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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
Chemical Compound Review

Caffeoyl-coa     [5-(6-aminopurin-9-yl)-2- [[[[3-[2-[2-[(E)...

Synonyms: AC1O1EJ3, 53034-79-0, Caffeoyl-coenzyme A, Coenzyme A, caffeoyl-
 
 
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Disease relevance of Caffeoyl-coa

 

High impact information on Caffeoyl-coa

  • Transgenic alfalfa plants were generated harboring caffeic acid 3-O-methyltransferase (COMT) and caffeoyl CoA 3-O-methyltransferase (CCOMT) cDNA sequences under control of the bean phenylalanine ammonia-lyase PAL2 promoter [2].
  • However, functionally, yeast-expressed AEOMT enzyme catalyzed the methylation of CAOMT substrates, caffeic and 5-hydroxyferulic acids, as well as CCoAOMT substrates, caffeoyl CoA and 5-hydroxyferuloyl CoA esters, with similar specific activities and was completely inactive with substrates associated with flavonoid synthesis [3].
  • Cloning and functional expression of the corresponding cDNA verified that the new methyltransferase is a multifunctional 26.6-kDa Mg(2+)-dependent enzyme, which shows a significant sequence similarity to the cluster of caffeoyl coenzyme A-methylating enzymes [4].
  • Besides caffeoyl-CoA and flavonols, a high specificity was also observed for caffeoylglucose, a compound never before reported to be methylated by any plant O-methyltransferase [4].
  • Identification of the enzymatic active site of tobacco caffeoyl-coenzyme A O-methyltransferase by site-directed mutagenesis [5].
 

Biological context of Caffeoyl-coa

 

Associations of Caffeoyl-coa with other chemical compounds

 

Gene context of Caffeoyl-coa

  • The crystallographic structure of rat liver catechol O-methyltransferase was used as a template to construct a homology model for tobacco caffeoyl-coenzyme A O-methyltransferase [5].
  • The ectopic deposition of lignin in the pith of elp1 stems was accompanied by an increase in the activities of enzymes in the lignin biosynthetic pathway and with the ectopic expression of caffeoyl coenzyme A O-methyltransferase in pith cells [13].
 

Analytical, diagnostic and therapeutic context of Caffeoyl-coa

  • Similar changes in circular dichroism spectra were observed after addition of caffeoyl coenzyme A to the wild-type enzyme and the substitution mutants but not in the case of deletion mutants, thus revealing the importance of these sequences in substrate-enzyme interactions [5].
  • The Pt4CL1 product, caffeoyl-CoA, predominated in mixed-substrate assays with xylem extract, and this was consistent with the near absence of Pt4CL2 expression in xylem tissue as determined by in situ hybridization [14].
  • Based on sequence analysis and substrate specificity, the enzyme classifies as a cation-dependent O-methyltransferase with pronounced preference for caffeoyl coenzyme A, when assayed in the presence of Mg2+-ions [15].

References

  1. Isolation, cloning and expression of a multifunctional O-methyltransferase capable of forming 2,5-dimethyl-4-methoxy-3(2H)-furanone, one of the key aroma compounds in strawberry fruits. Wein, M., Lavid, N., Lunkenbein, S., Lewinsohn, E., Schwab, W., Kaldenhoff, R. Plant J. (2002) [Pubmed]
  2. Downregulation of caffeic acid 3-O-methyltransferase and caffeoyl CoA 3-O-methyltransferase in transgenic alfalfa. impacts on lignin structure and implications for the biosynthesis of G and S lignin. Guo, D., Chen, F., Inoue, K., Blount, J.W., Dixon, R.A. Plant Cell (2001) [Pubmed]
  3. A novel multifunctional O-methyltransferase implicated in a dual methylation pathway associated with lignin biosynthesis in loblolly pine. Li, L., Popko, J.L., Zhang, X.H., Osakabe, K., Tsai, C.J., Joshi, C.P., Chiang, V.L. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  4. A novel Mg(2+)-dependent O-methyltransferase in the phenylpropanoid metabolism of Mesembryanthemum crystallinum. Ibdah, M., Zhang, X.H., Schmidt, J., Vogt, T. J. Biol. Chem. (2003) [Pubmed]
  5. Identification of the enzymatic active site of tobacco caffeoyl-coenzyme A O-methyltransferase by site-directed mutagenesis. Hoffmann, L., Maury, S., Bergdoll, M., Thion, L., Erard, M., Legrand, M. J. Biol. Chem. (2001) [Pubmed]
  6. Modifications in lignin and accumulation of phenolic glucosides in poplar xylem upon down-regulation of caffeoyl-coenzyme A O-methyltransferase, an enzyme involved in lignin biosynthesis. Meyermans, H., Morreel, K., Lapierre, C., Pollet, B., De Bruyn, A., Busson, R., Herdewijn, P., Devreese, B., Van Beeumen, J., Marita, J.M., Ralph, J., Chen, C., Burggraeve, B., Van Montagu, M., Messens, E., Boerjan, W. J. Biol. Chem. (2000) [Pubmed]
  7. Molecular cloning, induction and taxonomic distribution of caffeoyl-CoA 3-O-methyltransferase, an enzyme involved in disease resistance. Schmitt, D., Pakusch, A.E., Matern, U. J. Biol. Chem. (1991) [Pubmed]
  8. Tobacco O-methyltransferases involved in phenylpropanoid metabolism. The different caffeoyl-coenzyme A/5-hydroxyferuloyl-coenzyme A 3/5-O-methyltransferase and caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase classes have distinct substrate specificities and expression patterns. Maury, S., Geoffroy, P., Legrand, M. Plant Physiol. (1999) [Pubmed]
  9. Nucleotide sequence of a cDNA clone encoding caffeoyl-coenzyme A 3-O-methyltransferase of Stellaria longipes (Caryophyllaceae). Zhang, X.H., Dickson, E.E., Chinnappa, C.C. Plant Physiol. (1995) [Pubmed]
  10. Molecular cloning and functional expression of a stress-induced multifunctional O-methyltransferase with pinosylvin methyltransferase activity from Scots pine (Pinus sylvestris L.). Chiron, H., Drouet, A., Claudot, A.C., Eckerskorn, C., Trost, M., Heller, W., Ernst, D., Sandermann, H. Plant Mol. Biol. (2000) [Pubmed]
  11. Genetic mapping of a caffeoyl-coenzyme A 3-O-methyltransferase gene in coffee trees. Impact on chlorogenic acid content. Campa, C., Noirot, M., Bourgeois, M., Pervent, M., Ky, C.L., Chrestin, H., Hamon, S., de Kochko, A. Theor. Appl. Genet. (2003) [Pubmed]
  12. Specificities of functionally expressed chalcone and acridone synthases from Ruta graveolens. Springob, K., Lukacin, R., Ernwein, C., Gröning, I., Matern, U. Eur. J. Biochem. (2000) [Pubmed]
  13. Ectopic deposition of lignin in the pith of stems of two Arabidopsis mutants. Zhong, R., Ripperger, A., Ye, Z.H. Plant Physiol. (2000) [Pubmed]
  14. Differential substrate inhibition couples kinetically distinct 4-coumarate:coenzyme a ligases with spatially distinct metabolic roles in quaking aspen. Harding, S.A., Leshkevich, J., Chiang, V.L., Tsai, C.J. Plant Physiol. (2002) [Pubmed]
  15. Cations modulate the substrate specificity of bifunctional class I O-methyltransferase from Ammi majus. Lukacin, R., Matern, U., Specker, S., Vogt, T. FEBS Lett. (2004) [Pubmed]
 
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