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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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MetaCyc Pathway: caffeoylglucarate biosynthesis

Enzyme View:

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: Biosynthesis Secondary Metabolites Biosynthesis Phenylpropanoid Derivatives Biosynthesis

Some taxa known to possess this pathway include ? : Nicotiana tabacum , Solanum lycopersicum , Solanum tuberosum

Expected Taxonomic Range: Viridiplantae

Summary:
In Solanum lycopersicum cotyledons, the major intermediates of phenylpropanoid metabolism are chlorogenic acid and 2-O-caffeoylglucarate. In quantitative analysis these two compounds appear to be in a precursor-product relation. Protein extracts of tomato cotyledons were able to catalyze the formation of caffeoylglucaric acid when chlorogenic acid was supplied as the acyl donor [Strack87]. Glucaric acid is the oxidation product of glucose and 2-O-caffeoylglucarate is the acylated product.

The biosynthesis of the hydrocinnamic acid esters has for long been thought be similar to the caffeic acid ester, the chlorogenic acid. Alternate routes of enzymic synthesis are being pursued such as the possibility of chlorogenic acid acting as an acyl donor molecule for caffeoyltransferases [Strack90].

Leaves of Solanum lycopersicum plants accumulate caffeate esters with quinate, glucarate and galactarate. These esters are formed by the action of three enzymes; caffeate CoA ligase, caffeoyl-CoA quinate caffeoyltransferase and chlorogenate-glucarate caffeoyltransferase as shown in the above pathway [Teutschbein10].

Credits:
Created 10-Dec-2010 by Pujar A , Boyce Thompson Institute


References

Strack87: Strack D, Gross W, Wray V, Grotjahn L (1987). "Enzymic synthesis of caffeoylglucaric Acid from chlorogenic Acid and glucaric Acid by a protein preparation from tomato cotyledons." Plant Physiol 83(3);475-8. PMID: 16665274

Strack90: Strack D, Gross W (1990). "Properties and Activity Changes of Chlorogenic Acid:Glucaric Acid Caffeoyltransferase From Tomato (Lycopersicon esculentum)." Plant Physiol 92(1);41-7. PMID: 16667263

Teutschbein10: Teutschbein J, Gross W, Nimtz M, Milkowski C, Hause B, Strack D (2010). "Identification and Localization of a Lipase-like Acyltransferase in Phenylpropanoid Metabolism of Tomato (Solanum lycopersicum)." J Biol Chem 285(49);38374-81. PMID: 20880851

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Boerjan03: Boerjan W, Ralph J, Baucher M (2003). "Lignin biosynthesis." Annu Rev Plant Biol 54;519-46. PMID: 14503002

Ehlting99: Ehlting J, Buttner D, Wang Q, Douglas CJ, Somssich IE, Kombrink E (1999). "Three 4-coumarate:coenzyme A ligases in Arabidopsis thaliana represent two evolutionarily divergent classes in angiosperms." Plant J 1999;19(1);9-20. PMID: 10417722

Hoffmann03: Hoffmann L, Maury S, Martz F, Geoffroy P, Legrand M (2003). "Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism." J Biol Chem 278(1);95-103. PMID: 12381722

Hoffmann04: Hoffmann L, Besseau S, Geoffroy P, Ritzenthaler C, Meyer D, Lapierre C, Pollet B, Legrand M (2004). "Silencing of hydroxycinnamoyl-coenzyme A shikimate/quinate hydroxycinnamoyltransferase affects phenylpropanoid biosynthesis." Plant Cell 16(6);1446-65. PMID: 15161961

Klempien12: Klempien A, Kaminaga Y, Qualley A, Nagegowda DA, Widhalm JR, Orlova I, Shasany AK, Taguchi G, Kish CM, Cooper BR, D'Auria JC, Rhodes D, Pichersky E, Dudareva N (2012). "Contribution of CoA ligases to benzenoid biosynthesis in petunia flowers." Plant Cell 24(5);2015-30. PMID: 22649270

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lepelley07: Lepelley, M, Simkina, A, Cheminadea, G, Cailleta, V, Tremillon, N, McCarthy, J (2007). "Chlorogenic acid synthesis in coffee: An analysis of CGA content and real-time RT-PCR expression of HCT, HQT, C3H1, and CCoAOMT1 genes during grain development in C. canephora." Plant Science, 172, 978-996.

Lin13a: Lin Y, Sun X, Yuan Q, Yan Y (2013). "Combinatorial biosynthesis of plant-specific coumarins in bacteria." Metab Eng 18;69-77. PMID: 23644174

Masai02: Masai E, Harada K, Peng X, Kitayama H, Katayama Y, Fukuda M (2002). "Cloning and characterization of the ferulic acid catabolic genes of Sphingomonas paucimobilis SYK-6." Appl Environ Microbiol 68(9);4416-24. PMID: 12200295

Niggeweg04: Niggeweg R, Michael AJ, Martin C (2004). "Engineering plants with increased levels of the antioxidant chlorogenic acid." Nat Biotechnol 22(6);746-54. PMID: 15107863

Rhodes: Rhodes, M.J.C, Wooltorton, L.S.C "The enzymic conversion of hydroxycinnamic acids to p-coumarylquinic and chlorogenic acids in tomato fruits." Phytochemistry, 15, pg 947.

Rommens08: Rommens CM, Richael CM, Yan H, Navarre DA, Ye J, Krucker M, Swords K (2008). "Engineered native pathways for high kaempferol and caffeoylquinate production in potato." Plant Biotechnol J 6(9);870-86. PMID: 18662373

Rubio06: Rubio S, Larson TR, Gonzalez-Guzman M, Alejandro S, Graham IA, Serrano R, Rodriguez PL (2006). "An Arabidopsis mutant impaired in coenzyme A biosynthesis is sugar dependent for seedling establishment." Plant Physiol 140(3);830-43. PMID: 16415216


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Mon Dec 22, 2014, biocyc13.