Information on EC 1.14.11.19 - leucocyanidin oxygenase

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The expected taxonomic range for this enzyme is: Spermatophyta

EC NUMBER
COMMENTARY
1.14.11.19
-
RECOMMENDED NAME
GeneOntology No.
leucocyanidin oxygenase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
leucocyanidin + 2-oxoglutarate + O2 = cis- and trans-dihydroquercetins + succinate + CO2 + 2 H2O
show the reaction diagram
mechanism
-
leucocyanidin + 2-oxoglutarate + O2 = cis- and trans-dihydroquercetins + succinate + CO2 + 2 H2O
show the reaction diagram
mechanism
-
leucocyanidin + 2-oxoglutarate + O2 = cis- and trans-dihydroquercetins + succinate + CO2 + 2 H2O
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
anthocyanin biosynthesis (cyanidin 3-O-glucoside)
-
Biosynthesis of secondary metabolites
-
Flavonoid biosynthesis
-
Metabolic pathways
-
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 (glycosylated anthocyandin) flower pigments. The intermediates are transformed into cis- and trans-dihydroquercetin [2], which the enzyme can also oxidize to quercetin. Acidification of the products gives anthocyanidin [1], which, however, may not be a natural precursor of the anthocyanins.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
ANS
Q84V01
-
ANS
B2M0X8
-
ANS
-
2-oxoglutarate (2OG) iron-dependent oxygenase
ANS
C7S854
-
ANS
Vitis vinifera Cabernet Sauvignon
-
-
-
anthocyanidin synthase
-
-
anthocyanidin synthase
B2M0X8
-
anthocyanidin synthase
-
-
anthocyanidin synthase
P51091
-
anthocyanidin synthase
A9ZMJ5
-
anthocyanidin synthase
C7S854
-
anthocyanidin synthase
-
-
anthocyanidin synthase
Vitis vinifera Cabernet Sauvignon
-
-
-
anthocyanidine synthase
Q84V01
-
anthocyanin synthase
-
-
-
-
GbANS
B2M0X8
bifunctional enzyme within the anthocyanidin and flavonol biosynthetic pathway
leucoanthocyanidin dioxygenase
-
-
leucoanthocyanidin oxygenase
B2M0X8
2-oxoglutarate iron-dependent oxygenase
leucocyanidin dioxygenase
-
-
-
-
MdANS
P51091
-
CAS REGISTRY NUMBER
COMMENTARY
180984-01-4
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
snapdragon
-
-
Manually annotated by BRENDA team
fls1, EC 1.14.11.23, null mutant
-
-
Manually annotated by BRENDA team
wild-type and ldox/fls1-2 double mutant, lacking leucoanthocyanidin dioxygenase and functional flavonol synthase 1-2, EC 1.14.11.23
-
-
Manually annotated by BRENDA team
yellow- and black-seeded accessions, gene BjANS
UniProt
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
shoot cultures from TNR 31-35 (hybrid of Malus sieversii var. sieversii f. niedzwetzkyana)
UniProt
Manually annotated by BRENDA team
overexpression in rice mutant Nootripathu, which accumulates proanthocyanidins exclusively in pericarp
UniProt
Manually annotated by BRENDA team
Vitis vinifera Cabernet Sauvignon
-
-
-
Manually annotated by BRENDA team
maize
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
malfunction
Q84V01
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
A9ZMJ5
part of flavonoid biosynthetic pathway
metabolism
-
anthocyanidin synthase is one of the key enzymes in the biosynthesis of both anthocyanins and proanthocyanidins in grapevine
metabolism
Q84V01
anthocyanidin synthase, a 2-oxoglutarate iron-dependent oxygenase, converts leucoanthocyanidins into 3-hydroxyanthocyanidin in late flavonoid biosynthesis
metabolism
Vitis vinifera Cabernet Sauvignon
-
anthocyanidin synthase is one of the key enzymes in the biosynthesis of both anthocyanins and proanthocyanidins in grapevine
-
physiological function
-
flavonol synthase activity, correspondending to EC 1.14.11.23, in case of mutants lacking the active flavonol synthase 1
physiological function
-
flavonol synthase-like side activity
physiological function
Q84V01
the enzyme is involved in the biosynthesis of proanthocyanidins and in seed coat color formation
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
B2M0X8, -
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + O2
show the reaction diagram
-, Q93VC3
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + O2
show the reaction diagram
A8RRU3, -
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2
show the reaction diagram
B2M0X8, -
-
-
-
?
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
show the reaction diagram
-
-
-
ir
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
show the reaction diagram
-
-
-
ir
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
show the reaction diagram
-
-
-
ir
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
show the reaction diagram
-
more detail to stereochemistry
-
ir
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
show the reaction diagram
-
using (2R,3S,4R)-leucocyanidin or (2R,3S,4R)-leucopelargonidin as substrates
-
ir
leucocyanidin + 2-oxoglutarate + O2 + H+
cyanidin + succinate + CO2 + 2 H2O
show the reaction diagram
A8RRU3, -
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + O2
show the reaction diagram
-
-
-
-
?
leucocyanidin + 2-oxoglutarate + O2 + H+
cyanidin + succinate + CO2 + 2 H2O
show the reaction diagram
B2M0X8, -
-
-
-
?
additional information
?
-
-
catalyzes the penultimate step in the biosynthesis of anthocyanin. This reaction is responsible for the formation of the colored anthocyanidins from the colorless leucoanthocyanidins
-
-
-
additional information
?
-
B2M0X8, -
catalyzes the penultimate step in the biosynthesis of the anthocyanin class of flavonoids, from the colorless leucoanthocyanidins to the colored anthocyanidins
-
-
-
additional information
?
-
B2M0X8, -
expression in abiotic stress responses. Up-regulated by all of the six tested abiotic stresses, UV-B, abscisic acid, sucrose, salicylic acid, cold and ethylene, consistent with the promoter region analysis of GbANS
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
?
-
-
catalyzes the penultimate step in the biosynthesis of anthocyanin. This reaction is responsible for the formation of the colored anthocyanidins from the colorless leucoanthocyanidins
-
-
-
additional information
?
-
B2M0X8, -
catalyzes the penultimate step in the biosynthesis of the anthocyanin class of flavonoids, from the colorless leucoanthocyanidins to the colored anthocyanidins
-
-
-
additional information
?
-
B2M0X8, -
expression in abiotic stress responses. Up-regulated by all of the six tested abiotic stresses, UV-B, abscisic acid, sucrose, salicylic acid, cold and ethylene, consistent with the promoter region analysis of GbANS
-
-
-
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Fe2+
-
contains
Fe2+
-
dependent on
Fe2+
-
dependent on
Iron
Q93VC3
Fe2+ is required
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.038
-
(2R,3S,4R)-leucocyanidin
-
-
0.059
-
2-oxoglutarate
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
-
-
pI VALUE
pI VALUE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5.18
-
Q84V01
sequence calculation
5.27
-
-
calculated from sequence
5.52
-
B2M0X8, -
-
5.9
-
A8RRU3, -
calculated
6.2
-
Q6QD85
calculated
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
-
primarily distributed in the exocarp, mesocarp, and seed of the fruit, developmentally dependent expression in skin and flesh
Manually annotated by BRENDA team
Vitis vinifera Cabernet Sauvignon
-
primarily distributed in the exocarp, mesocarp, and seed of the fruit, developmentally dependent expression in skin and flesh
-
Manually annotated by BRENDA team
Q84V01
all lines and seed coats of the black-seeded lines, not in the yellow-seeded seed coats
Manually annotated by BRENDA team
B2M0X8, -
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
B2M0X8, -
young and mature. Weakly expressed in mature leaves
Manually annotated by BRENDA team
-
lowest expression level
Manually annotated by BRENDA team
A9ZMJ5
low amount
Manually annotated by BRENDA team
-
primarily distributed in palisade and spongy tissues of the leaves
Manually annotated by BRENDA team
Vitis vinifera Cabernet Sauvignon
-
primarily distributed in palisade and spongy tissues of the leaves
-
Manually annotated by BRENDA team
Vitis vinifera Cabernet Sauvignon
-
-
-
Manually annotated by BRENDA team
B2M0X8, -
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
A8RRU3, -
levels of transcripts encoding anthocyanidin synthase, dihydroflavonol reductase and anthocyanidin reductase parallel the accumulation of proanthocyanidins in developing seeds
Manually annotated by BRENDA team
Q84V01
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
Q6QD85
abundant expression
Manually annotated by BRENDA team
B2M0X8, -
and graft
Manually annotated by BRENDA team
B2M0X8, -
moderate expression level
Manually annotated by BRENDA team
-
lowest expression level
Manually annotated by BRENDA team
-
primarily distributed in the primary phloem and pith ray in the stems
Manually annotated by BRENDA team
Vitis vinifera Cabernet Sauvignon
-
primarily distributed in the primary phloem and pith ray in the stems
-
Manually annotated by BRENDA team
-
perilla, red or green
Manually annotated by BRENDA team
-
primarily distributed in the growth point and leaf primordium of the leaf buds
Manually annotated by BRENDA team
additional information
Q6QD85
abundant expression in the red cell line, weak expression in the yellow cell line. No expression in root
Manually annotated by BRENDA team
additional information
B2M0X8, -
GbANS transcripts are not detected in the stems and roots
Manually annotated by BRENDA team
additional information
-
expression and tissue localization of ANS in different Cabernet Sauvignon samples, overview
Manually annotated by BRENDA team
additional information
Vitis vinifera Cabernet Sauvignon
-
expression and tissue localization of ANS in different Cabernet Sauvignon samples, overview
-
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
in the mesocarp vascular bundle and leaf bud cells
Manually annotated by BRENDA team
Vitis vinifera Cabernet Sauvignon
-
in the mesocarp vascular bundle and leaf bud cells
-
Manually annotated by BRENDA team
Vitis vinifera Cabernet Sauvignon
-
mainly
-
Manually annotated by BRENDA team
additional information
-
subcellular localization of ANS in different Cabernet Sauvignon samples, overview
-
Manually annotated by BRENDA team
additional information
Vitis vinifera Cabernet Sauvignon
-
subcellular localization of ANS in different Cabernet Sauvignon samples, overview
-
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
40000
-
B2M0X8, -
with a His-tag, Western Blot, SDS-PAGE
40450
-
-
calculated
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
Q93VC3
x * 41000, SDS-PAGE
?
Q6QD85
x * 40300, calculated
?
A8RRU3, -
x * 40000, calculated
?
-
x * 40450, calculated from sequence
?
Q84V01
x * 40862, sequence calculation
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
of recombinant enzyme
-
of recombinant enzyme
-
affinity chromatography
B2M0X8, -
of recombinant enzyme
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
overexpression in Escherichia coli
-
overexpression in Escherichia coli
-
gene BjANS, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree
Q84V01
expressed in Escherichia coli
B2M0X8, -
expressed in Escherichia coli strain DH5alpha
-
expression in Escherichia coli, overexpression in rice mutant Nootripathu, which accumulates proanthocyanidins exclusively in pericarp
Q93VC3
overexpression in Escherichia coli
-
overexpression in Escherichia coli
-
expression in Escherichia coli JM109
A9ZMJ5
analysis of expression in wheat-rye hybrids
C7S854, -
overexpression in Escherichia coli
-
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
decrease at stage of flowering
A9ZMJ5
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
wild-type and ldox/fls1-2 double mutant, lacking leucoanthocyanidin dioxygenase and functional flavonol synthase 1-2, EC 1.14.11.23
additional information
-
the IbANS expression profile in different sweet potato cultivars corresponded to the pattern of anthocyanin accumulation
additional information
-
expression of maize leaf colour regulatory gene Lc results in increased mRNA levels for phenylalanine ammonia-lyase, chalcone synthase, flavanone 3beta-hydroxylase, dihydroxavonol 4-reductase, leucoanthocyanidin reductases, anthocyanidin synthase and anthocyanidin reductase. In leaf tissue of transgenic lines, increased levels are detected of the anthocyanin idaein, the flavan 3-ol epicatechin, and especially the isomeric catechin, and some distinct dimeric proanthocyanidins
additional information
-, P51091
shift in polyphenol profile and sublethal phenotype caused by silencing the enzyme, comparison to 4 transgenic plants of different lines
additional information
A8RRU3, -
down-regulation by antisense-RNA results in reduced anthocyanin and proanthocyanin levels, but has no impact on flavonol levels
additional information
Q93VC3
expression in maize a2 mutant results in production of anthocyanins in the aleurione. Transgenic rice mutant Nootripathu plants which accumulate proanthocyanidins exclusively in pericarp, channel the proanthocyanidin precursors to the production of anthocyanidin upon overexpression of enzyme. Transgenic rice plants show an increased accumulation of a mixture of flavonoids and anthocyanins with concomitant decrease in proanthocyanidins
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
agriculture
-
basis work for molecular directional breeding of sweet potato
additional information
C7S854, -
the specific primer pairs developed for rye ABP genes represent effective rye chromosome-specific markers and can be used for chromosome identification in wheat-rye hybrids