Information on EC 1.17.1.3 - leucoanthocyanidin reductase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.17.1.3
-
RECOMMENDED NAME
GeneOntology No.
leucoanthocyanidin reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2R,3S)-catechin + NADP+ + H2O = 2,3-trans-3,4-cis-leucocyanidin + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
2,3-trans-flavanols biosynthesis
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-
proanthocyanidins biosynthesis from flavanols
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Flavonoid biosynthesis
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
(2R,3S)-catechin:NADP+ 4-oxidoreductase
The enzyme catalyses the synthesis of catechin, catechin-4beta-ol (leucocyanidin) and the related flavan-3-ols afzelechin and gallocatechin, which are initiating monomers in the synthesis of plant polymeric proanthocyanidins or condensed tannins. While 2,3-trans-3,4-cis-leucocyanidin is the preferred flavan-3,4-diol substrate, 2,3-trans-3,4-cis-leucodelphinidin and 2,3-trans-3,4-cis-leucopelargonidin can also act as substrates, but more slowly. NADH can replace NADPH but is oxidized more slowly.
CAS REGISTRY NUMBER
COMMENTARY hide
190337-34-9
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93389-48-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
cvs. Sachiizumi, Harunoibuki, 2SL05-1, Asahimurazairai, and Asahimurazairai/Kyushu PL4, from Japan
UniProt
Manually annotated by BRENDA team
cvs. Hokkai T8 and Hokkai T10
V9PJ26
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
barley
-
-
Manually annotated by BRENDA team
var. nana, Aihuahong
-
-
Manually annotated by BRENDA team
var. nana, Aihuahong
-
-
Manually annotated by BRENDA team
Xiongyuehaitang
-
-
Manually annotated by BRENDA team
Xijinhaitang
-
-
Manually annotated by BRENDA team
Medicago truncatula ecotype R108
-
UniProt
Manually annotated by BRENDA team
4 different populations
UniProt
Manually annotated by BRENDA team
douglas fir
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
metabolism
physiological function
additional information
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)-dihydromyricetin + NADPH
gallocatechin + NADP+ + H2O
show the reaction diagram
-
combined dihydroflavonol 4-reductase/leucoanthocyanidin 4-reductae activity
-
-
?
(2R,3R)-dihydroquercetin + NADPH
(2R,3S)-catechin + NADP+ + H2O
show the reaction diagram
-
combined dihydroflavonol 4-reductase/leucoanthocyanidin 4-reductae activity, 2-step reaction
-
-
?
(2R,3S)-catechin + NADP+ + H2O
2,3-trans-3,4-cis-leucocyanidin + NADPH + H+
show the reaction diagram
(2S)-eriodictyol + NADPH
luteoliflavan + NADP+ + H2O
show the reaction diagram
-
flavan formation by combined flavanone 4-reductase/leucoanthocyanidin 4-reductae activity
-
-
?
(2S)-naringenin + NADPH
?
show the reaction diagram
-
flavan formation by combined flavanone 4-reductase/leucoanthocyanidin 4-reductae activity
-
-
?
2,3-trans-3,4-cis-leucoanthocyanidin + NADPH
(2R,3S)-catechin + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
2,3-trans-3,4-cis-leucocyanidin + NADPH
(2R,3S)-catechin + NADP+ + H2O
show the reaction diagram
2,3-trans-3,4-cis-leucocyanidin + NADPH + H+
(2R,3S)-catechin + NADP+ + H2O
show the reaction diagram
3,4-cis-leucoanthocyanidin + NADPH
2,3-trans-catechin + NADP+ + H2O
show the reaction diagram
3,4-cis-leucodelphinidin + NADPH
2,3-trans-gallocatechin + NADP+ + H2O
show the reaction diagram
-
-
-
?
3,4-cis-leucodelphinidin + NADPH
? + NADP+ + H2O
show the reaction diagram
3,4-cis-leucopelargonidin + NADPH
2,3-trans-afzelechin + NADP+ + H2O
show the reaction diagram
-
-
-
?
3,4-cis-leucopelargonidin + NADPH
? + NADP+ + H2O
show the reaction diagram
4beta-(S-cysteinyl)-epicatechin + NADPH + H+
epicatechin + cysteine + NADP+
show the reaction diagram
cyanidin + NADPH
(-)-epicatechin + (-)-catechin + NADP+ + H2O
show the reaction diagram
cyanidin + NADPH
(-)-epicatechin + NADP+ + H2O
show the reaction diagram
delphinidin + NADPH
(-)-epigallocatechin + (-)-gallocatechin + NADP+ + H2O
show the reaction diagram
dihydroquercetin + NADPH
(2R,3S)-catechin + NADP+ + H2O
show the reaction diagram
dihydroquercetin + NADPH + H+
(+)-catechin + NADP+ + H2O
show the reaction diagram
-
-
-
?
dihydroquercetin + NADPH + H+
(2R,3S)-catechin + NADP+ + H2O
show the reaction diagram
-
-
-
?
leucodelphinidin + NADPH
? + NADP+ + H2O
show the reaction diagram
luteoforol + NADPH
luteoliflavan + NADP+ + H2O
show the reaction diagram
pelargonidin + NADPH
(-)-epiafzelechin + (-)-afzelechin + NADP+ + H2O
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)-catechin + NADP+ + H2O
2,3-trans-3,4-cis-leucocyanidin + NADPH + H+
show the reaction diagram
2,3-trans-3,4-cis-leucocyanidin + NADPH
(2R,3S)-catechin + NADP+ + H2O
show the reaction diagram
2,3-trans-3,4-cis-leucocyanidin + NADPH + H+
(2R,3S)-catechin + NADP+ + H2O
show the reaction diagram
3,4-cis-leucoanthocyanidin + NADPH
2,3-trans-catechin + NADP+ + H2O
show the reaction diagram
Q84V83
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no formation of 2,3-cis-epicatechin
-
?
4beta-(S-cysteinyl)-epicatechin + NADPH + H+
epicatechin + cysteine + NADP+
show the reaction diagram
cyanidin + NADPH
(-)-epicatechin + NADP+ + H2O
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
enzyme is not affected by Na+ at up to 400 mM
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-catechin
-
-
2,3-cis-flavan-3,4-diol
slight inhibition
2,3-cis-flavan-3-ol
product inhibition
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromenium
48% inhibition at 0.006 mM
3,4-trans-leucocyanidin
50% inhibition at 0.12 mM
3,4-trans-leucopelargonidin
50% inhibition at 0.46 mM
afzelechin
50% inhibition at 0.014 mM
catechin
50% inhibition at 0.012 mM
cyanidin
-
substrate inhibition at high concentration
delphinidin
97% inhibition at 0.06 mM
dihydroquercetin
epi-gallocatechin
50% inhibition at 1.4 mM
eriodictyol
53% inhibition at 0.01 mM
gallocatechin
50% inhibition at 0.28 mM
Na+
-
above 200 mM
NADP+
50% inhibition at 0.5 mM; slight inhibition
pelargonidin
quercetin
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.006
2,3-trans-3,4-cis-leucocyanidin
pH 7.0, 30°C
0.006
3,4-cis-leucoanthocyanidin
pH 7.0, 30°C
0.005
3,4-cis-leucodelphinidin
pH 7.0, 30°C; pH 7.0, 30°C
0.026
3,4-cis-leucopelargonidin
pH 7.0, 30°C; pH 7.0, 30°C
0.037
dihydroquercetin
-
pH 7.4
0.06
NADH
pH 7.0, 30°C
0.0004 - 0.042
NADPH
additional information
additional information
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0005
-
crude extract of young leafs
8.7
; purified native enzyme, substrate 2,3-trans-3,4-cis-leucoanthocyanidin
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 6
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depending on the buffer system used
6
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assay at, combined flavanone 4-reductase/leucoanthocyanidin 4-reductae activity
7.6
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combined dihydroflavonol 4-reductase/leucoanthocyanidin 4-reductae activity
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 7.5
-
80% activity at pH 6 and pH 7.5
6 - 7
both isoforms LAR1 and LAR2; both isoforms LAR1 and LAR2
6 - 7.5
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80% activity at pH 6 and pH 7.5
6 - 7
Q3S9L6;, Q4W2K5;
both isoforms LAR1 and LAR2; both isoforms LAR1 and LAR2
6.2 - 7.8
95% activity at pH 6.2 and pH 7.8; 95% of maximal activity at pH 76.2 and pH 7.8
6.4 - 8
-
no significant changes between pH 6.4 and pH 8.0
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22
assay at room temperature
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.34
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
low expression
Manually annotated by BRENDA team
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pod exocarp
Manually annotated by BRENDA team
berry skin, lower level of LAR2 expression than in seed; berry skin, low level of LAR1 expression
Manually annotated by BRENDA team
V9PJ26;
grown under light or dark condition
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
UNIPROT
ORGANISM
Vitis vinifera;
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45000
1 * 45000, native enzyme, SDS-PAGE; 1 * 45000, SDS-PAGE
52000
gel filtration; native enzyme, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
1 * 45000, native enzyme, SDS-PAGE; 1 * 45000, SDS-PAGE
additional information
three-dimensional structure and structure comparisons, overview
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
near homogeneity
LAR1 in complex with or without NADPH and one of its natural products, (+)-catechin, X-ray diffraction structure determination and analysis at 1.75-2.72 A resolution
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
only little loss of activity after freezing and thawing
-
unstable in desalted extracts
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, desalted extract, 40% loss of activity after 90 min
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4°C, desalted extract, only little loss of activity after 90 min
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme to near homogeneity from leaves, about 48500fold
recombinant enzyme from Escherichia coli
recombinant His-tagged LAR1 from Escherichia coli by nickel affinity chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
; determination of DNA and amino acid sequences, expression in Escherichia coli strain XL-1 Blue, Nicotiana tabacum, and Trifolium repens, plant transformations via Agrobacterium tumefaciens infection system
ectopic expression of CsLAR leads to the formation of (+)-catechin, but also of (-)-epicatechin in anthocyanin producing tissues of tobacco plants
expression in Escherichia coli strain BL21(DE3)
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expression in Escherichia coli strain DH5alpha, expression as MBT-fusion protein followed by cleavage of the protein tag by Factor Xa protease
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expression of His-tagged LAR1 in Escherichia coli
gene DkLAR, DNA and amino acid sequence determination and analysis, genotyping and phylogenetic analysis. Expression of the DkLAR gene in Chinese pollination-constant non-astringent, PCNA, genotype is coincident with the tannin cell development, but is not in Japanese PCNA and Chinese pollination-variant astringent PCA genotypes; gene DkLAR, DNA and amino acid sequence determination and analysis, genotyping. Expression of the DkLAR gene in Chinese pollination-constant non-astringent, PCNA, genotype is coincident with the tannin cell development, but is not in Japanese PCNA and Chinese pollination-variant astringent PCA genotypes
E4W4T1;
gene LAR, co-overexpression with anthocyanidin reductase (ANR) in Nicotiana tabacum cv. Xanthi by Agrobacterium tumefaciens-mediated transformation, semiquantitative expression analysis
gene lar, DNA and amino acid sequence determination and analysis, sequence comaprisons and phylogenetic analysis, cloned from two cultivars, Hokkai T8 and T10, quantitative real-time RT-PCR enzyme expression analysis
V9PJ26;
gene lar, overexpression of the enzyme in Medicago truncatula hairy roots, conversion of 4beta-(S-cysteinyl)-epicatechin to epicatechin by recombinant LAR
gene LAR, quantitative real-time PCR enzyme expression analysis
gene LAR1, cloned from leaves, DNA and amino acid sequence determination and analysis, genotyping, the three LAR loci, FeLAR1, FeLAR2, and FeLAR3, are not genetically linked, phylogenetic analysis; gene LAR2, cloned from leaves, DNA and amino acid sequence determination and analysis, genotyping, the three LAR loci, FeLAR1, FeLAR2, and FeLAR3, are not genetically linked, phylogenetic analysis; gene LAR3, cloned from leaves, DNA and amino acid sequence determination and analysis, genotyping, the three LAR loci, FeLAR1, FeLAR2, and FeLAR3, are not genetically linked, phylogenetic analysis
gene LAR1, quantitative real-time PCR enzyme expression analysis, recombinant expression in Nicotiana tabacum cv. Petite Havana SR1 using the transfection method with Agrobacterium tumefaciens strain GV3101 and under control of the CaMV 35S promoter. The proanthocyanidin contents in either white- or pale pink-colored transgenic flowers are significantly lower than that of wild-type flowers. In contrast, both pale-pink and white flowers of the transgenic lines accumulate slightly higher levels of epicatechin than wild-type flowers, but the changes do not reach statistical significance. No significant change in catechin content is observed between wild-type flowers and either white- or pale pink-colored transgenic flowers, phenotypes, overview; gene LAR, quantitative real-time PCR enzyme expression analysis
gene LAR3, DNA and amino acid sequence determination, genotyping, genetic organization and allelic structure of the gene, identification of nonsynonymous substitutions, and to analysis of motifs in the promoter, recombinant expression in Nicotiana benthamiana, and quantitative RT-PCR analyis of allele-specific gene expression of the PaLAR3 alleles
gene LARa, complementary DNA library construction, DNA and amino acid sequence determination and analysis, phylogenetic analysis and tree, functional expression of His6-tagged enzyme in Escherichia coli strain M15. Recombinant ectopic expression of CsLAR leads to the accumulation of low levels of proanthocyanidin precursors and their conjugates in Medicago truncatula hairy roots and anthocyanin-overproducing Nicotiana tabacum, but levels of oligomeric proanthocyanidins are very low. The expression of CsLAR in tobacco overproducing anthocyanin leads to the accumulation of higher levels of epicatechin and its glucoside than of catechin, phenotype and flavonoid compounds contents, overview
gene LARa, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, recombinant expression in Escherichia coli, recombinant expression in transgenic Nicotianan tabacum and Arabidopsis thaliana via Agrobacterium tumefaciens strains EHA105 and C58C1?mediated transformation, quantitative real?time PCR enzyme expression analysis. In Arabidopsis thaliana, contents of both insoluble and soluble proanthocyanidins extracted from the seeds are reduced in the overexpressing CsLARs lines compared with wild-type, although CsLARs catalyze leucocyanidins conversion to catechin in vitro, no catechin is detected in any transgenic Arabidopsis thaliana lines. Also no proanthocyanidins are detected in the transgenic tobacco; gene LARb, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, recombinant expression in Escherichia coli, recombinant expression in transgenic Nicotianan tabacum and Arabidopsis thaliana via Agrobacterium tumefaciens strains EHA105 and C58C1-mediated transformation, quantitative real-time PCR enzyme expression analysis. In Arabidopsis thaliana, contents of both insoluble and soluble proanthocyanidins extracted from the seeds are reduced in the overexpressing CsLARs lines compared with wild-type, although CsLARs catalyze leucocyanidins conversion to catechin in vitro, no catechin is detected in any transgenic Arabidopsis thaliana lines. Also no proanthocyanidins are detected in the transgenic tobacco; gene LARc, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, recombinant expression in Escherichia coli, recombinant expression in transgenic Nicotianan tabacum and Arabidopsis thaliana via Agrobacterium tumefaciens strain s EHA105 and C58C1-mediated transformation, quantitative real-time PCR enzyme expression analysis. In Arabidopsis thaliana, contents of both insoluble and soluble proanthocyanidins extracted from the seeds are reduced in the overexpressing CsLARs lines compared with wild-type, although CsLARs catalyze leucocyanidins conversion to catechin in vitro, no catechin is detected in any transgenic Arabidopsis thaliana lines. Also no proanthocyanidins are detected in the transgenic tobacco; gene LARc, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, recombinant expression in Escherichia coli, recombinant expression in transgenic Nicotianan tabacum and Arabidopsis thaliana via Agrobacterium tumefaciens strain s EHA105 and C58C1?mediated transformation, quantitative real?time PCR enzyme expression analysis. In Arabidopsis thaliana, contents of both insoluble and soluble proanthocyanidins extracted from the seeds are reduced in the overexpressing CsLARs lines compared with wild-type, although CsLARs catalyze leucocyanidins conversion to catechin in vitro, no catechin is detected in any transgenic Arabidopsis thaliana lines. Also no proanthocyanidins are detected in the transgenic tobacco
genes Vv lar1 and Vv lar2, quantitative real-time RT-PCR enzyme expression analysis; genes Vvlar1 and Vvlar2, quantitative real-time RT-PCR enzyme expression analysis
recombinantly expressed in Escherichia coli
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
highest expression in roots
-
leucoanthocyanidin reductase expression in cotton fiber is much higher than their competing enzymes acting on the same substrates (dihydroflavonol 4-reductase and anthocyanidin synthase, respectively); significantly up-regulated in brown fiber
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overexpression of the myeloblastosis (MYB)14 or MYB5 transcription factors induces proanthocyanidin biosynthesis in hairy roots, LAR is induced in MYB5 overexpressing hairy roots
UV-C irradiation induced the transcription of Vv lar1 and Vv lar2 and the synthesis of LAR1 and LAR2 proteins, resulting in increased accumulation of flavanol polyphenol in the grape berries, quantitative real-time RT-PCR enzyme expression analysis, overview; UV-C irradiation induces the transcription of Vv lar1 and Vv lar2 and the synthesis of LAR1 and LAR2 proteins, resulting in increased accumulation of flavanol polyphenol in the grape berries, quantitative real-time RT-PCR enzyme expression analysis, overview
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information