Bacterial transglycosylase inhibitors

Current Opinion in Chemical Biology

Volumn 9, Issue 5, 2005, Pages 459-466

  Ostash, Bohdan ^a   Walker, Suzanne ^a  

^a HARVARD MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MERSACIDIN; NISIN; RAMOPLANIN; TEICOPLANIN; VANCOMYCIN;

ANTIBIOTIC RESISTANCE; CONTROLLED STUDY; GENE TARGETING; GLYCOSYLATION; HIGH THROUGHPUT SCREENING; MOLECULAR GENETICS; NONHUMAN; REVIEW;

ANTI-BACTERIAL AGENTS; BACTERIA; BIOLOGICAL PRODUCTS; CARBOHYDRATE CONFORMATION; ENZYME INHIBITORS; PEPTIDOGLYCAN GLYCOSYLTRANSFERASE;

BACTERIA (MICROORGANISMS);

EID: 25144486056     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbpa.2005.08.014     Document Type: Review

References (60)

1. F.M. Walsh, and S.G. Amyes Microbiology and drug resistance mechanisms of fully resistant pathogens Curr Opin Microbiol 7 2004 439 444
2. C.T. Walsh Antibiotics: Action, Origins, Resistance, edn 1 2003 ASM Press
3. T.D. Bugg Bacterial peptidoglycan biosynthesis and its inhibition B.M. Pinto Comprehensive Natural Products Chemistry, Edn 3 1999 Elsevier 241 294
4. Y. Hu, L. Chen, S. Ha, B. Gross, B. Falcone, D. Walker, M. Mokhtarzadeh, and S. Walker Crystal structure of the MurG:UDP-GlcNAc complex reveals common structural principles of a superfamily of glycosyltransferases Proc Natl Acad Sci USA 100 2003 845 849
5. A. El Zoeiby, F. Sanschagrin, and R.C. Levesque Structure and function of the Mur enzymes: development of novel inhibitors Mol Microbiol 47 2003 1 12
6. C. Morlot, L. Pernot, A. Le Gouellec, A.M. Di Guilmi, T. Vernet, O. Dideberg, and A. Dessen Crystal structure of a peptidoglycan synthesis regulatory factor (PBP3) from Streptococcus pneumoniae J Biol Chem 280 2005 15984 15991
7. P. Macheboeuf, A.M. Di Guilmi, V. Job, T. Vernet, O. Dideberg, and A. Dessen Active site restructuring regulates ligand recognition in class A penicillin-binding proteins Proc Natl Acad Sci USA 102 2005 577 582 This is the first crystal structure of the TP domain of class A PBP. Conformational changes in the protein are suggested to be essential for ligand recognition.
8. J.F. Fisher, S.O. Meroueh, and S. Mobashery Bacterial resistance to β-lactam antibiotics: compelling opportunism, compelling opportunity Chem Rev 105 2005 395 424
9. L. Pernot, L. Chesnel, A. Le Gouellec, J. Croize, T. Vernet, O. Dideberg, and A. Dessen A PBP2x from a clinical isolate of Streptococcus pneumoniae exhibits an alternative mechanism for reduction of susceptibility to beta-lactam antibiotics J Biol Chem 279 2004 16463 16470
10. J. Heijenoort van Formation of glycan chains in the synthesis of bacterial peptidoglycan Glycobiol 11 2001 25R 36R
11. D.C. McPherson, and D.L. Popham Peptidoglycan biosynthesis in the absence of class A penicillin-binding proteins in Bacillus subtilis J Bacteriol 185 2003 1423 1431 All class A PBPs were deleted in B. subtilis. The resulting strain produces peptidoglycan, showing that there are as-yet unidentified transglycosylases.
12. A. Arbeloa, H. Segal, J.E. Hugonnet, N. Josseaume, L. Dubost, J.P. Brouard, L. Gutmann, D. Mengin-Lecreulx, and M. Arthur Role of class A penicillin-binding proteins in PBP5-mediated beta-lactam resistance in Enterococcus faecalis J Bacteriol 186 2004 1221 1228 All class A PBP genes were deleted in Enterococcus faecalis. The resulting strain is able to produce peptidoglycan and is resistant to moenomycin, suggesting that unknown TGs may give rise to resistance to TG inhibitors.
13. J.S. Anderson, M. Matsuhashi, M.A. Haskin, and J.L. Strominger Biosynthesis of the peptidoglycan of bacterial cell walls. Phospholipid carriers in the reaction sequence J Biol Chem 242 1967 3180 3190
14. X-Y. Ye, M. Lo, L. Brunner, D. Walker, D. Kahne, and S. Walker Better substrates for bacterial transglycosylases J Am Chem Soc 125 2001 8736 8737
15. B. Schwartz, J.A. Markwalder, and Y. Wang Lipid II: total synthesis of the bacterial cell wall precursor and utilization as a substrate for glycotransfer and transpeptidation by penicillin binding protein (PBP)1b of Escherichia coli J Am Chem Soc 123 2001 11638 11643
16. M.S. VanNiewenhze, S.C. Mauldin, M. Zia-Ebrahimi, B.E. Winger, W.J. Hornback, S.L. Saha, J.A. Aikins, and L.C. Blaszczak First total synthesis of lipid II: the final monomeric intermediate in bacterial cell wall biosynthesis J Am Chem Soc 124 2002 3656 3660
17. E. Breukink, H.E. van Heusden, P.J. Vollmerhaus, E. Swiezewska, L. Brunner, S. Walker, Heck AJR, and B. de Kruijff Lipid II is an intrinsic component of the pore induced by nisin in bacterial membranes J Biol Chem 278 2003 19898 19903
18. A.M.D. Guilmi, A. Dessen, O. Dideberg, and T. Vernet Bifunctional penicillin-binding proteins: focus on the glycosyltransferase domain and its specific inhibitor moenomycin Curr Pharm Biotechnol 3 2002 63 75
19. B. Schwartz, J.A. Markwalder, S.P. Seitz, Y. Wang, and R.L. Stein A kinetic characterization of the glycosyltransferase activity of Eschericia coli PBP1b and development of a continuous fluorescence assay Biochemistry 41 2002 12552 12561
20. L. Chen, D. Walker, B. Sun, Y. Hu, S. Walker, and D. Kahne Vancomycin analogues active against vanA-resistant strains inhibit bacterial transglycosylase without binding substrate Proc Natl Acad Sci USA 100 2003 5658 5663
21. D.S. Barrett, L. Chen, N.K. Litterman, and S. Walker Expression and characterization of the isolated glycosyltransferase module of Escherichia coli PBP1b Biochemistry 43 2004 12375 12381
22. Q.M. Wang, R.B. Peery, R.B. Johnson, W.E. Alborn, W.K. Yeh, and P.L. Skatrud Identification and characterization of a monofunctional glycosyltransferase from Staphylococcus aureus J Bacteriol 183 2001 4779 4785
23. A.M.D. Guilmi, A. Dessen, O. Dideberg, and T. Vernet The glycosyltransferase domain of penicillin-binding protein 2a from Streptococcus pneumoniae catalyzes the polymerization of murein glycan chains J Bacteriol 185 2003 4418 4423
24. D. Barrett, C. Leimkuhler, L. Chen, D. Walker, D. Kahne, and S. Walker Kinetic characterization of the glycosyltransferase module of Staphylococcus aureus PBP2 J Bacteriol 187 2005 2215 2217 The first report of successful overexpression and initial characterization of a TG with reasonable kinetic properties from a pathogenic microorganism.
25. M.G. Pinho, H. de Lencastre, and A. Tomasz An acquired and a native penicillin-binding protein cooperate in building the cell wall of drug-resistant staphylococci Proc Natl Acad Sci USA 98 2001 10886 10891
26. A.A. Branstrom, S. Midha, and R.C. Goldman In situ assay for identifying inhibitors of bacterial transglycosylase FEMS Microbiol Lett 191 2000 187 190
27. M.D.F.S. Barbosa, G. Yang, J. Fang, M.G. Kurilla, and D.L. Pompliano Development of a whole-cell assay for peptidoglycan biosynthesis inhibitors Antimicrob Agents Chemother 46 2002 943 946
28. B. Chandrakala, R.K. Shandil, U. Mehra, S. Ravishankar, P. Kaur, V. Usha, B. Joe, and S.M. de Sousa High-throughput screen for inhibitors of transglycosylase and/or transpeptidase activities of Escherichia coli penicillin binding protein 1b Antimicrob Agents Chemother 48 2004 30 40
29. M-C. Lo, H. Men, A. Branstrom, J. Helm, N. Yao, R. Goldman, and S. Walker A new mechanism proposed for ramoplanin J Am Chem Soc 122 2000 3540 3541
30. E.R. Baizman, A.A. Branstrom, C.B. Longley, N. Allanson, M.J. Sofia, D. Gange, and R.C. Goldman Antibacterial activity of synthetic analogues based on disaccharide structure of moenomycin, an inhibitor of bacterial transglycosylase Microbiology 146 2000 3129 3140
31. W. Vollmer, and J.-V. Holtje A simple screen for murein transglycosylase inhibitors Antimicrob Agents Chemother 44 2000 1181 1185
32. D. Sun, S. Cohen, N. Mani, C. Murphy, and D.M. Rothstein A pathway-specific cell based screening system to detect cell wall inhibitors J Antibiot 55 2002 279 287
33. M. De Cenzo, M. Kuranda, S. Cohen, J. Babiak, Z-D. Jiang, D. Sun, M. Hickey, P. Sancheti, P.A. Bradford, and P. Youngman Identification of compounds that inhibit late steps of peptidoglycan synthesis in bacteria J Antibiot 55 2002 288 295
34. Y. Hu, J.S. Helm, L. Chen, X.Y. Ye, and S. Walker Ramoplanin inhibits bacterial transglycosylases by binding as a dimer to lipid II J Am Chem Soc 125 2003 8736 8737
35. C. Leimkuhler, L. Chen, D. Barrett, G. Panzone, B. Sun, B. Falcone, M. Oberthur, S. Donadio, S. Walker, and D. Kahne Differential inhibition of Staphylococcus aureus PBP2 by glycopeptide antibiotics J Am Chem Soc 127 2005 3250 3251
36. D. Kahne, C. Leimkuhler, W. Lu, and C. Walsh Glycopeptide and lipoglycopeptide antibiotics Chem Rev 105 2005 425 448
37. S.-T.D. Hsu, E. Breukink, E. Tishchenko, M.A. Lutters, B. de Kruijff, R. Kaptein, A.M.J.J. Bonvin, and N.A.J. van Nuland The nisin-lipid II complex reveals a pyrophosphate cage that provides a blueprint for novel antibiotics Nat Struct Mol Biol 11 2004 963 967 The solution structure of a nisin-Lipid II complex is reported. The pyrophosphate cage responsible for the interaction is proposed to be a template for the development of novel drugs.
38. C. Chatterjee, M. Paul, L. Xie, and W.A. van der Donk Biosynthesis and mode of action of lantibiotics Chem Rev 105 2005 633 684
39. S. Walker, L. Chen, Y. Hu, Y. Rew, D. Shin, and D.L. Boger Chemistry and biology of ramoplanin: a lipoglycodepsipeptide with potent antibiotic activity Chem Rev 105 2005 449 476
40. H. Maki, K. Miura, and Y. Yamano Katanosin B and plusbacin A(3), inhibitors of peptidoglycan synthesis in methicillin-resistant Staphylococcus aureus Antimicrob Agents Chemother 45 2001 1823 1827
41. A. Ruzin, G. Singh, A. Severin, Y. Yang, R.G. Dushin, A.G. Sutherland, A. Minnick, M. Greenstein, M.K. May, D.M. Shlaes, and P.A. Bradford Mechanism of action of the mannopeptimycins, a novel class of glycopeptide antibiotics active against vancomycin-resistant Gram-positive bacteria Antimicrob Agents Chemother 48 2004 728 738 A novel family of glycopeptide antibiotics are reported and are proposed to bind Lipid II and inhibit TGs.
42. P. Welzel Transglycosylase inhibition K. Krohn H. Kirst H. Maag Antibiotics and Antiviral Compounds - Chemical Synthesis and Modification 1993 VCH 373 378
43. H. He, B. Shen, J. Korshalla, M.M. Siegel, and G.T. Carter Isolation and structural elucidation of AC326-alpha, a new member of the moenomycin group J Antibiot 53 2000 191 195
44. M. Kurz, W. Guba, and L. Vertesy Three-dimensional structure of moenomycin A -a potent inhibitor of penicillin-binding protein 1b Eur J Biochem 252 1998 500 507
45. T. Ruhl, M. Daghish, A. Buchynskyy, K. Barche, D. Volke, K. Stembera, U. Kempin, D. Knoll, L. Hennig, and M. Findeisen Studies on the interaction of the antibiotic moenomycin A with the enzyme penicillin-binding protein 1b Bioorg Med Chem 11 2003 2965 2981
46. H. He Mannopeptimycins, a novel class of glycopeptide antibiotics active against Gram-positive bacteria Appl Microbiol Biotechnol 2005 epub
47. D.L. Higgins, R.C. Chang, D.V. Debabov, J. Leung, T. Wu, K.M. Krause, E. Sandvik, J.M. Hubbard, K. Kaniga, and D.E. Schmidt Telavancin, a multifunctional lipoglycopeptide, disrupts both cell wall synthesis and cell membrane integrity in methicillin-resistant Staphylococcus aureus J Antimicrob Agents Chemother 49 2005 1127 1134 A novel lipoglycopeptide capable of interrupting cell wall biosynthesis and integrity is reported.
48. H.C. Losey, J. Jiang, J.B. Biggins, M. Oberthur, X.Y. Ye, S.D. Dong, D. Kahne, J.S. Thorson, and C.T. Walsh Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptides Chem Biol 9 2002 1305 1314
49. W. Lu, M. Oberthur, C. Leimkuhler, J. Tao, D. Kahne, and C.T. Walsh Characterization of a regiospecific epivancosaminyl transferase GtfA and enzymatic reconstitution of the antibiotic chloroeremomycin Proc Natl Acad Sci USA 101 2004 4390 4395
50. R.G. Kruger, W. Lu, M. Oberthur, J. Tao, D. Kahne, and C.T. Walsh Tailoring of glycopeptide scaffolds by the acyltransferases from the teicoplanin and A-40,926 biosynthetic operons Chem Biol 12 2005 131 140 The acyltransferase from the glycopeptide A-40926 gene cluster has been shown to be promiscuous. This feature of the enzyme can be exploited to produce novel acylated glycopeptides with improved therapeutic properties.
51. B. Bister, D. Bischoff, G.J. Nicholson, S. Stockert, J. Wink, C. Brunati, S. Donadio, S. Pelzer, W. Wohlleben, and R.D. Sussmuth Bromobalhimycin and chlorobromobalhimycins - illuminating the potential of halogenases in glycopeptide antibiotic biosyntheses ChemBioChem 4 2003 658 662
52. W. Jiang, J. Wanner, R.J. Lee, P.Y. Bounaud, and D.L. Boger Total synthesis of the ramoplanin A2 and ramoplanose aglycon J Am Chem Soc 19 2003 1877 1887
53. Y. Rew, D. Shin, I. Hwang, and D.L. Boger Total synthesis and examination of three key analogues of ramoplanin: a lipoglycodepsipeptide with potent antibiotic activity J Am Chem Soc 126 2004 1041 1043
54. L. Chen, Y. Yuan, J.S. Helm, Y. Hu, Y. Rew, D. Shin, D.L. Boger, and S. Walker Dissecting ramoplanin: mechanistic analysis of synthetic ramoplanin analogues as a guide to the design of improved antibiotics J Am Chem Soc 126 2004 7462 7463
55. M.J. Sofia, N. Allanson, N.T. Hatzenbuhler, R. Jain, R. Kakarla, N. Kogan, R. Liang, D. Liu, D.J. Silva, and H. Wang Discovery of novel disaccharide antibacterial agents using a combinatorial library approach J Med Chem 42 1999 3193 3198
56. R.C. Goldman, E.R. Baizman, A.A. Branstrom, and C.B. Longley Differential antibacterial activity of moenomycin analogues on Gram-positive bacteria Bioorg Med Chem Lett 10 2000 2251 2254
57. C. Miller, L.E. Thomsen, C. Gaggero, R. Mosseri, H. Ingmer, and S. Cohen SOS response induction by β-lactams and bacterial defense against antibiotic lethality Science 305 2004 1629 1631
58. S. Garneau, L. Qiao, L. Chen, S. Walker, and J.C. Vederas Synthesis of mono- and disaccharide analogs of moenomycin and lipid II for inhibition of transglycosylase activity of penicillin-binding protein 1b Bioorg Med Chem 12 2004 6473 6494
59. R. Kohli, C.T. Walsh, and M.D. Burkart Biomimetic synthesis and optimization of cyclic peptide antibiotics Nature 418 2002 658 661
60. X. Fu, C. Albermann, C. Zhang, and J.S. Thorson Diversifying vancomycin via chemoenzymatic strategies Org Lett 7 2005 113 115