Species differences in alternative substrate utilization by the antibacterial target undecaprenyl pyrophosphate synthase

Biochemistry

Volumn 53, Issue 30, 2014, Pages 5042-5050

  Dodbele, Samantha ^a   Martinez, Christina D ^a   Troutman, Jerry M ^a,b  

^a UNIVERSITY OF NORTH CAROLINA AT CHARLOTTE   (United States)

^b University of North Carolina at Charlotte   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASSAYS; BIOCHEMISTRY; BIOSYNTHESIS; CHAINS; ESCHERICHIA COLI; FLUORESCENCE; MAMMALS; SUBSTRATES;

ALTERNATIVE SUBSTRATES; BACTEROIDES FRAGILIS; CHAIN ELONGATION; MULTIPLE SPECIES; SUBSTRATE SELECTIVITY; SUBSTRATE UTILIZATION; UNDECAPRENYL PYROPHOSPHATE SYNTHASE; VIBRIO VULNIFICUS;

BACTERIA;

ALKYL AND ARYL TRANSFERASES; ANTI-BACTERIAL AGENTS; BACTEROIDES FRAGILIS; DRUG DELIVERY SYSTEMS; ESCHERICHIA COLI; HUMANS; MOLECULAR PROBES; SPECIES SPECIFICITY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SUBSTRATE SPECIFICITY; VIBRIO VULNIFICUS;

EID: 84905676250     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi500545g     Document Type: Article

References (31)

1. Huang, S. H., Wu, W. S., Huang, L. Y., Huang, W. F., Fu, W. C., Chen, P. T., Fang, J. M., Cheng, W. C., Cheng, T. J., and Wong, C. H. (2013) New continuous fluorometric assay for bacterial transglycosylase using Forster resonance energy transfer J. Am. Chem. Soc. 135, 17078-17089
2. Faridmoayer, A., Fentabil, M. A., Haurat, M. F., Yi, W., Woodward, R., Wang, P. G., and Feldman, M. F. (2008) Extreme Substrate Promiscuity of the Neisseria Oligosaccharyl Transferase Involved in Protein O-Glycosylation J. Biol. Chem. 283, 34596-34604
3. Perlstein, D. L., Zhang, Y., Wang, T. S., Kahne, D. E., and Walker, S. (2007) The direction of glycan chain elongation by peptidoglycan glycosyltransferases J. Am. Chem. Soc. 129, 12674-12675
4. Chen, M. M., Weerapana, E., Ciepichal, E., Stupak, J., Reid, C. W., Swiezewska, E., and Imperiali, B. (2007) Polyisoprenol specificity in the Campylobacter jejuni N-linked glycosylation pathway Biochemistry 46, 14342-14348
5. James, D. B., Gupta, K., Hauser, J. R., and Yother, J. (2013) Biochemical activities of Streptococcus pneumoniae serotype 2 capsular glycosyltransferases and significance of suppressor mutations affecting the initiating glycosyltransferase Cps2E J. Bacteriol. 195, 5469-5478
6. Mostafavi, A. Z. and Troutman, J. M. (2013) Biosynthetic assembly of the Bacteroides fragilis capsular polysaccharide A precursor bactoprenyl diphosphate-linked acetamido-4-amino-6-deoxygalactopyranose Biochemistry 52, 1939-1949
7. Chang, S. Y., Ko, T. P., Chen, A. P. C., Wang, A. H. J., and Liang, P. H. (2004) Substrate binding mode and reaction mechanism of undecaprenyl pyrophosphate synthase deduced from crystallographic studies Protein Sci. 13, 971-978
8. Chang, S. Y., Ko, T. P., Liang, P. H., and Wang, A. H. J. (2003) Catalytic mechanism revealed by the crystal structure of undecaprenyl pyrophosphate synthase in complex with sulfate, magnesium, and triton J. Biol. Chem. 278, 29298-29307
9. Zhu, W., Zhang, Y., Sinko, W., Hensler, M. E., Olson, J., Molohon, K. J., Lindert, S., Cao, R., Li, K., Wang, K., Wang, Y., Liu, Y. L., Sankovsky, A., de Oliveira, C. A., Mitchell, D. A., Nizet, V., McCammon, J. A., and Oldfield, E. (2013) Antibacterial drug leads targeting isoprenoid biosynthesis Proc. Natl. Acad. Sci. U.S.A. 110, 123-128
10. Guo, R. T., Cao, R., Liang, P. H., Ko, T. P., Chang, T. H., Hudock, M. P., Jeng, W. Y., Chen, C. K. M., Zhang, Y. H., Song, Y. C., Kuo, C. J., Yin, F. L., Oldfield, E., and Wang, A. H. J. (2007) Bisphosphonates target multiple sites in both cis- and trans-prenyltransferases Proc. Natl. Acad. Sci. U.S.A. 104, 10022-10027
11. Durrant, J. D., Cao, R., Gorfe, A. A., Zhu, W., Li, J., Sankovsky, A., Oldfield, E., and McCammon, J. A. (2011) Non-bisphosphonate inhibitors of isoprenoid biosynthesis identified via computer-aided drug design Chem. Biol. Drug Des. 78, 323-332
12. Peukert, S., Sun, Y., Zhang, R., Hurley, B., Sabio, M., Shen, X., Gray, C., Dzink-Fox, J., Tao, J., Cebula, R., and Wattanasin, S. (2008) Design and structure-activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): Tetramic, tetronic acids and dihydropyridin-2-ones Bioorg. Med. Chem. Lett. 18, 1840-1844
13. Kuo, C. J., Guo, R. T., Lu, I. L., Liu, H. G., Wu, S. Y., Ko, T. P., Wang, A. H. J., and Liang, P. H. (2008) Structure-based inhibitors exhibit differential activities against Helicobacter pylori and Escherichia coli undecaprenyl pyrophosphate synthases J. Biomed. Biotechnol. DOI: 10.1155/2008/841312
14. Chang, S. Y., Chen, Y. K., Wang, A. H., and Liang, P. H. (2003) Identification of the active conformation and the importance of length of the flexible loop 72-83 in regulating the conformational change of undecaprenyl pyrophosphate synthase Biochemistry 42, 14452-14459
15. Guo, R. T., Ko, T. P., Chen, A. P., Kuo, C. J., Wang, A. H., and Liang, P. H. (2005) Crystal structures of undecaprenyl pyrophosphate synthase in complex with magnesium, isopentenyl pyrophosphate, and farnesyl thiopyrophosphate: Roles of the metal ion and conserved residues in catalysis J. Biol. Chem. 280, 20762-20774
16. Teng, K. H. and Liang, P. H. (2012) Structures, mechanisms and inhibitors of undecaprenyl diphosphate synthase: A cis-prenyltransferase for bacterial peptidoglycan biosynthesis Bioorg. Chem. 43, 51-57
17. Pan, J. J., Chiou, S. T., and Liang, P. H. (2000) Product distribution and pre-steady-state kinetic analysis of Escherichia coli undecaprenyl pyrophosphate synthase reaction Biochemistry 39, 10936-10942
18. Pan, J. J., Ramamoorthy, G., and Poulter, C. D. (2013) Dependence of the Product Chain-Length on Detergents for Long-Chain E-Polyprenyl Diphosphate Synthases Biochemistry 52, 5002-5008
19. Li, H., Huang, J. Z., Jiang, X. H., Seefeld, M., McQueney, M., and Macarron, R. (2003) The effect of triton concentration on the activity of undecaprenyl pyrophosphate synthase inhibitors J. Biomol. Screening 8, 712-715
20. Teng, K. H., Chen, A. P. C., Kuo, C. J., Li, Y. C., Liu, H. G., Chen, C. T., and Liang, P. H. (2011) Fluorescent substrate analog for monitoring chain elongation by undecaprenyl pyrophosphate synthase in real time Anal. Biochem. 417, 136-141
21. Chen, A. P. C., Chen, Y. H., Liu, H. P., Li, Y. C., Chen, C. T., and Liang, P. H. (2002) Synthesis and application of a fluorescent substrate analogue to study ligand interactions for undecaprenyl pyrophosphate synthase J. Am. Chem. Soc. 124, 15217-15224
22. Lujan, D. K., Stanziale, J. A., Mostafavi, A. Z., Sharma, S., and Troutman, J. M. (2012) Chemoenzymatic synthesis of an isoprenoid phosphate tool for the analysis of complex bacterial oligosaccharide biosynthesis Carbohydr. Res. 359, 44-53
23. Mostafavi, A. Z., Lujan, D. K., Erickson, K. M., Martinez, C. D., and Troutman, J. M. (2013) Fluorescent probes for investigation of isoprenoid configuration and size discrimination by bactoprenol-utilizing enzymes Bioorg. Med. Chem. 21, 5428-5435
24. Fujikura, K., Maki, Y., Ohya, N., Satoh, M., and Koyama, T. (2008) Kinetic studies of Micrococcus luteus B-P 26 undecaprenyl diphosphate synthase reaction using 3-desmethyl allylic substrate analogs Biosci., Biotechnol., Biochem. 72, 851-855
25. Davisson, V. J., Woodside, A. B., Neal, T. R., Stremler, K. E., Muehlbacher, M., and Poulter, C. D. (1986) Phosphorylation of Isoprenoid Alcohols J. Org. Chem. 51, 4768-4779
26. Chehade, K. A., Andres, D. A., Morimoto, H., and Spielmann, H. P. (2000) Design and synthesis of a transferable farnesyl pyrophosphate analogue to Ras by protein farnesyltransferase J. Org. Chem. 65, 3027-3033
27. Guo, R. T., Ko, T. P., Chen, A. P. C., Kuo, C. J., Wang, A. H. J., and Liang, P. H. (2005) Crystal structures of undecaprenyl pyrophosphate synthase in complex with magnesium, isopentenyl pyrophosphate, and farnesyl thiopyrophosphate: Roles of the metal ion and conserved residues in catalysis J. Biol. Chem. 280, 20762-20774
28. Troutman, J. M., Sharma, S., Erickson, K. M., and Martinez, C. D. (2014) Functional identification of a galactosyltransferase critical to Bacteroides fragilis capsular polysaccharide A biosynthesis Carbohydr. Res. 395, 19-28
29. Chehade, K. A. H., Kiegiel, K., Isaacs, R. J., Pickett, J. S., Bowers, K. E., Fierke, C. A., Andres, D. A., and Spielmann, H. P. (2002) Photoaffinity analogues of farnesyl pyrophosphate transferable by protein farnesyl transferase J. Am. Chem. Soc. 124, 8206-8219
30. Labadie, G. R., Viswanathan, R., and Poulter, C. D. (2007) Farnesyl diphosphate analogues with omega-bioorthogonal azide and alkyne functional groups for protein farnesyl transferase-catalyzed ligation reactions J. Org. Chem. 72, 9291-9297
31. Crunkhorn, S. (2013) New antibiotics on the horizon? Nat. Rev. Drug Discovery 12, 99-99