BRENDA - Enzyme Database
show all sequences of 1.17.1.3

Crystal structure and catalytic mechanism of leucoanthocyanidin reductase from Vitis vinifera

Mauge, C.; Granier, T.; dEstaintot, B.L.; Gargouri, M.; Manigand, C.; Schmitter, J.M.; Chaudiere, J.; Gallois, B.; J. Mol. Biol. 397, 1079-1091 (2010)

Data extracted from this reference:

Cloned(Commentary)
Cloned (Commentary)
Organism
expression of His-tagged LAR1 in Escherichia coli
Vitis vinifera
Crystallization (Commentary)
Crystallization (Commentary)
Organism
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
Vitis vinifera
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
additional information
Vitis vinifera
leucoanthocyanidin reductase catalyzes the NADPH-dependent reduction of 2R,3S,4S-flavan-3,4-diols into 2R,3S-flavan-3-ols
?
-
-
-
Organism
Organism
UniProt
Commentary
Textmining
Vitis vinifera
Q4W2K4
LAR1
-
Purification (Commentary)
Purification (Commentary)
Organism
recombinant His-tagged LAR1 from Escherichia coli by nickel affinity chromatography
Vitis vinifera
Reaction
Reaction
Commentary
Organism
Reaction ID
(2R,3S)-catechin + NADP+ + H2O = 2,3-trans-3,4-cis-leucocyanidin + NADPH + H+
two-step catalytic mechanism involving the formation of an enzyme-bound quinone methide intermediate prior to reduction, overview. A concerted dehydration precedes an NADPH-mediated hydride transfer at C4. The dehydration step involves a Lys-catalyzed deprotonation of the phenolic OH7 through a bridging water molecule and a His-catalyzed protonation of the benzylic hydroxyl at C4. The resulting quinone methide serves as an electrophilic target for hydride transfer at C4. The role of the lysine is to promote the formation of this intermediate by catalyzing the deprotonation of a phenolic hydroxyl
Vitis vinifera
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
additional information
leucoanthocyanidin reductase catalyzes the NADPH-dependent reduction of 2R,3S,4S-flavan-3,4-diols into 2R,3S-flavan-3-ols
715907
Vitis vinifera
?
-
-
-
-
additional information
the coenzyme and substrate binding pocket is preformed in the apoprotein and not markedly altered upon NADPH binding, ternary complex structure, substrate binding site structure, overview. Ordering of a short 3_10 helix associated with substrate binding, His122 and Lys140 act as acid-base catalysts
715907
Vitis vinifera
?
-
-
-
-
Subunits
Subunits
Commentary
Organism
?
x * 46943.3, recombinant enzyme, mass spectrometry
Vitis vinifera
More
three-dimensional structure and structure comparisons, overview
Vitis vinifera
Synonyms
Synonyms
Commentary
Organism
LAR
-
Vitis vinifera
LAR1
-
Vitis vinifera
leucoanthocyanidin reductase
-
Vitis vinifera
More
LAR belongs to the short-chain dehydrogenase/reductase superfamily and to the PIP (pinoresinol-lariciresinol reductase, isoflavone reductase, and phenylcoumaran benzylic ether reductase) family
Vitis vinifera
Cofactor
Cofactor
Commentary
Organism
Structure
NADPH
dependent on, binding site structure, overview
Vitis vinifera
Cloned(Commentary) (protein specific)
Commentary
Organism
expression of His-tagged LAR1 in Escherichia coli
Vitis vinifera
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADPH
dependent on, binding site structure, overview
Vitis vinifera
Crystallization (Commentary) (protein specific)
Crystallization
Organism
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
Vitis vinifera
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
additional information
Vitis vinifera
leucoanthocyanidin reductase catalyzes the NADPH-dependent reduction of 2R,3S,4S-flavan-3,4-diols into 2R,3S-flavan-3-ols
?
-
-
-
Purification (Commentary) (protein specific)
Commentary
Organism
recombinant His-tagged LAR1 from Escherichia coli by nickel affinity chromatography
Vitis vinifera
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
additional information
leucoanthocyanidin reductase catalyzes the NADPH-dependent reduction of 2R,3S,4S-flavan-3,4-diols into 2R,3S-flavan-3-ols
715907
Vitis vinifera
?
-
-
-
-
additional information
the coenzyme and substrate binding pocket is preformed in the apoprotein and not markedly altered upon NADPH binding, ternary complex structure, substrate binding site structure, overview. Ordering of a short 3_10 helix associated with substrate binding, His122 and Lys140 act as acid-base catalysts
715907
Vitis vinifera
?
-
-
-
-
Subunits (protein specific)
Subunits
Commentary
Organism
?
x * 46943.3, recombinant enzyme, mass spectrometry
Vitis vinifera
More
three-dimensional structure and structure comparisons, overview
Vitis vinifera
General Information
General Information
Commentary
Organism
physiological function
leucoanthocyanidin reductase catalyzes the NADPH-dependent reduction of 2R,3S,4S-flavan-3,4-diols into 2R,3S-flavan-3-ols, a subfamily of flavonoids that is important for plant survival and for human nutrition
Vitis vinifera
General Information (protein specific)
General Information
Commentary
Organism
physiological function
leucoanthocyanidin reductase catalyzes the NADPH-dependent reduction of 2R,3S,4S-flavan-3,4-diols into 2R,3S-flavan-3-ols, a subfamily of flavonoids that is important for plant survival and for human nutrition
Vitis vinifera
Other publictions for EC 1.17.1.3
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Synonyms
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
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Metabolic characterization of ...
Camellia sinensis
Molecules
22
E2241
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205
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1
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3
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3
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8
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24
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3
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1
3
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745869
Liu
A role for leucoanthocyanidin ...
Medicago truncatula, Medicago truncatula ecotype R108
Nat. Plants
2
16182
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1
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2
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4
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4
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1
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6
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3
3
1
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Different alleles of a gene e ...
Picea abies
Plant Physiol.
171
2671-2681
2016
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1
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5
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2
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744993
Liao
Molecular characterization of ...
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Front. Plant Sci.
6
243
2015
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4
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15
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745035
Wen
Accumulation of flavanols and ...
Vitis vinifera
Genet. Mol. Res.
14
7687-7695
2015
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728635
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Transcriptome and biochemical ...
Gossypium hirsutum
PLoS ONE
9
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2014
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1
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746499
Kim
Transcripts of anthocyanidin ...
Fagopyrum tataricum
ScientificWorldJournal
2014
726567
2014
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1
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1
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9
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9
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1
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1
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3
3
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726337
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Isolation and characterization ...
Populus trichocarpa
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8
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2013
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727256
Liu
Proanthocyanidin synthesis in ...
Theobroma cacao
BMC Plant Biol.
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202
2013
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746103
Pang
Mewan, K.M.; Sumner, L.W.; Yu ...
Camellia sinensis
Plant Physiol.
161
1103-1116
2013
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728054
Yuan
Molecular cloning and characte ...
Populus trichocarpa
J. Exp. Bot.
63
2513-2524
2012
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714393
Wang
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Isolation and expression of ge ...
Diospyros kaki, Diospyros kaki Luotian-tianshi
Biol. Plant.
54
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2010
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715907
Mauge
Crystal structure and catalyti ...
Vitis vinifera
J. Mol. Biol.
397
1079-1091
2010
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1
1
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716027
Lacampagne
-
Involvement of abscisic acid i ...
Vitis vinifera
J. Plant Growth Regul.
29
81-90
2010
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1
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2
2
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700789
Gagne
Leucoanthocyanidin reductase a ...
Vitis vinifera
Plant Physiol. Biochem.
47
282-290
2009
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2
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6
1
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6
1
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1
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676629
Paolocci
Ectopic expression of a basic ...
Lotus corniculatus
Plant Physiol.
143
504-516
2007
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1
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5
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1
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676650
Pfeiffer
Biosynthesis of flavan 3-ols b ...
Malus domestica, Vitis vinifera
Plant Physiol. Biochem.
44
323-334
2006
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7
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2
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15
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3
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2
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4
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15
-
4
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4
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676588
Bogs
Proanthocyanidin synthesis and ...
Vitis vinifera
Plant Physiol.
139
652-663
2005
-
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