Information on EC 1.17.1.3 - leucoanthocyanidin reductase

New: Word Map on EC 1.17.1.3
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Mark a special word or phrase in this record:
Search Reference ID:
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


The expected taxonomic range for this enzyme is: Spermatophyta

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
-
-
Biosynthesis of secondary metabolites
-
-
Flavonoid biosynthesis
-
-
proanthocyanidins biosynthesis from flavanols
-
-
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
-
93389-48-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
Diospyros kaki Luotian-tianshi
-
-
-
Manually annotated by BRENDA team
barley
-
-
Manually annotated by BRENDA team
douglas fir
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
-
leucoanthocyanidin reductase and anthocyanidin reductase are involved in biosynthesis of proanthocyanidins or condensed tannins by producing (+)-catechin and (-)-epicatechin, respectively, from leukoanthocyanidin
physiological function
additional information
-
leucoanthocyanidin reductase and anthocyanidin reductase are co-regulated by abscisic acid, overview
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
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
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
3,4-cis-leucoanthocyanidin + NADPH
2,3-trans-catechin + NADP+ + H2O
show the reaction diagram
Q84V83
-
no formation of 2,3-cis-epicatechin
-
?
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
0.005
3,4-cis-leucodelphinidin
pH 7.0, 30C; pH 7.0, 30C
0.026
3,4-cis-leucopelargonidin
pH 7.0, 30C; pH 7.0, 30C
0.037
dihydroquercetin
-
pH 7.4
0.06
NADH
pH 7.0, 30C
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
-
depending on the buffer system used
6
-
assay at, combined flavanone 4-reductase/leucoanthocyanidin 4-reductae activity
7.5
-
assay at
7.6
-
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
-
80% activity at pH 6 and pH 7.5
6 - 7
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
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
low expression
Manually annotated by BRENDA team
-
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
-
low expression
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
52000
gel filtration; native enzyme, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 46943.3, recombinant enzyme, mass spectrometry
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
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4C, desalted extract, 40% loss of activity after 90 min
-
4C, desalted extract, only little loss of activity after 90 min
-
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
expression in Escherichia coli strain BL21(DE3)
-
expression in Escherichia coli strain DH5alpha, expression as MBT-fusion protein followed by cleavage of the protein tag by Factor Xa protease
-
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
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
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information