Information on EC 1.14.11.19 - leucocyanidin oxygenase

for references in articles please use BRENDA:EC1.14.11.19
Word Map on EC 1.14.11.19
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:

The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.11.19
-
RECOMMENDED NAME
GeneOntology No.
leucocyanidin oxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a (2R,3S,4S)-leucoanthocyanidin + 2-oxoglutarate + O2 = a (4S)- 2,3-dehydroflavan-3,4-diol + succinate + CO2 + H2O
show the reaction diagram
(1a)
-
-
-
a (2R,3S,4S)-leucoanthocyanidin + 2-oxoglutarate + O2 = an anthocyanidin + succinate + CO2 + 2 H2O
show the reaction diagram
a (4S)- 2,3-dehydroflavan-3,4-diol = an anthocyanidin + H2O
show the reaction diagram
(1b)
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Flavonoid biosynthesis
-
-
Metabolic pathways
-
-
Biosynthesis of secondary metabolites
-
-
proanthocyanidins biosynthesis from flavanols
-
-
anthocyanin biosynthesis
-
-
anthocyanin biosynthesis (pelargonidin 3-O-glucoside)
-
-
SYSTEMATIC NAME
IUBMB Comments
leucocyanidin,2-oxoglutarate:oxygen oxidoreductase
The enzyme requires Fe(II) and ascorbate. It is involved in the pathway by which many flowering plants make anthocyanin flower pigments (glycosylated anthocyandins). The enzyme hydroxylates the C-3 carbon, followed by a trans diaxial elimination, forming a C-2,C-3 enol. The product loses a second water molecule to form anthocyanidins. When assayed in vitro, non-enzymic epimerization of the product can lead to formation of dihydroflavanols. Thus when the substrate is leucocyanidin, a mixture of (+)-taxifolin and (+)-epitaxifolin are formed. The enzyme can also oxidize the formed (+)-taxifolin to quercetin (cf. EC 1.14.11.23, flavonol synthase) [2,3].
CAS REGISTRY NUMBER
COMMENTARY hide
180984-01-4
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
snapdragon
-
-
Manually annotated by BRENDA team
yellow- and black-seeded accessions, gene BjANS
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
1 year old seedlings and 12 year old grafts
UniProt
Manually annotated by BRENDA team
Lam cultivar A5, A1, Yamakawamurasaki, and A3 and one of white-fleshed sweet potato cultivar Yubeibai
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
overexpression in rice mutant Nootripathu, which accumulates proanthocyanidins exclusively in pericarp
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
maize
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
lack of enzyme encoding gene BjANS expression blocks biosynthesis of proanthocyanidins in the yellow seed coat, and therefore seeds appear yellow because of transparent testa
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2R,3R)-trans-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + O2
show the reaction diagram
-
-
-
-
?
(2R,3S,4R)-trans-leucocyanidin + 2-oxoglutarate + O2
trans-dihydroquercetin + cis-dihydroquercetin + quercetin + succinate + CO2
show the reaction diagram
-
-
-
-
?
(2R,3S,4S)-cis-leucocyanidin + 2-oxoglutarate + O2
quercetin + succinate + CO2
show the reaction diagram
-
-
-
-
?
2R,3S,4R-trans-leucocyanidin + 2-oxoglutarate + O2
2R,3S-cis-dihydroquercetin + 2R,3R-trans-dihydroquercetin + cyanidin + quercetin
show the reaction diagram
-
-
55% 2R,3S-cis-dihydroquercetin + 11% 2R,3R-trans-dihydroquercetin + 4% cyanidin + 30% quercetin
-
?
2R,3S,4S-cis-leucoanthocyanidin + 2-oxoglutarate + O2
cis- and trans-dihydroquercetins + succinate + CO2 + 2 H2O
show the reaction diagram
-
catalyses the penultimate step in anthocyanin biosynthesis by oxidation of the 2R,3S,4S-cis-leucoanthocyanidins
both quercetin and dihydroquercetin are products with the distribution being dependent on the C-4 stereochemistry of the leucocyanidin substrates
-
?
2R,3S,4S-cis-leucocyanidin + 2-oxoglutarate + O2
2R,3S-cis-dihydroquercetin + 2R,3R-trans-dihydroquercetin + cyanidin + quercetin
show the reaction diagram
-
-
10% 2R,3S-cis-dihydroquercetin + 2% 2R,3R-trans-dihydroquercetin + 3% cyanidin + 85% quercetin
-
?
3,4-cis-leucocyanidin + 2-oxoglutarate + O2
cyanidin + succinate + CO2
show the reaction diagram
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2
show the reaction diagram
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + O2
show the reaction diagram
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
show the reaction diagram
leucocyanidin + 2-oxoglutarate + O2 + H+
cyanidin + succinate + CO2 + 2 H2O
show the reaction diagram
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + O2
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2R,3S,4S-cis-leucoanthocyanidin + 2-oxoglutarate + O2
cis- and trans-dihydroquercetins + succinate + CO2 + 2 H2O
show the reaction diagram
-
catalyses the penultimate step in anthocyanin biosynthesis by oxidation of the 2R,3S,4S-cis-leucoanthocyanidins
both quercetin and dihydroquercetin are products with the distribution being dependent on the C-4 stereochemistry of the leucocyanidin substrates
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Iron
Fe2+ is required
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-oxoglutarate
ascorbate
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.038
(2R,3S,4R)-leucocyanidin
-
-
0.059
2-oxoglutarate
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
-
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.18
sequence calculation
5.27
-
calculated from sequence
6.2
calculated
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
all lines and seed coats of the black-seeded lines, not in the yellow-seeded seed coats
Manually annotated by BRENDA team
young and mature. Weakly expressed in young fruits, highest level of GbANS mRNA is observed in mature fruits
Manually annotated by BRENDA team
-
exposure of shaded swollen hypocotyls to artificial light sources. Only UV-A light induces anthocyanin biosynthesis. During 24 h of exposure, expression of anthocyanidin synthase increases together with phenylalanine ammonia lyase EC 4.3.1.5, chalcone synthase EC 2.3.1.74, flavanone 3-hydroxylase EC 1.14.11.9, and dihydroflavonol 4-reductase EC 1.1.1.219
Manually annotated by BRENDA team
-
primarily distributed in the growth point and leaf primordium of the leaf buds
Manually annotated by BRENDA team
moderate expression level
Manually annotated by BRENDA team
-
fibrous, thick, and storage roots. IbANS is expressed most abundantly during the formation of storage roots
Manually annotated by BRENDA team
levels of transcripts encoding anthocyanidin synthase, dihydroflavonol reductase and anthocyanidin reductase parallel the accumulation of proanthocyanidins in developing seeds
Manually annotated by BRENDA team
BjANS expressed in the seed coats of the black-seeded lines and in embryos of the all lines, but not in the yellow-seeded seed coats, RT-PCR expression analysis
Manually annotated by BRENDA team
-
perilla, red or green
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40300
x * 40300, calculated
40450
-
calculated
40862
x * 40862, sequence calculation
41000
x * 41000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
affinity chromatography
of recombinant enzyme
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
analysis of expression in wheat-rye hybrids
expressed in Escherichia coli
expressed in Escherichia coli strain DH5alpha
-
expression in Escherichia coli JM109
expression in Escherichia coli, overexpression in rice mutant Nootripathu, which accumulates proanthocyanidins exclusively in pericarp
gene BjANS, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree
overexpression in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
decrease at stage of flowering
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
-
basis work for molecular directional breeding of sweet potato
additional information