Information on EC 1.3.1.112 - anthocyanidin reductase [(2S)-flavan-3-ol-forming]

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The expected taxonomic range for this enzyme is: Vitis vinifera

EC NUMBER
COMMENTARY hide
1.3.1.112
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RECOMMENDED NAME
GeneOntology No.
anthocyanidin reductase [(2S)-flavan-3-ol-forming]
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a (2S,3R)-flavan-3-ol + 2 NADP+ = an anthocyanidin with a 3-hydroxy group + 2 NADPH + H+
show the reaction diagram
(1)
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a (2S,3S)-flavan-3-ol + 2 NADP+ = an anthocyanidin with a 3-hydroxy group + 2 NADPH + H+
show the reaction diagram
(2)
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SYSTEMATIC NAME
IUBMB Comments
(2S)-flavan-3-ol:NAD(P)+ oxidoreductase
The enzyme, characterized from Vitis vinifera (grape), participates in the flavonoid biosynthesis pathway. It catalyses the double reduction of anthocyanidins, producing a mixture of (2S,3S)- and (2S,3R)-flavan-3-ols. The enzyme catalyses sequential hydride transfers to C-2 and C-4, respectively. Epimerization at C-3 is achieved by tautomerization that occurs between the two hydride transfers. cf. EC 1.3.1.77, anthocyanidin reductase [(2R,3R)-flavan-3-ol-forming].
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
cyanidin + 2 NADPH + 2 H+
(+)-epicatechin + (-)-catechin + 2 NADP+
show the reaction diagram
cyanidin + 2 NADPH + 2 H+
epicatechin + 2 NADP+
show the reaction diagram
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-
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?
delphinidin + 2 NADPH + 2 H+
(-)-gallocatechin + (+)-epigallocatechin + 2 NADP+
show the reaction diagram
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-
-
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irr
delphinidin + 2 NADPH + 2 H+
epigallocatechin + 2 NADP+
show the reaction diagram
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-
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?
paeonidin + 2 NADPH + 2 H+
? + 2 NADP+
show the reaction diagram
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-
-
?
pelargonidin + 2 NADPH + 2 H+
(-)-afzelechin + (+)-epiafzelechin + 2 NADP+
show the reaction diagram
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-
-
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irr
pelargonidin + 2 NADPH + 2 H+
epiafzelechin + 2 NADP+
show the reaction diagram
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-
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?
petunidin + 2 NADPH + 2 H+
? + 2 NADP+
show the reaction diagram
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-
?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
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hyperbolic binding of NADPH and NADP+ to the free enzyme, with a single binding site each and with dissociation constants of 0.046 mM for NADPH and 0.083 for NADP+
NADPH
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hyperbolic binding of NADPH and NADP+ to the free enzyme, with a single binding site each and with dissociation constants of 0.046 mM for NADPH and 0.083 for NADP+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
sodium chloride
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complete inhibition above 200 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0028
cyanidin
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pH 7.5, 30°C
0.111
NADPH
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pH 7.5, 30°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
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assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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grape flowers have high levels of proanthocyanidins. ANR is expressed throughout early flower and berry development
Manually annotated by BRENDA team
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grape skin
Manually annotated by BRENDA team
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grape flowers have high levels of proanthocyanidins, and accumulation continues in skin and seeds from fruit set until the onset of ripening. ANR is expressed throughout early flower and berry development, with expression increasing after fertilization. During grape ripening, proanthocyanidin levels decrease in both skin and seeds, and expression of genes encoding ANR and LAR are no longer detected
Manually annotated by BRENDA team
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 43000, SDS-PAGE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
to 2.2 A resolution. The active site is wide open with the side chains of the catalytic residues Tyr168 and Lys172 turned away from the nucleotide-binding site
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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expression in Saccharomyces cerevisiae
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
trreatment with abscisic acid affects tannin content and is involved in the tannin biosynthesis pathway in grape skin by decreasing leucoanthocyanidin reductase and ANR activity and repressing the expression of related genes a few days after application
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