KEGG   ENZYME: 1.14.11.62Help
Entry
EC 1.14.11.62               Enzyme                                 

Name
trans-4-coumaroyl-CoA 2-hydroxylase;
Diox4 (gene name);
C2'H (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor
BRITE hierarchy
Sysname
(2E)-3-(4-hydroxyphenyl)prop-2-enoyl-CoA,2-oxoglutarate:oxygen oxidoreductase (2-hydroxylating)
Reaction(IUBMB)
trans-4-coumaroyl-CoA + 2-oxoglutarate + O2 = 2,4-dihydroxycinnamoyl-CoA + succinate + CO2 [RN:R12306]
Reaction(KEGG)
Substrate
trans-4-coumaroyl-CoA [CPD:C00223];
2-oxoglutarate [CPD:C00026];
O2 [CPD:C00007]
Product
2,4-dihydroxycinnamoyl-CoA [CPD:C22070];
succinate [CPD:C00042];
CO2 [CPD:C00011]
Comment
Requires iron(II) and ascorbate. The product spontaneously undergoes trans-cis isomerization followed by lactonization and cyclization, liberating CoA and forming umbelliferone. The enzymes from the plants Ruta graveolens and Ipomoea batatas also act on trans-feruloyl-CoA (cf. EC 1.14.11.61, feruloyl-CoA 6-hydroxylase).
History
EC 1.14.11.62 created 2019
Pathway
ec00940  Phenylpropanoid biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K23378  trans-4-coumaroyl-CoA 2-hydroxylase
Genes
CIT: 102611531 102611821 102612308
CIC: CICLE_v10015700mg CICLE_v10017914mg CICLE_v10018343mg CICLE_v10029948mg
INI: 109160283 109160284 109160285 109160336
Taxonomy
Reference
1  [PMID:22168819]
  Authors
Vialart G, Hehn A, Olry A, Ito K, Krieger C, Larbat R, Paris C, Shimizu B, Sugimoto Y, Mizutani M, Bourgaud F
  Title
A 2-oxoglutarate-dependent dioxygenase from Ruta graveolens L. exhibits p-coumaroyl CoA 2'-hydroxylase activity (C2'H): a missing step in the synthesis of umbelliferone in plants.
  Journal
Plant J 70:460-70 (2012)
DOI:10.1111/j.1365-313X.2011.04879.x
Reference
2  [PMID:22169019]
  Authors
Matsumoto S, Mizutani M, Sakata K, Shimizu B
  Title
Molecular cloning and functional analysis of the ortho-hydroxylases of p-coumaroyl coenzyme A/feruloyl coenzyme A involved in formation of umbelliferone and scopoletin in sweet potato, Ipomoea batatas (L.) Lam.
  Journal
Phytochemistry 74:49-57 (2012)
DOI:10.1016/j.phytochem.2011.11.009
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.11.62
IUBMB Enzyme Nomenclature: 1.14.11.62
ExPASy - ENZYME nomenclature database: 1.14.11.62
BRENDA, the Enzyme Database: 1.14.11.62

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