.C., Parish T., and Hunter W.N. The structure of Mycobacteria 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase, an essential enzyme, provides a platform for drug discovery. BMC Struct. Biol. 7 (2007) 68
4. Buhaescu I., and Izzedine H. Mevalonate pathway: a review of clinical and therapeutical implications. Clin. Biochem. 40 (2007) 575-584
5. Campbell T.L., and Brown E.D. Characterization of the depletion of 2-C-methyl-D-erythritol-2,4-cyclodiphosphate synthase in Escherichia coli and Bacillus subtilis. J. Bacteriol. 184 (2002) 5609-5618
6. Dhiman R.K., Schaeffer M.L., Bailey A.M., Testa C.A., Scherman H., and Crick D.C. 1-Deoxy-D-xylulose 5-phosphate reductoisomerase (IspC) from Mycobacterium tuberculosis: towards understanding mycobacterial resistance to fosmidomycin. J. Bacteriol. 187 (2005) 8395-8402
7. Edwards P.A., and Ericsson J. Sterols and isoprenoids: signaling molecules derived from the cholesterol biosynthetic pathway. Annu. Rev. Biochem. 68 (1999) 157-185
8. Eoh H., Brown A.C., Buetow L., Hunter W.N., Parish T., Kaur D., Brennan P.J., and Crick D.C. Characterization of the Mycobacterium tuberculosis 4-diphosphocytidyl-2-C-methyl-D-erythritol synthase: Potential for drug development. J. Bacteriol. 189 (2007) 8922-8927
9. Eoh H., Brennan P.J., and Crick D.C. The Mycobacterium tuberculosis MEP (2C-methyl-D-erythritol 4-phosphate) pathway as a new drug target. Tuberculosis (Edinb) 89 (2008) 1-11
10. Ershov Y.V. 2-C-methylerythritol phosphate pathway of isoprenoid biosynthesis as a target in identifying new antibiotics, herbicides, and immunomodulators: a review [in Russian]. Prikl. Biokhim. Mikrobiol. 43 (2007) 133-147
11. Fellermeier M., Raschke M., Sagner S., Wungsintaweekul J., Schuhr C.A., Hecht S., Kis K., Radykewicz T., Adam P., Rohdich F., et al. Studies on the nonmevalonate pathway of terpene biosynthesis: the role of 2C-methyl-D-erythritol 2,4-cyclodiphosphate in plants. Eur. J. Biochem. 268 (2001) 6302-6310
12. Giessmann D., Heidler P., Haemers T., Van Calenbergh S., Reichenberg A., Jomaa H., Weidemeyerd C., Sanderbrand S., Wiesner J., and Link A. Towards new antimalarial drugs: synthesis of non-hydrolyzable phosphate mimics as feed for a predictive QSAR study on 1-deoxy-D-xylulose-5-phosphate reductoisomerase inhibitors. Chem. Biodivers. 5 (2008) 643-656
13. Herz S., Wungsintaweekul J., Schuhr C.A., Hecht S., Luttgen H., Sagner S., Fellermeier M., Eisenreich W., Zenk M.H., Bacher A., and Rohdich F. Biosynthesis of terpenoids: YgbB protein converts 4-diphosphocytidyl-2C-methyl-D-erythritol 2-phosphate to 2C-methyl-D-erythritol 2,4-cyclodiphosphate. Proc. Natl. Acad. Sci. USA 97 (2000) 2486-2490
14. Illarionova V., Kaiser J., Ostrozhenkova E., Bacher A., Fischer M., Eisenreich W., and Rohdich F. Nonmevalonate terpene biosynthesis enzymes as antiinfective drug targets: substrate synthesis and high-throughput screening methods. J. Org. Chem. 71 (2006) 8824-8834
15. Lehmann C., Lim K., Toedt J., Krajewski W., Howard A., Eisenstein E., and Herzberg O. Structure of 2C-methyl-D-erythrol-2,4-cyclodiphosphate synthase from Haemophilus influenzae: activation by conformational transition. Proteins 49 (2002) 135-138
16. Luttgen H., Rohdich F., Herz S., Wungsintaweekul J., Hecht S., Schuhr C.A., Fellermeier M., Sagner S., Zenk M.H., Bacher A., and Eisenreich W. Biosynthesis of terpenoids: YchB protein of Escherichia coli phosphorylates the 2-hydroxy group of 4-diphosphocytidyl-2C-methyl-D-erythritol. Proc. Natl. Acad. Sci. USA 97 (2000) 1062-1067
17. Narayanasamy P., and Crick D.C. Enantiomeric synthesis of 2-C-methyl-D-erythritol 2,4-cyclodiphosphate. Heterocycles 76 (2008) 243-247
18. Narayanasamy P., Eoh H., and Crick D.C. Chemoenzymatic synthesis of 4-diphosphocytidyl-2-C-methyl-D-erythritol: a substrate for IspE. Tetrahedron Lett. 49 (2008) 4461-4463
19. Ramsden N.L., Buetow L., Dawson A., Kemp L.A., Ulaganathan V., Brenk R., Klebe G., and Hunter W.N. A structure-based approach to ligand discovery for 2C-methyl-d-erythritol-2,4-cyclodiphosphate synthase: a target for antimicrobial therapy. J. Med. Chem. 52 (2009) 2531-2542
20. Richard S.B., Ferrer J.L., Bowman M.E., Lillo A.M., Tetzlaff C.N., Cane D.E., and Noel J.P. Structure and mechanism of 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase: an enzyme in the mevalonate-independent isoprenoid biosynthetic pathway. J. Biol. Chem. 277 (2002) 8667-8672
21. Rohdich F., Eisenreich W., Wungsintaweekul J., Hecht S., Schuhr C.A., and Bacher A. Biosynthesis of terpenoids: 2C-methyl-D-erythritol 2,4-cyclodiphosphate synthase (IspF) from Plasmodium falciparum. Eur. J. Biochem. 268 (2001) 3190-3197
22. Rohmer M. The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants. Nat. Prod. Rep. 16 (1999) 565-574
23. Rohmer M. Diversity in isoprene unit biosynthesis: the methylerythritol phosphate pathway in bacteria and plastids. Pure Appl. Chem. 79 (2007) 739-751
24. Sgraja T., Alphey M.S., Ghilagaber S., Marquez R., Robertson M.N., Hemmings J.L., Lauw S., Rohdich F., Bacher A., Eisenreich W., et al. Characterization of Aquifex aeolicus 4-diphosphocytidyl-2C-methyl-D-erythritol kinase: ligand recognition in a template for antimicrobial drug discovery. FEBS J. 275 (2008) 2779-2794
25. Skorupinska-Tudek K., Poznanski J., Wojcik J., Bienkowski T., Szostkiewicz I., Zelman-Femiak M., Bajda A., Chojnacki T., Olszowska O., Grunler J., et al. Contribution of the mevalonate and methylerythritol phosphate pathways to the biosynthesis of dolichols in plants. J. Biol. Chem. 283 (2008) 21024-21035
26. Steinbacher S., Kaiser J., Wungsintaweekul J., Hecht S., Eisenreich W., Gerhardt S., Bacher A., and Rohdich F. Structure of 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase involved in mevalonate-independent biosynthesis of isoprenoids. J. Mol. Biol. 316 (2002) 79-88
27. Testa C.A., Lherbet C., Pojer F., Noel J.P., and Poulter C.D. Cloning and expression of IspDF from Mesorhizobium loti: characterization of a bifunctional protein that catalyzes non-consecutive steps in the methylerythritol phosphate pathway. Biochim. Biophys. Acta. 1764 (2006) 85-96
28. Urbansky M., Davis C.E., Surjan J.D., and Coates R.M. Synthesis of enantiopure 2-C-methyl-D-erythritol 4-phosphate and 2,4-cyclodiphosphate from D-arabitol. Org. Lett. 6 (2004) 135-138
29. World Health Organization. Global tuberculosis control: surveillance, planning, and financing (WHO/HTM/TB/2007.376) (2007), World Health Organization, Geneva
30. Zhao M., Li X., Xu P., Shen X., Gui X.H., Wang L.L., DeRiemer K., Mei J., and Gao Q. Transmission of MDR and XDR tuberculosis in Shanghai, China. PLoS ONE 4 (2009) e4370
31. Zygmunt J., Kafarski P., and Mastalerz P. Preparation of oxoalkanephosphonic acids. Synthesis-Stuttgart 8 (1978) 609-612