Chemistry:Cinnamoyl-CoA
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| IUPAC name
3′-O-Phosphonoadenosine 5′-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-3-phenylprop-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl dihydroxen diphosphate]
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| Systematic IUPAC name
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl (3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-3-phenylprop-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl dihydrogen diphosphate | |
| Other names
Cinnamoyl-coa
(E)-cinnamoyl-CoA Coenzyme A, S-(3-phenyl-2-propenoate) (E)-benzylideneacetyl-CoA 3-phenylacryloyl-CoA | |
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3D model (JSmol)
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| Properties | |
| C30H42N7O17P3S | |
| Molar mass | 897.68 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Cinnamoyl-coenzyme A is an intermediate in the phenylpropanoid metabolic pathway. It is the thioester formed between cinnamic acid and coenzyme A.
Biosynthesis
Cinnamoyl-CoA is produced in two enzymatically-catalysed steps of the phenylpropanoid metabolic pathway. In the first, phenylalanine ammonia-lyase (PAL), converts the amino acid phenylalanine to cinnamic acid:[1]
- REDIRECT Template:Chemical reaction
Subsequently, 4-coumarate-CoA ligase produces the thioester with coenzyme A. The reaction is driven to completion by the energy produced by the hydrolysis of adenosine triphosphate (ATP) to its monophosphate AMP, releasing diphosphate.[2]
- REDIRECT Template:Chemical reaction
Enzymes using cinnamoyl-coenzyme A
Cinnamoyl-CoA reductase catalyzes the chemical reaction which produces cinnamaldehyde from cinnamoyl-CoA:[3]
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The reaction is important in the production of monolignols, which are the building blocks for plant lignin.[4]
Pinosylvin synthase combines one unit of cinnamoyl-CoA with three of malonyl-CoA to form the stilbene, pinosylvin, with coenzyme A and carbon dioxide as byproducts. The product is produced in response to fungal attack on the pine tree Pinus sylvestris.[5][6]
- REDIRECT Template:Chemical reaction
Biology:Cinnamoyl-CoA:phenyllactate CoA-transferase catalyzes a chemical reaction which transfers the coenzyme A thioester from cinnamoyl-CoA to (R)-phenyllactic acid, giving (R)-phenyllactyl-CoA and cinnamic acid.[7]
References
- ↑ "Structural and catalytic properties of the four phenylalanine ammonia-lyase isoenzymes from parsley (Petroselinum crispum Nym.)". European Journal of Biochemistry 225 (1): 491–9. October 1994. doi:10.1111/j.1432-1033.1994.00491.x. PMID 7925471.
- ↑ "Isolation and properties of hydroxycinnamate: CoA ligase from lignifying tissue of Forsythia". Eur. J. Biochem. 42 (2): 453–9. 1974. doi:10.1111/j.1432-1033.1974.tb03359.x. PMID 4364250.
- ↑ "Structural studies of cinnamoyl-CoA reductase and cinnamyl-alcohol dehydrogenase, key enzymes of monolignol biosynthesis". The Plant Cell 26 (9): 3709–27. September 2014. doi:10.1105/tpc.114.127399. PMID 25217505. Bibcode: 2014PlanC..26.3709P.
- ↑ "Two cinnamoyl-CoA reductase (CCR) genes from Arabidopsis thaliana are differentially expressed during development and in response to infection with pathogenic bacteria". Phytochemistry 57 (7): 1187–95. August 2001. doi:10.1016/s0031-9422(01)00053-x. PMID 11430991. Bibcode: 2001PChem..57.1187L.
- ↑ "Stilbene Synthase from Seedlings of Pinus sylvestris : Purification and Induction in Response to Fungal Infection". Molecular Plant-Microbe Interactions 3 (6): 444. 1990. doi:10.1094/MPMI-3-444. Bibcode: 1990MPMI....3..444G. http://www.apsnet.org/publications/mpmi/backissues/Documents/1990Abstracts/Microbe03-444.htm.
- ↑ "Impact of Environmental Factors on Stilbene Biosynthesis". Plants 10 (1): 90. January 2021. doi:10.3390/plants10010090. PMID 33406721. Bibcode: 2021Plnts..10...90V.
- ↑ "The involvement of coenzyme A esters in the dehydration of (R)-phenyllactate to (E)-cinnamate by Clostridium sporogenes". Eur. J. Biochem. 267 (12): 3874–84. 2000. doi:10.1046/j.1432-1327.2000.01427.x. PMID 10849007.
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