Inhibitors for bacterial cell-wall recycling

ACS Medicinal Chemistry Letters

Volumn 3, Issue 3, 2012, Pages 238-242

  Yamaguchi, Takao ^a   Blázquez, Blas ^a   Hesek, Dusan ^a   Lee, Mijoon ^a   Llarrull, Leticia I ^a   Boggess, Bill ^a   Oliver, Allen G ^a   Fisher, Jed F ^a   Mobashery, Shahriar ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

Iminosaccharide; MltB; NagZ; peptidoglycan; lactam

Indexed keywords

GLYCOSYLTRANSFERASE; N ACETYLGLUCOSAMINE; TETRAPROPYLAMMONIUM;

ARTICLE; BACTERIAL CELL WALL; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; CYTOPLASM; NONHUMAN; PRIORITY JOURNAL; THERMODYNAMICS;

BACTERIA (MICROORGANISMS); NEGIBACTERIA;

EID: 84863294000     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml2002746     Document Type: Article

References (42)

1. Park, J. T.; Uehara, T. How bacteria consume their own exoskeletons (turnover and recycling of cell wall peptidoglycan) Microbiol. Mol. Biol. Rev. 2008, 72, 211-227 (Pubitemid 351822290)
2. Lee, M.; Zhang, W.; Hesek, D.; Noll, B. C.; Boggess, B.; Mobashery, S. Bacterial AmpD at the crossroads of peptidoglycan recycling and manifestation of antibiotic resistance J. Am. Chem. Soc. 2009, 131, 8742-8743
3. Hesek, D.; Lee, M.; Zhang, W.; Noll, B. C.; Mobashery, S. Total synthesis of N -acetylglucosamine-1,6-anhydro- N -acetylmuramylpentapeptide and evaluation of its turnover by AmpD from Citrobacter freundii J. Am. Chem. Soc. 2009, 131, 5187-5193
4. Compain, P.; Martin, O. R., Eds.; Iminosugars: From synthesis to therapeutic applications; Wiley-VCH: Weinheim, 2007.
5. Kajimoto, T.; Liu, K. K. C.; Pederson, R. L.; Zhong, Z.; Ichikawa, Y.; Porco, J. A., Jr.; Wong, C.-H. Enzyme-catalyzed aldol condensation for asymmetric synthesis of azasugars: synthesis, evaluation, and modeling of glycosidase inhibitors J. Am. Chem. Soc. 1991, 113, 6187-6196
6. Fleet, G. W. J.; Smith, P. W.; Nash, J.; Fellows, L. E.; Parekh, R. B.; Rademacher, T. W. Synthesis of 2-acetamido-1,5-imino-1,2,5-trideoxy- d -mannitol and of 2-acetamido-1,5-imino-1,2,5-trideoxy- d -glucitol, a potent and specific inhibitor of a number of β- N -acetylglucosaminidases Chem. Lett. 1986, 1051-1054
7. BoÌ̂shagen, H.; Heiker, F.-R.; SchuÌ̂ller, A. M. The chemistry of the 1-deoxynojirimycin system. Synthesis of 2-acetamido-1,2-dideoxynojirimycin from 1-deoxynojirimycin Carbohydr. Res. 1987, 164, 141-148
8. Kappes, E.; Legler, G. Synthesis and inhibitory properties of 2-acetamido-2-deoxynojirimycin (2-acetamido-5-amino-2.5-dideoxy- d -glucopyranose, 1) and 2-acetamido-1.2-dideoxynojirimycin (2-acetamido-1,5- imino1,2,5-trideoxy- d -glucitol, 2) J. Carbohydr. Chem. 1989, 8, 371-388 (Pubitemid 19185978)
9. Ishida, H.; Kitagawa, M.; Kiso, M.; Hasegawa, A.; Azuma, I. Synthesis and immunoadjuvant activity of N -[2- O -(2-acetamido-1,2,3,5-tetradeoxy-1,5-imino- d -glucitol-3-yl)- d -lactoyl]- l -alanyl- d -isoglutamine Carbohydr. Res. 1990, 208, 267-272
10. Kiso, M.; Kitagawa, M.; Ishida, H.; Hasegawa, A. Studies on glycan processing inhibitorsî - ̧synthesis of N -acethylhexosamine of N -acetylhexosamine analogs and cyclic carbamate derivatives of 1-deoxynojirimycin J. Carbohydr. Chem. 1991, 10, 25-45
11. Furneaux, R. H.; Gainsford, G. J.; Lynch, G. P.; Yorke, S. C. 2-Acetamido-1,2-dideoxynojirimycin: an improved synthesis Tetrahedron 1993, 49, 9605-9612
12. Gradnig, G.; Legler, G.; StuÌ̂tz, A. E. A novel approach to the 1-deoxynojirimycin system: synthesis from sucrose of 2-acetamido-1,2- dideoxynojirimycin, as well as some 2- N -modified derivatives Carbohydr. Res. 1996, 287, 49-57 (Pubitemid 26199238)
13. Patil, N. T.; John, S.; Sabharwal, S. G.; Dhavale, D. D. 1-Aza-sugars from d -glucose. Preparation of 1-deoxy-5-dehydroxymethyl-nojirimycin, its analogues and evaluation of glycosidase inhibitory activity Bioorg. Med. Chem. 2002, 10, 2155-2160 (Pubitemid 34450905)
14. Swaleh, S.; Liebscher, J. New strategy for the synthesis of iminoglycitols from amino acids J. Org. Chem. 2002, 67, 3184-3193 (Pubitemid 34517695)
15. Al-Rawi, S.; Hinderlich, S.; Reutter, W.; Giannis, A. New strategy for the synthesis of iminoglycitols from amino acids Angew. Chem., Int. Ed. 2004, 43, 4366-4370
16. Steiner, A. J.; Schitter, G.; StuÌ̂tz, A. E.; Wrodnigg, T. M.; Tarling, C. A.; Withers, S. G.; Mahuran, D. J.; Tropak, M. B. 2-Acetamino-1,2-dideoxynojirimycinî - ̧lysine hybrids as hexosaminidase inhibitors Tetrahedron: Asymmetry 2009, 20, 832-835
17. Overkleeft, H. S.; van Wiltenburg, J.; Pandit, U. K. An expedient stereoselective synthesis of gluconolactam Tetrahedron Lett. 1993, 34, 2527-2528
18. Granier, T.; Vasella, A. Synthesis and some transformations of 2-Acetamido-5-amino-3,4,6-tri- O -benzyl-2,5-dideoxy- d -glucono-1,5-lactam Helv. Chim. Acta 1998, 81, 865-880 (Pubitemid 128497278)
19. van den Berg, R. J. B. H. N.; Noort, D.; Milder-Enacache, E. S.; van der Marel, G. A.; van Boom, J. H.; Benschop, H. P. Approach toward a generic treatment of gram-negative infections: synthesis of haptens for catalytic antibody mediated cleavage of the interglycosidic bond in lipid A Eur. J. Org. Chem. 1999, 2593-2600
20. Ho, C.-W.; Popat, S. D.; Liu, T.-W.; Tsai, K.-C.; Ho, M.-J.; Chen, W.-H.; Yang, A.-S.; Lin, C.-H. Development of GlcNAc-inspired iminocyclitiols as potent and selective N -acetyl-beta-hexosaminidase inhibitors ACS Chem. Biol. 2010, 5, 489-497
21. Berger, I.; Nazarov, A. A.; Hartinger, C. G.; Groessl, M.; Valiahdi, S.-M.; Jakupec, M. A.; Keppler, B. K. A glucose derivative as natural alternative to the cyclohexane-1,2-diamine ligand in the anticancer drug oxaliplatin? ChemMedChem 2007, 2, 505-514
22. Babic̜, A.; Pec̜ar, S. Total synthesis of uridine diphosphate- N -acetylmuramoyl- l -alanine Tetrahedron: Asymmetry 2008, 19, 2265-2271
23. Yamaguchi, T.; Hesek, D.; Lee, M.; Oliver, A. G.; Mobashery, S. Sulfonylation-induced N-to O -acetyl migration in 2-acetamidoethanol derivatives J. Org. Chem. 2010, 75, 3515-3517
24. Suvorov, M.; Lee, M.; Hesek, D.; Boggess, B.; Mobashery, S. Lytic transglycosylase MltB of Escherichia coli and its role in recycling of peptidoglycan strands of bacterial cell wall J. Am. Chem. Soc. 2008, 130, 11878-11879
25. Vollmer, W.; Joris, B.; Charlier, P.; Foster, S. Bacterial peptidoglycan (murein) hydrolases FEMS Microbiol. Rev. 2008, 32, 259-286 (Pubitemid 351257818)
26. Scheurwater, E.; Reid, C. W.; Clarke, A. J. Lytic transglycosylases: bacterial space-making autolysins Int. J. Biochem. Cell Biol. 2008, 40, 586-591 (Pubitemid 351288584)
27. Thunnissen, A-M. W. H.; Rozeboom, H. J.; Kalk, K. H.; Dijkstra, B. W. Structure of the 70-kDa soluble lytic transglycosylase complexed with bulgecin A. Implications for the enzymatic mechanism Biochemistry 1995, 34, 12729-12737
28. VoÌ̂tsch, W.; Templin, M. F. Characterization of a β- N -acetylglucosaminidase of Escherichia coli and elucidation of its role in muropeptide recycling and β -lactamase induction J. Biol. Chem. 2000, 275, 39032-39038 (Pubitemid 32058916)
29. Cheng, Q.; Li, H.; Merdek, K.; Park, J. T. Molecular characterization of the β- N -acetylglucosaminidase of Escherichia coli and its role in cell wall recycling J. Bacteriol. 2000, 182, 4836-4840 (Pubitemid 30641806)
30. Plumbridge, J. An alternative route for recycling of N -acetylglucosamine from peptidoglycan involves the N -acetylglucosamine phosphotransferase system in Escherichia coli J. Bacteriol. 2009, 191, 5641-5647
31. Uehara, T.; Park, J. T. Role of the murein precursor UDP- N -acetylmuramyl- l -Ala-gamma- d -Glu-meso-diaminopimelic acid- d -Ala- d -Ala in repression of β-lactamase induction in cell division mutants J. Bacteriol. 2002, 184, 4233-4239 (Pubitemid 34774304)
32. Stubbs, K. A.; Balcewich, M.; Mark, B. L.; Vocadlo, D. J. Small molecule inhibitors of a glycoside hydrolase attenuate inducible AmpC-mediated β-lactam resistance J. Biol. Chem. 2007, 282, 21382-21391 (Pubitemid 47099917)
33. Asgarali, A.; Stubbs, K. A.; Oliver, A.; Vocadlo, D. J.; Mark, B. L. Inactivation of the glycoside hydrolase NagZ attenuates antipseudomonal β-lactam resistance in Pseudomonas aeruginosa Antimicrob. Agents Chemother. 2009, 53, 2274-2282
34. Zamorano, L.; Reeve, T. M.; Deng, L.; Juan, C.; Moya, B.; Cabot, G.; Vocadlo, D. J.; Mark, B. L.; Oliver, A. NagZ inactivation prevents and reverts β-lactam resistance, driven by AmpD and PBP 4 mutations in Pseudomonas aeruginosa Antimicrob. Agents Chemother. 2010, 54, 3557-3563
35. Balcewich, M. D.; Stubbs, K. A.; He, Y.; James, T. W.; Davies, G. J.; Vocadlo, D. J.; Mark, B. L. Insight into a strategy for attenuating AmpC-mediated β-lactam resistance: structural basis for selective inhibition of the glycoside hydrolase NagZ Protein Sci. 2009, 18, 1541-1551
36. Stubbs, K. A.; Scaffidi, A.; Debowski, A. W.; Mark, B. L.; Stick, R. V.; Vocadlo, D. J. Synthesis and use of mechanism-based protein-profiling probes for retaining β- d -glucosaminidases facilitate identification of Pseudomonas aeruginosa NagZ J. Am. Chem. Soc. 2008, 130, 327-335
37. Choubdar, N.; Bhat, R. G.; Stubbs, K. A.; Yuzwa, S.; Pinto, B. M. Synthesis of 2-amido, 2-amino, and 2-azido derivatives of the nitrogen analogue of the naturally occurring glycosidase inhibitor salacinol and their inhibitory activities against O -GlcNAcase and NagZ enzymes Carbohydr. Res. 2008, 343, 1766-1777
38. Davis, B. G. A silver-lined anniversary of Fleet iminosugars: 1984-2009, from DIM to DRAM to LABNAc Tetrahedron: Asymmetry 2009, 20, 652-671
39. Orth, R.; Pitscheider, M.; Sieber, S. A. Chemical probes for the labeling of the bacterial glucosaminidase NagZ via the Huisgen cycloaddition Synthesis 2010, 2201-2206
40. Litzinger, S.; Duckworth, A.; Nitzsche, K.; Risinger, C.; Wittmann, V.; Mayer, C. Muropeptide rescue in Bacillus subtilis involves sequential hydrolysis by β- N -acetylglucosaminidase and N -acetylmuramyl- l -alanine amidase J. Bacteriol. 2010, 192, 3132-3143
41. Litzinger, S.; Fischer, S.; Polzer, P.; Diederichs, K.; Welte, W.; Mayer, C. Structural and kinetic analysis of Bacillus subtilis N - acetylglucosaminidase reveals a unique Asp-His dyad mechanism J. Biol. Chem. 2010, 285, 35675-35684
42. Llarrull, L. I.; Testero, S. A.; Fisher, J. F.; Mobashery, S. The future of the β-lactams Curr. Opin. Microbiol. 2010, 13, 551-557