Cinnamoyl-CoA

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:

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.

Enzymes using cinnamoyl-coenzyme A Cinnamoyl-CoA reductase catalyzes the chemical reaction which produces cinnamaldehyde from cinnamoyl-CoA:

The reaction is important in the production of monolignols, which are the building blocks for plant lignin.

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.

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.

References