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Chemical Compound Review

Skikimic acid     3,4,5-trihydroxycyclohexene- 1-carboxylic acid

Synonyms: SureCN43376, AGN-PC-006Z8H, AG-K-75912, ANW-43823, NSC-59257, ...
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Disease relevance of shikimic acid

  • Furthermore, we discuss the evolutionary and metabolic implications of the presence of two shikimate dehydrogenases in E. coli and other organisms [1].
  • Crystal structure of a novel shikimate dehydrogenase from Haemophilus influenzae [2].
  • Purification and characterization of shikimate kinase enzyme activity in Bacillus subtilis [3].
  • A cDNA encoding potato (Solanum tuberosum L.) 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase, the first enzyme of the shikimate pathway, was cloned into phage lambda gt11 [4].
  • Here we report such an operon organization in a cyanobacterium (Synechocystis PCC6803) involving the genes for four RPs that are important in the GTPase function of the ribosome and the aroC gene encoding chorismate synthase, a key enzyme in the shikimate pathway for biosynthesis of aromatic amino acids and cell wall components [5].

High impact information on shikimic acid

  • Genes encoding chorismate synthase, the final shikimate pathway enzyme, were cloned from T. gondii and P. falciparum [6].
  • This enzyme is a potential target for new antifungal and antibacterial drugs as the shikimate pathway is absent from mammals and DHQS is required for pathogen virulence [7].
  • Downregulation of ODO1 in transgenic P. hybrida Mitchell plants strongly reduced volatile benzenoid levels through decreased synthesis of precursors from the shikimate pathway [8].
  • Several of the assays, including those for sucrose phosphate synthase, ADP glucose pyrophosphorylase (AGPase), ferredoxin-dependent glutamate synthase, glycerokinase, and shikimate dehydrogenase, provide large advantages over previous approaches [9].
  • Transketolase (TK) catalyzes reactions in the Calvin cycle and the oxidative pentose phosphate pathway (OPPP) and produces erythrose-4-phosphate, which is a precursor for the shikimate pathway leading to phenylpropanoid metabolism [10].

Chemical compound and disease context of shikimic acid


Biological context of shikimic acid

  • Glyphosate-based herbicides, such as Roundup, target the shikimate pathway enzyme 5-enolpyruvylshikimate 3-phosphate (EPSP) synthase, the functionality of which is absolutely required for the survival of plants [15].
  • Hence, they integrate plastidial pathways, such as photosynthesis, starch biosynthesis, the oxidative pentose phosphate pathway and the shikimate pathway, into the metabolic network of plant cells [16].
  • We report the dramatic changes which occur to the shikimate pathway enzyme dehydroquinase when ligand is attached to its active site after borohydride reduction of the mechanistically important Schiff's base intermediates [17].
  • This is the first study that describes the crystal structure as well as mutagenesis and mechanistic analysis of this new class of shikimate dehydrogenase [2].
  • These results present the first biochemical/molecular genetic evidence of shikimate pathway in the cyanobacterial group [5].

Anatomical context of shikimic acid

  • MurA catalyzes the first step in the biosynthesis of the bacterial cell wall; AroA is the sixth enzyme of the shikimate pathway leading to the synthesis of aromatic compounds in numerous microorganisms and plants [18].
  • Activities of five other shikimate pathway enzymes were, however, similar in the adapted and nonadapted cells, and the concentrations of the free aromatic amino acids in the two cell lines were also similar [19].
  • A functional AtPPT1 providing plastids with PEP for the shikimate pathway is therefore essential for correct leaf development [20].
  • B6C3HF1 mouse vibrissae follicles were cultured in serum-free medium for 7 days at 31 degrees C. Follicles treated with water-soluble (WS) extracts of the leaves, fruits and roots of Illicium anisatum or shikimic acid grew significantly longer than controls [21].
  • This suggests that chorismate, a metabolite of the shikimate pathway, is present not only in the plastids but also in the cytosol of plant cells [22].

Associations of shikimic acid with other chemical compounds

  • We show that p-coumaroyl-CoA and caffeoyl-CoA are the best acyl group donors and that the acyl group is transferred more efficiently to shikimate than to quinate [23].
  • For example, feedback-regulated enzymes of the shikimate pathway are anthranilate synthase on the branch leading to Trp and chorismate mutase on the branch leading to Phe and Tyr [24].
  • In Neurospora, five structural and two regulatory genes mediate the initial events in quinate/shikimate metabolism as a carbon source [25].
  • Phenylalanine uptake into the root, its root-to-shoot translocation, and Phe and phenylpropanoid contents were unaltered in pig1-1, indicating that pig1-1 is not affected in amino acid translocation or the shikimate pathway [24].
  • There was also an increase in shikimate as a precursor of secondary plant products and marked changes in the levels of the minor sugars involved in ascorbate synthesis and cell wall metabolism [26].

Gene context of shikimic acid


Analytical, diagnostic and therapeutic context of shikimic acid

  • We have identified the interaction of EPSP synthase with one of its two substrates (shikimate 3-phosphate) and with the widely used herbicide glyphosate by x-ray crystallography [32].
  • Primary sequence analyses of BzdR showed an unusual modular organization with an N-terminal region homologous to members of the HTH-XRE family of transcriptional regulators and a C-terminal region similar to shikimate kinases [33].
  • The transition from reserve accumulation to seed desiccation was associated with a major metabolic switch, resulting in the accumulation of distinct sugars, organic acids, nitrogen-rich amino acids, and shikimate-derived metabolites [34].
  • The results of Northern and Southern blot analyses are consistent with the existence of only one shikimate kinase gene per haploid genome in tomato [35].
  • The shikimate pathway presents an attractive target for malaria chemotherapy [36].


  1. Structures of shikimate dehydrogenase AroE and its Paralog YdiB. A common structural framework for different activities. Michel, G., Roszak, A.W., Sauvé, V., Maclean, J., Matte, A., Coggins, J.R., Cygler, M., Lapthorn, A.J. J. Biol. Chem. (2003) [Pubmed]
  2. Crystal structure of a novel shikimate dehydrogenase from Haemophilus influenzae. Singh, S., Korolev, S., Koroleva, O., Zarembinski, T., Collart, F., Joachimiak, A., Christendat, D. J. Biol. Chem. (2005) [Pubmed]
  3. Purification and characterization of shikimate kinase enzyme activity in Bacillus subtilis. Huang, L., Montoya, A.L., Nester, E.W. J. Biol. Chem. (1975) [Pubmed]
  4. A cDNA encoding 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase from Solanum tuberosum L. Dyer, W.E., Weaver, L.M., Zhao, J.M., Kuhn, D.N., Weller, S.C., Herrmann, K.M. J. Biol. Chem. (1990) [Pubmed]
  5. A novel operon organization involving the genes for chorismate synthase (aromatic biosynthesis pathway) and ribosomal GTPase center proteins (L11, L1, L10, L12: rplKAJL) in cyanobacterium Synechocystis PCC 6803. Schmidt, J., Bubunenko, M., Subramanian, A.R. J. Biol. Chem. (1993) [Pubmed]
  6. Evidence for the shikimate pathway in apicomplexan parasites. Roberts, F., Roberts, C.W., Johnson, J.J., Kyle, D.E., Krell, T., Coggins, J.R., Coombs, G.H., Milhous, W.K., Tzipori, S., Ferguson, D.J., Chakrabarti, D., McLeod, R. Nature (1998) [Pubmed]
  7. Structure of dehydroquinate synthase reveals an active site capable of multistep catalysis. Carpenter, E.P., Hawkins, A.R., Frost, J.W., Brown, K.A. Nature (1998) [Pubmed]
  8. ODORANT1 regulates fragrance biosynthesis in petunia flowers. Verdonk, J.C., Haring, M.A., van Tunen, A.J., Schuurink, R.C. Plant Cell (2005) [Pubmed]
  9. A Robot-based platform to measure multiple enzyme activities in Arabidopsis using a set of cycling assays: comparison of changes of enzyme activities and transcript levels during diurnal cycles and in prolonged darkness. Gibon, Y., Blaesing, O.E., Hannemann, J., Carillo, P., Höhne, M., Hendriks, J.H., Palacios, N., Cross, J., Selbig, J., Stitt, M. Plant Cell (2004) [Pubmed]
  10. A small decrease of plastid transketolase activity in antisense tobacco transformants has dramatic effects on photosynthesis and phenylpropanoid metabolism. Henkes, S., Sonnewald, U., Badur, R., Flachmann, R., Stitt, M. Plant Cell (2001) [Pubmed]
  11. Operator mutations of the Escherichia coli aroF gene. Garner, C.C., Herrmann, K.M. J. Biol. Chem. (1985) [Pubmed]
  12. Re-evaluating the role of His-143 in the mechanism of type I dehydroquinase from Escherichia coli using two-dimensional 1H,13C NMR. Leech, A.P., Boetzel, R., McDonald, C., Shrive, A.K., Moore, G.R., Coggins, J.R., Sawyer, L., Kleanthous, C. J. Biol. Chem. (1998) [Pubmed]
  13. Hydroaromatic equilibration during biosynthesis of shikimic acid. Knop, D.R., Draths, K.M., Chandran, S.S., Barker, J.L., von Daeniken, R., Weber, W., Frost, J.W. J. Am. Chem. Soc. (2001) [Pubmed]
  14. Molecular basis for the glyphosate-insensitivity of the reaction of 5-enolpyruvylshikimate 3-phosphate synthase with shikimate. Priestman, M.A., Healy, M.L., Funke, T., Becker, A., Schönbrunn, E. FEBS Lett. (2005) [Pubmed]
  15. Molecular basis for the herbicide resistance of Roundup Ready crops. Funke, T., Han, H., Healy-Fried, M.L., Fischer, M., Schönbrunn, E. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  16. Solute transporters as connecting elements between cytosol and plastid stroma. Weber, A.P. Curr. Opin. Plant Biol. (2004) [Pubmed]
  17. Stabilization of the shikimate pathway enzyme dehydroquinase by covalently bound ligand. Kleanthous, C., Reilly, M., Cooper, A., Kelly, S., Price, N.C., Coggins, J.R. J. Biol. Chem. (1991) [Pubmed]
  18. A new view of the mechanisms of UDP-N-acetylglucosamine enolpyruvyl transferase (MurA) and 5-enolpyruvylshikimate-3-phosphate synthase (AroA) derived from X-ray structures of their tetrahedral reaction intermediate states. Eschenburg, S., Kabsch, W., Healy, M.L., Schonbrunn, E. J. Biol. Chem. (2003) [Pubmed]
  19. Selective overproduction of 5-enol-pyruvylshikimic acid 3-phosphate synthase in a plant cell culture which tolerates high doses of the herbicide glyphosate. Smart, C.C., Johänning, D., Müller, G., Amrhein, N. J. Biol. Chem. (1985) [Pubmed]
  20. Characterization of two functional phosphoenolpyruvate/phosphate translocator (PPT) genes in Arabidopsis--AtPPT1 may be involved in the provision of signals for correct mesophyll development. Knappe, S., Löttgert, T., Schneider, A., Voll, L., Flügge, U.I., Fischer, K. Plant J. (2003) [Pubmed]
  21. The water-soluble extract of Illicium anisatum stimulates mouse vibrissae follicles in organ culture. Sakaguchi, I., Ishimoto, H., Matsuo, M., Ikeda, N., Minamino, M., Kato, Y. Exp. Dermatol. (2004) [Pubmed]
  22. Expression of bacterial chorismate pyruvate-lyase in tobacco: evidence for the presence of chorismate in the plant cytosol. Sommer, S., Heide, L. Plant Cell Physiol. (1998) [Pubmed]
  23. Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism. Hoffmann, L., Maury, S., Martz, F., Geoffroy, P., Legrand, M. J. Biol. Chem. (2003) [Pubmed]
  24. The Arabidopsis phenylalanine insensitive growth mutant exhibits a deregulated amino acid metabolism. Voll, L.M., Allaire, E.E., Fiene, G., Weber, A.P. Plant Physiol. (2004) [Pubmed]
  25. DNA sequence, organization and regulation of the qa gene cluster of Neurospora crassa. Geever, R.F., Huiet, L., Baum, J.A., Tyler, B.M., Patel, V.B., Rutledge, B.J., Case, M.E., Giles, N.H. J. Mol. Biol. (1989) [Pubmed]
  26. Combined transcript and metabolite profiling of Arabidopsis leaves reveals fundamental effects of the thiol-disulfide status on plant metabolism. Kolbe, A., Oliver, S.N., Fernie, A.R., Stitt, M., van Dongen, J.T., Geigenberger, P. Plant Physiol. (2006) [Pubmed]
  27. Global phenotypic analysis and transcriptional profiling defines the weak acid stress response regulon in Saccharomyces cerevisiae. Schüller, C., Mamnun, Y.M., Mollapour, M., Krapf, G., Schuster, M., Bauer, B.E., Piper, P.W., Kuchler, K. Mol. Biol. Cell (2004) [Pubmed]
  28. Expression of the Escherichia coli dam gene. Løbner-Olesen, A., Boye, E., Marinus, M.G. Mol. Microbiol. (1992) [Pubmed]
  29. Cloning and analysis of the shiA gene, which encodes the shikimate transport system of escherichia coli K-12. Whipp, M.J., Camakaris, H., Pittard, A.J. Gene (1998) [Pubmed]
  30. Identification of the gene (aroK) encoding shikimic acid kinase I of Escherichia coli. Løbner-Olesen, A., Marinus, M.G. J. Bacteriol. (1992) [Pubmed]
  31. Cloning of an Arabidopsis thaliana gene encoding 5-enolpyruvylshikimate-3-phosphate synthase: sequence analysis and manipulation to obtain glyphosate-tolerant plants. Klee, H.J., Muskopf, Y.M., Gasser, C.S. Mol. Gen. Genet. (1987) [Pubmed]
  32. Interaction of the herbicide glyphosate with its target enzyme 5-enolpyruvylshikimate 3-phosphate synthase in atomic detail. Schönbrunn, E., Eschenburg, S., Shuttleworth, W.A., Schloss, J.V., Amrhein, N., Evans, J.N., Kabsch, W. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  33. BzdR, a repressor that controls the anaerobic catabolism of benzoate in Azoarcus sp. CIB, is the first member of a new subfamily of transcriptional regulators. Barragán, M.J., Blázquez, B., Zamarro, M.T., Mancheño, J.M., García, J.L., Díaz, E., Carmona, M. J. Biol. Chem. (2005) [Pubmed]
  34. Arabidopsis seed development and germination is associated with temporally distinct metabolic switches. Fait, A., Angelovici, R., Less, H., Ohad, I., Urbanczyk-Wochniak, E., Fernie, A.R., Galili, G. Plant Physiol. (2006) [Pubmed]
  35. The in-vitro synthesized tomato shikimate kinase precursor is enzymatically active and is imported and processed to the mature enzyme by chloroplasts. Schmid, J., Schaller, A., Leibinger, U., Boll, W., Amrhein, N. Plant J. (1992) [Pubmed]
  36. Targeting the shikimate pathway in the malaria parasite Plasmodium falciparum. McConkey, G.A. Antimicrob. Agents Chemother. (1999) [Pubmed]
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