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.
Synonyms: (E)-cinnamoyl-CoA biosynthesis, trans-cinnamoyl-coenzyme A biosynthesis, cinnamoyl-CoA biosynthesis
|Superclasses:||Biosynthesis → Aromatic Compounds Biosynthesis|
|Biosynthesis → Secondary Metabolites Biosynthesis → Phenylpropanoid Derivatives Biosynthesis → Cinnamates Biosynthesis|
Some taxa known to possess this pathway include : Arabidopsis thaliana col, Catharanthus roseus, Cucumis sativus, Hypericum androsaemum, Hypericum calycinum, Nicotiana tabacum, Petunia x hybrida, Streptomyces maritimus
(E)-cinnamoyl-CoA and the closely related compound, 4-coumaryl-CoA are important precursors to a number of compound classes, including phenylpropanoids, flavonoids, and volatile benzenoids in plants and polyketides in plants and bacteria [Moore02, Katsuyama09]. Members of these classes can play many roles, for instance as defense, signaling, pigment, and aroma compounds.
About This Pathway
Both (E)-cinnamoyl-CoA and 4-coumaryl-CoA are derived from trans-cinnamate produced from L-phenylalanine by the activity of a phenylalanine ammonia lysase (PAL). Their only structural difference is the presence of a hydroxyl group in the 4-position on the benzene ring. If the hydroxyl group is added directly to trans-cinnamate, then 4-coumaryl-CoA can be made without a (E)-cinnamoyl-CoA intermediate (see phenylpropanoid biosynthesis, initial reactions and phenylpropanoid biosynthesis). However, as shown in this pathway, trans-cinnamate can be also be a direct substrate for a CoA ligase. In some cases, the (E)-cinnamoyl-CoA generated by this enzyme may be used directly in secondary metabolic pathways (e.g. benzoate biosynthesis I (CoA-dependent, β-oxidative), pinobanksin biosynthesis), however, it may also be used to produce 4-coumaryl-CoA through a late hydroxylation (e.g. curcuminoid biosynthesis).
Although PAL has been well-characterized in plants since its initial discovery in 1961 [Koukol61], it wasn't until much later than an enzyme believed to be responsible for catalyzing the second step in this pathway was first identified in bacteria [Moore02].
In plants, the first step in this pathway is often rate limiting, for example, in the production of flavonoids. Therefore, expression levels and activity levels of PAL are often highly regulated and changes are induced by different stresses (rev. in [MacDonald07], ex. in [Liu06]).
Unification Links: PlantCyc:PWY-6457
Guranowski10: Guranowski A, Wojdyla AM, Zimny J, Wypijewska A, Kowalska J, Jemielity J, Davis RE, Bieganowski P (2010). "Dual activity of certain HIT-proteins: A. thaliana Hint4 and C. elegans DcpS act on adenosine 5'-phosphosulfate as hydrolases (forming AMP) and as phosphorylases (forming ADP)." FEBS Lett 584(1);93-8. PMID: 19896942
Koukol61: Koukol, J., Conn, E.E. (1961). "The metabolism of aromatic compounds in higher plants. IV. Purification and properties of the phenylalanine deaminase of Hordeum vulgare." J Biol Chem 236;2692-8. PMID: 14458851
Liu06: Liu R, Xu S, Li J, Hu Y, Lin Z (2006). "Expression profile of a PAL gene from Astragalus membranaceus var. Mongholicus and its crucial role in flux into flavonoid biosynthesis." Plant Cell Rep 25(7);705-10. PMID: 16456646
Moore02: Moore BS, Hertweck C, Hopke JN, Izumikawa M, Kalaitzis JA, Nilsen G, O'Hare T, Piel J, Shipley PR, Xiang L, Austin MB, Noel JP (2002). "Plant-like biosynthetic pathways in bacteria: from benzoic acid to chalcone." J Nat Prod 65(12);1956-62. PMID: 12502351
Xiang02: Xiang L, Moore BS (2002). "Inactivation, complementation, and heterologous expression of encP, a novel bacterial phenylalanine ammonia-lyase gene." J Biol Chem 277(36);32505-9. PMID: 12082112
Xiang03: Xiang L, Moore BS (2003). "Characterization of benzoyl coenzyme A biosynthesis genes in the enterocin-producing bacterium "Streptomyces maritimus"." J Bacteriol 185(2);399-404. PMID: 12511484
Colquhoun12: Colquhoun TA, Marciniak DM, Wedde AE, Kim JY, Schwieterman ML, Levin LA, Van Moerkercke A, Schuurink RC, Clark DG (2012). "A peroxisomally localized acyl-activating enzyme is required for volatile benzenoid formation in a Petuniaxhybrida cv. 'Mitchell Diploid' flower." J Exp Bot 63(13);4821-33. PMID: 22771854
Gaid12: Gaid MM, Sircar D, Muller A, Beuerle T, Liu B, Ernst L, Hansch R, Beerhues L (2012). "Cinnamate:CoA Ligase Initiates the Biosynthesis of a Benzoate-Derived Xanthone Phytoalexin in Hypericum calycinum Cell Cultures." Plant Physiol 160(3);1267-80. PMID: 22992510
Hertweck01: Hertweck C, Jarvis AP, Xiang L, Moore BS, Oldham NJ (2001). "A mechanism of benzoic acid biosynthesis in plants and bacteria that mirrors fatty acid beta-oxidation." Chembiochem 2(10);784-6. PMID: 11948863
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
Piel00: Piel J, Hertweck C, Shipley PR, Hunt DM, Newman MS, Moore BS (2000). "Cloning, sequencing and analysis of the enterocin biosynthesis gene cluster from the marine isolate 'Streptomyces maritimus': evidence for the derailment of an aromatic polyketide synthase." Chem Biol 7(12);943-55. PMID: 11137817
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
Van09: Van Moerkercke A, Schauvinhold I, Pichersky E, Haring MA, Schuurink RC (2009). "A plant thiolase involved in benzoic acid biosynthesis and volatile benzenoid production." Plant J 60(2);292-302. PMID: 19659733
Vannelli07: Vannelli T, Wei Qi W, Sweigard J, Gatenby AA, Sariaslani FS (2007). "Production of p-hydroxycinnamic acid from glucose in Saccharomyces cerevisiae and Escherichia coli by expression of heterologous genes from plants and fungi." Metab Eng 9(2);142-51. PMID: 17204442
Xue07: Xue Z, McCluskey M, Cantera K, Sariaslani FS, Huang L (2007). "Identification, characterization and functional expression of a tyrosine ammonia-lyase and its mutants from the photosynthetic bacterium Rhodobacter sphaeroides." J Ind Microbiol Biotechnol 34(9);599-604. PMID: 17602252
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