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|
Expected Taxonomic Range: Viridiplantae
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 [Strack87c]. 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].
Strack87c: 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
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
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.
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
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
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