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discounted EARLY registration ends Dec 31, 2014
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MetaCyc Enzyme: cinnamoyl-CoA lyase / cinnamoyl-CoA hydratase

Species: Hypericum androsaemum

Summary:
This enzyme activity could be detected in desalted cell free extracts in the absence of NAD+ and CoA. Although the identities of the final end products, acetyl-CoA and benzaldehyde were confirmed, the intermediate product, 3-hydroxy-3-phenylpropanoyl-CoA was never recovered leading the researchers to suggest that a single bi-functional enzyme catalyzes two sequential reactions [Abd02]. There is some precedent for the existence of a similar dual activity enzyme, feruloyl-CoA hydratase / lyase in Pseudomonas fluorescens [Gasson98, Narbad98].

Further ammonium sulfate fractionation led to an enrichment of the cinnamoyl-CoA hydratase/lyase activity in the 40-50% fraction [Abd02]. This partially purified enzyme had the highlest level of activity with cinnamoyl-CoA, minor activity (33%) with 3-coumaroyl-CoA, and no activity with 4-coumaryl-CoA or 2-coumaroyl-CoA in vitro [Abd02].

The activity of this enzyme in cell cultures appears to be up-regulated by methyl jasmonate. This plant signaling defense compound also stimulates the activity of several other enzymes in the benzoate biosynthesis III (CoA-dependent, non-β-oxidative) pathway, and precedes a rise in the production of xanthones, a class of secondary metabolites made in Hypericum androsaemum [Abd02].

Gene-Reaction Schematic: ?

Credits:
Created 16-Mar-2010 by Dreher KA , TAIR


Enzymatic reaction of: cinnamoyl-CoA lyase

Synonyms: cinnamoyl-coenzyme A lyase

3-hydroxy-3-phenylpropanoyl-CoA <=> benzaldehyde + acetyl-CoA

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is favored in the direction shown.

In Pathways: benzoate biosynthesis III (CoA-dependent, non-β-oxidative)

T(opt): 30 °C [Abd02]

pH(opt): 7 [Abd02]


Enzymatic reaction of: cinnamoyl-CoA hydratase

Synonyms: cinnamoyl-coenzyme A hydratase

(E)-cinnamoyl-CoA + H2O <=> 3-hydroxy-3-phenylpropanoyl-CoA

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is favored in the direction shown.

In Pathways: benzoate biosynthesis III (CoA-dependent, non-β-oxidative) , benzoyl-CoA biosynthesis


References

Abd02: Abd El-Mawla AM, Beerhues L (2002). "Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum." Planta 214(5);727-33. PMID: 11882941

Gasson98: Gasson MJ, Kitamura Y, McLauchlan WR, Narbad A, Parr AJ, Parsons EL, Payne J, Rhodes MJ, Walton NJ (1998). "Metabolism of ferulic acid to vanillin. A bacterial gene of the enoyl-SCoA hydratase/isomerase superfamily encodes an enzyme for the hydration and cleavage of a hydroxycinnamic acid SCoA thioester." J Biol Chem 273(7);4163-70. PMID: 9461612

Narbad98: Narbad A, Gasson MJ (1998). "Metabolism of ferulic acid via vanillin using a novel CoA-dependent pathway in a newly-isolated strain of Pseudomonas fluorescens." Microbiology 144 ( Pt 5);1397-405. PMID: 9611814


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 Sun Nov 23, 2014, BIOCYC14A.