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Chemical Compound Review

AC1LCUYG     5-acetamido-6-[5-acetamido-4- hydroxy-6...

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Disease relevance of lipid II


High impact information on lipid II

  • Use of the cell wall precursor lipid II by a pore-forming peptide antibiotic [6].
  • We have also found that moenomycin is not competitive with respect to the lipid II substrate of PBP1b, as has long been believed [7].
  • It is demonstrated that colicin M exhibits both in vitro and in vivo enzymatic properties of degradation of lipid I and lipid II peptidoglycan intermediates [8].
  • Several members utilize a unique mode of biological action that involves the sequestration of lipid II, a crucial intermediate in peptidoglycan biosynthesis, to form pores in bacterial membranes [9].
  • The effect of the dimerization of PBP1B on its activities was studied with a newly developed in vitro murein synthesis assay with radioactively labeled lipid II precursor as substrate [10].

Chemical compound and disease context of lipid II


Biological context of lipid II

  • In light of the emerging antibiotic resistance problems, an understanding of the specific recognition mechanism of nisin with lipid II at the residue specific level may therefore aid in the development of novel antibiotics [13].
  • Thus, the interaction of mersacidin with lipid II apparently occurs via a binding site which is not targeted by any antibiotic currently in use [14].
  • These phenotypes suggest that the accumulation of lipid II perturbs the structure of the bacterial outer membrane [15].
  • Cyanelle envelope membrane preparations were shown to catalyze the lipid-linked steps of peptidoglycan biosynthesis as well as the putrescinylation and subsequent acetylation, occurring at the stage of lipid I and/or lipid II [16].
  • Both peptides share a conserved sequence motif with plantaricin C and pediocin PD-1, which is most probably involved in the binding of these bacteriocins to lipid II [17].

Anatomical context of lipid II

  • However, it was not known whether Lipid II functions only as a receptor to recruit nisin to bacterial membranes, thus increasing its specificity for bacterial cells, or whether it also plays a role in pore formation [18].
  • We propose a mode of action model in which LtnA1 first interacts specifically with lipid II in the outer leaflet of the bacterial cytoplasmic membrane [19].
  • Lipid-I and lipid-II can be separated from clear cytosol by ultracentrifugation and gel filtration respectively [20].
  • No correlation was observed between the maximal Lipid II pool and nisin sensitivity, as was further corroborated by using spheroplasts of nisin-resistant and wild-type strains of M. flavus, which were equally sensitive to nisin [21].
  • 1. A second novel globoside, provisionally named Lipid II in the previous study, was obtained from spermatozoa of the fresh-water bivalve, Hyriopsis schlegelii [22].

Associations of lipid II with other chemical compounds


Gene context of lipid II

  • Accumulation of the enterobacterial common antigen lipid II biosynthetic intermediate stimulates degP transcription in Escherichia coli [15].
  • Rather, the wecE, rmlAECA, and wecF null mutations each impede the same step in ECA biosynthesis, and it is the accumulation of the ECA biosynthetic intermediate, lipid II, that causes the observed perturbations [15].
  • The data support the conclusion that accumulation of lipid II is responsible in some way for the hypersensitivity of delta rfbA mutants to SDS [26].
  • As additional proof that induction of beta-lactamase is the direct result of cell wall inhibition, a host strain carrying a temperature-sensitive mutation in the murG gene, whose product converts the cell wall intermediate Lipid I, to Lipid II, also induced beta-lactamase at the restrictive temperature [27].
  • In the first step, radiolabeled lipid II, the TG substrate, was made in membranes of the E. coli ponB::Spc(r) strain by incubation with the peptidoglycan sugar precursors [28].

Analytical, diagnostic and therapeutic context of lipid II

  • A novel synthesized water-soluble variant of lipid II (LII) was used to evaluate the noncovalent interactions between a number of glycopeptide antibiotics and their receptor by bioaffinity electrospray ionization mass spectrometry (ESI-MS) [29].
  • The binding to lipid II was studied through (15)N-(1)H HSQC titration, backbone amide proton temperature coefficient analysis, and heteronuclear (15)N[(1)H]-NOE relaxation dynamics experiments [13].
  • Transduction of wild-type rff genes into the mutant restored the ability to synthesize both lipid II and ECA as determined by in vitro assay and Western blot (immunoblot) analyses done with anti-ECA monoclonal antibody, respectively [30].


  1. Anchoring of surface proteins to the cell wall of Staphylococcus aureus. III. Lipid II is an in vivo peptidoglycan substrate for sortase-catalyzed surface protein anchoring. Perry, A.M., Ton-That, H., Mazmanian, S.K., Schneewind, O. J. Biol. Chem. (2002) [Pubmed]
  2. Lipid II: total synthesis of the bacterial cell wall precursor and utilization as a substrate for glycosyltransfer and transpeptidation by penicillin binding protein (PBP) 1b of Escherichia coli. Schwartz, B., Markwalder, J.A., Wang, Y. J. Am. Chem. Soc. (2001) [Pubmed]
  3. The first total synthesis of lipid II: the final monomeric intermediate in bacterial cell wall biosynthesis. VanNieuwenhze, M.S., Mauldin, S.C., Zia-Ebrahimi, M., Winger, B.E., Hornback, W.J., Saha, S.L., Aikins, J.A., Blaszczak, L.C. J. Am. Chem. Soc. (2002) [Pubmed]
  4. Acceptor Substrate Selectivity and Kinetic Mechanism of Bacillus subtilis TagA. Zhang, Y.H., Ginsberg, C., Yuan, Y., Walker, S. Biochemistry (2006) [Pubmed]
  5. Lipid II-based antimicrobial activity of the lantibiotic plantaricin C. Wiedemann, I., Böttiger, T., Bonelli, R.R., Schneider, T., Sahl, H.G., Martínez, B. Appl. Environ. Microbiol. (2006) [Pubmed]
  6. Use of the cell wall precursor lipid II by a pore-forming peptide antibiotic. Breukink, E., Wiedemann, I., van Kraaij, C., Kuipers, O.P., Sahl, H., de Kruijff, B. Science (1999) [Pubmed]
  7. Vancomycin analogues active against vanA-resistant strains inhibit bacterial transglycosylase without binding substrate. Chen, L., Walker, D., Sun, B., Hu, Y., Walker, S., Kahne, D. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  8. Colicin M exerts its bacteriolytic effect via enzymatic degradation of undecaprenyl phosphate-linked peptidoglycan precursors. El Ghachi, M., Bouhss, A., Barreteau, H., Touzé, T., Auger, G., Blanot, D., Mengin-Lecreulx, D. J. Biol. Chem. (2006) [Pubmed]
  9. New developments in lantibiotic biosynthesis and mode of action. Patton, G.C., van der Donk, W.A. Curr. Opin. Microbiol. (2005) [Pubmed]
  10. In vitro murein peptidoglycan synthesis by dimers of the bifunctional transglycosylase-transpeptidase PBP1B from Escherichia coli. Bertsche, U., Breukink, E., Kast, T., Vollmer, W. J. Biol. Chem. (2005) [Pubmed]
  11. Kinetic characterization of the glycosyltransferase module of Staphylococcus aureus PBP2. Barrett, D., Leimkuhler, C., Chen, L., Walker, D., Kahne, D., Walker, S. J. Bacteriol. (2005) [Pubmed]
  12. Further evidence that a cell wall precursor [C(55)-MurNAc-(peptide)-GlcNAc] serves as an acceptor in a sorting reaction. Ruzin, A., Severin, A., Ritacco, F., Tabei, K., Singh, G., Bradford, P.A., Siegel, M.M., Projan, S.J., Shlaes, D.M. J. Bacteriol. (2002) [Pubmed]
  13. Mapping the targeted membrane pore formation mechanism by solution NMR: the nisin Z and lipid II interaction in SDS micelles. Hsu, S.T., Breukink, E., de Kruijff, B., Kaptein, R., Bonvin, A.M., van Nuland, N.A. Biochemistry (2002) [Pubmed]
  14. The lantibiotic mersacidin inhibits peptidoglycan synthesis by targeting lipid II. Brötz, H., Bierbaum, G., Leopold, K., Reynolds, P.E., Sahl, H.G. Antimicrob. Agents Chemother. (1998) [Pubmed]
  15. Accumulation of the enterobacterial common antigen lipid II biosynthetic intermediate stimulates degP transcription in Escherichia coli. Danese, P.N., Oliver, G.R., Barr, K., Bowman, G.D., Rick, P.D., Silhavy, T.J. J. Bacteriol. (1998) [Pubmed]
  16. In vitro synthesis of peptidoglycan precursors modified with N-acetylputrescine by Cyanophora paradoxa cyanelle envelope membranes. Pfanzagl, B., Löffelhardt, W. J. Bacteriol. (1999) [Pubmed]
  17. Mode of action of lipid II-targeting lantibiotics. Bauer, R., Dicks, L.M. Int. J. Food Microbiol. (2005) [Pubmed]
  18. Lipid II is an intrinsic component of the pore induced by nisin in bacterial membranes. Breukink, E., van Heusden, H.E., Vollmerhaus, P.J., Swiezewska, E., Brunner, L., Walker, S., Heck, A.J., de Kruijff, B. J. Biol. Chem. (2003) [Pubmed]
  19. The mode of action of the lantibiotic lacticin 3147--a complex mechanism involving specific interaction of two peptides and the cell wall precursor lipid II. Wiedemann, I., Böttiger, T., Bonelli, R.R., Wiese, A., Hagge, S.O., Gutsmann, T., Seydel, U., Deegan, L., Hill, C., Ross, P., Sahl, H.G. Mol. Microbiol. (2006) [Pubmed]
  20. Non-esterified cholesterol-rich adrenal lipid fractions. Preparation, properties and preferential utilization for cholesterol side-chain cleavage by corticotropin-stimulated adrenal mitochondria. Farese, R.V., Prudente, W.J., Chuang, L.T. Biochem. J. (1980) [Pubmed]
  21. Resistance of Gram-positive bacteria to nisin is not determined by lipid II levels. Kramer, N.E., Smid, E.J., Kok, J., de Kruijff, B., Kuipers, O.P., Breukink, E. FEMS Microbiol. Lett. (2004) [Pubmed]
  22. Studies on glycosphingolipids of fresh-water bivalves. IV. Structure of a branched globoside containing mannose from spermatozoa of the fresh-water bivalve, Hyriopsis schlegelii. Hori, T., Takeda, H., Sugita, M., Itasaka, O. J. Biochem. (1977) [Pubmed]
  23. Nisin-induced changes in Bacillus morphology suggest a paradigm of antibiotic action. Hyde, A.J., Parisot, J., McNichol, A., Bonev, B.B. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  24. NMR study of mersacidin and lipid II interaction in dodecylphosphocholine micelles. Conformational changes are a key to antimicrobial activity. Hsu, S.T., Breukink, E., Bierbaum, G., Sahl, H.G., de Kruijff, B., Kaptein, R., van Nuland, N.A., Bonvin, A.M. J. Biol. Chem. (2003) [Pubmed]
  25. Biosynthesis of enterobacterial common antigen in Escherichia coli. In vitro synthesis of lipid-linked intermediates. Barr, K., Rick, P.D. J. Biol. Chem. (1987) [Pubmed]
  26. Accumulation of a lipid-linked intermediate involved in enterobacterial common antigen synthesis in Salmonella typhimurium mutants lacking dTDP-glucose pyrophosphorylase. Rick, P.D., Wolski, S., Barr, K., Ward, S., Ramsay-Sharer, L. J. Bacteriol. (1988) [Pubmed]
  27. A pathway-specific cell based screening system to detect bacterial cell wall inhibitors. Sun, D., Cohen, S., Mani, N., Murphy, C., Rothstein, D.M. J. Antibiot. (2002) [Pubmed]
  28. Screen for Inhibitors of the Coupled Transglycosylase-Transpeptidase of Peptidoglycan Biosynthesis in Escherichia coli. Ramachandran, V., Chandrakala, B., Kumar, V.P., Usha, V., Solapure, S.M., de Sousa, S.M. Antimicrob. Agents Chemother. (2006) [Pubmed]
  29. Getting closer to the real bacterial cell wall target: biomolecular interactions of water-soluble lipid II with glycopeptide antibiotics. Vollmerhaus, P.J., Breukink, E., Heck, A.J. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  30. Characterization of an Escherichia coli rff mutant defective in transfer of N-acetylmannosaminuronic acid (ManNAcA) from UDP-ManNAcA to a lipid-linked intermediate involved in enterobacterial common antigen synthesis. Barr, K., Ward, S., Meier-Dieter, U., Mayer, H., Rick, P.D. J. Bacteriol. (1988) [Pubmed]
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