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Chemical Compound Review

Ficaprenol     (2E,6E,10E,14E,18E,22E,26E,30E ,34E,38E)-3...

Synonyms: undecaprenol, CPD-188, CHEBI:16591, AC1NQX2P, AC1Q7BUC, ...
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Disease relevance of undecaprenol


High impact information on undecaprenol

  • In a previous study of the roles of the various exo gene products in succinoglycan biosynthesis, exoP, exoQ, and exoT mutants were found to synthesize undecaprenol-linked fully modified succinoglycan octasaccharide subunits, suggesting possible roles for their gene products in polymerization or transport [4].
  • The analysis of its catalytic properties clearly demonstrated that the purified BacA protein exhibited undecaprenyl pyrophosphate phosphatase activity but not undecaprenol phosphokinase activity [5].
  • The polyisoprenols (PIs) dolichol and undecaprenol function as chemical carriers of glycosyl residues in the membrane-directed synthesis of glycoconjugates in prokaryotic and eukaryotic cells [6].
  • RfbP encodes a galactosyl transferase enzyme that catalyses the transfer of galactose to undecaprenol phosphate, the initial step in O-polysaccharide synthesis [7].
  • Subsequent molecular analysis of a subset of these mutants identified genes encoding undecaprenol kinase, homoserine kinase, anaerobic ribonucleotide reductase, adenylosuccinate lyase, and a hypothetical protein [8].

Chemical compound and disease context of undecaprenol


Biological context of undecaprenol

  • Further analysis revealed that the product of the dgk gene in S. mutans predominantly recognizes a lipid substrate other than diacylglycerol, most likely undecaprenol, as demonstrated by its efficient phosphorylation and the resistance of the product of the reaction to saponification [2].
  • C55-Dolichol: occurrence in pig liver and preparation by hydrogenation of plant undecaprenol [9].
  • The bcrA and bcrB genes were organized in an operon with a third gene, bcrD, that had homology to undecaprenol kinases [10].
  • Its behavior on column and thin-layer chromatography, the rates of its hydrolysis in acid and base, and the response of its synthesis to inhibitors are all identical to the other sugar-lipid intermediates which have been shown to contain sugars attached to the C55-polyisoprenol, undecaprenol, by a pyrophosphate linkage [11].
  • We isolated a spontaneous suppressor mutant complementing the acid-sensitive phenotype of Streptococcus mutans strain Tn-1, a mutant previously generated in this laboratory, defective in the activity of the dgk-encoded putative undecaprenol kinase [12].

Anatomical context of undecaprenol


Associations of undecaprenol with other chemical compounds

  • Analyses of lipid II preparations by fast atom bombardment tandem mass spectroscopy (FAB-MS/MS) resulted in the identification of the lipid-carrier as the 55-carbon polyisoprenyl alcohol, undecaprenol [15].
  • The influence of undecaprenol on phosphatidylcholine macrovesicular bilayer lipid membranes has been studied by electrophysiological techniques [14].


  1. Synthesis of peptidoglycan by high molecular weight penicillin-binding proteins of Bacillus subtilis and Bacillus stearothermophilus. Jackson, G.E., Strominger, J.L. J. Biol. Chem. (1984) [Pubmed]
  2. The stress-responsive dgk gene from Streptococcus mutans encodes a putative undecaprenol kinase activity. Lis, M., Kuramitsu, H.K. Infect. Immun. (2003) [Pubmed]
  3. Lipid activation of undecaprenol kinase from Lactobacillus plantarum. Kalin, J.R., Allen, C.M. Biochim. Biophys. Acta (1980) [Pubmed]
  4. Biosynthetic control of molecular weight in the polymerization of the octasaccharide subunits of succinoglycan, a symbiotically important exopolysaccharide of Rhizobium meliloti. González, J.E., Semino, C.E., Wang, L.X., Castellano-Torres, L.E., Walker, G.C. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  5. The bacA gene of Escherichia coli encodes an undecaprenyl pyrophosphate phosphatase activity. El Ghachi, M., Bouhss, A., Blanot, D., Mengin-Lecreulx, D. J. Biol. Chem. (2004) [Pubmed]
  6. 2H NMR investigation of the organization and dynamics of polyisoprenols in membranes. de Ropp, J.S., Troy, F.A. J. Biol. Chem. (1985) [Pubmed]
  7. Identification of cpsD, a gene essential for type III capsule expression in group B streptococci. Rubens, C.E., Heggen, L.M., Haft, R.F., Wessels, M.R. Mol. Microbiol. (1993) [Pubmed]
  8. Identification of virulence determinants for endocarditis in Streptococcus sanguinis by signature-tagged mutagenesis. Paik, S., Senty, L., Das, S., Noe, J.C., Munro, C.L., Kitten, T. Infect. Immun. (2005) [Pubmed]
  9. C55-Dolichol: occurrence in pig liver and preparation by hydrogenation of plant undecaprenol. Mańkowski, T., Jankowski, W., Chojnacki, T., Franke, P. Biochemistry (1976) [Pubmed]
  10. Acquired bacitracin resistance in Enterococcus faecalis is mediated by an ABC transporter and a novel regulatory protein, BcrR. Manson, J.M., Keis, S., Smith, J.M., Cook, G.M. Antimicrob. Agents Chemother. (2004) [Pubmed]
  11. Role of a sugar-lipid intermediate in colanic acid synthesis by Escherichia coli. Johnson, J.G., Wilson, D.B. J. Bacteriol. (1977) [Pubmed]
  12. Characterization of a suppressor mutation complementing an acid-sensitive mutation in Streptococcus mutans. Lis, M., Kuramitsu, H.K. FEMS Microbiol. Lett. (2003) [Pubmed]
  13. Regulation of LiaRS-dependent gene expression in bacillus subtilis: identification of inhibitor proteins, regulator binding sites, and target genes of a conserved cell envelope stress-sensing two-component system. Jordan, S., Junker, A., Helmann, J.D., Mascher, T. J. Bacteriol. (2006) [Pubmed]
  14. The effect of undecaprenol on bilayer lipid membranes. Janas, T., Chojnacki, T., Swiezewska, E., Janas, T. Acta Biochim. Pol. (1994) [Pubmed]
  15. Characterization of the lipid-carrier involved in the synthesis of enterobacterial common antigen (ECA) and identification of a novel phosphoglyceride in a mutant of Salmonella typhimurium defective in ECA synthesis. Rick, P.D., Hubbard, G.L., Kitaoka, M., Nagaki, H., Kinoshita, T., Dowd, S., Simplaceanu, V., Ho, C. Glycobiology (1998) [Pubmed]
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