1.3.1.77: anthocyanidin reductase [(2R,3R)-flavan-3-ol-forming]
This is an abbreviated version!
For detailed information about anthocyanidin reductase [(2R,3R)-flavan-3-ol-forming], go to the full flat file.
Word Map on EC 1.3.1.77
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1.3.1.77
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anthocyanidins
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proanthocyanidins
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epicatechins
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camellia
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leucoanthocyanidin
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testa
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+-catechin
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flavan-3-ols
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cslar
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pelargonidin
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molecular biology
- 1.3.1.77
- anthocyanidins
- proanthocyanidins
- epicatechins
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camellia
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leucoanthocyanidin
- testa
-
+-catechin
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flavan-3-ols
- cslar
- pelargonidin
- molecular biology
Reaction
Synonyms
ANR, ANR1, ANR1-2, ANR1-3, ANR2, ANR2a, ANRa, ANRb, anthocyanidin reductase, anthocyanidin reductase 1, anthocyanidin reductase 2, AtANR, BAN, BANYULS, BEN1, BpANR, CsANR, CsANR1, CsANR2, CssANRa, CssANRb, dihydroflavonol 4-reductase-like protein, FeANR, GhANR1, MdLAR1, MtANR, PtrANR1, RrANR, VbANR
ECTree
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Substrates Products
Substrates Products on EC 1.3.1.77 - anthocyanidin reductase [(2R,3R)-flavan-3-ol-forming]
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REACTION DIAGRAM
(2R)-2-(3,4-dihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol + NADPH + H+
(2R,3R,4R)-2,3-cis-3,4-cis-leucocyanidin + NADP+
2 cyanidin + 4 NADPH + H+
(-)-catechin + (-)-epicatechin + 4 NADP+
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?
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?
2 delphinidin + 4 NADPH + H+
(-)-gallocatechin + (-)-epigallocatechin + 4 NADP+
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?
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?
2 pelargonidin + 4 NADPH + H+
(-)-afzelechin + (-)-epiafzelechin + 4 NADP+
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?
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?
2,3-cis-flavan-3-ol + NAD(P)+
anthocyanidin + NAD(P)H + H+
the enzyme is involved in formation of condensed tannins. The enzyme competes with anthocyanidin synthase, for the pool of flavan-3,4-diol
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?
2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-3,5,7-triol + NADPH + H+
(2R,3R)-epicatechin + NADP+
a (2R,3R)-flavan-3-ol + 2 NAD(P)+
an anthocyanidin with a 3-hydroxy group + 2 NAD(P)H + H+
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?
a (2R,3R)-flavan-3-ol + 2 NAD+
an anthocyanidin with a 3-hydroxy group + 2 NADH + H+
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?
a (2R,3R)-flavan-3-ol + 2 NADP+
an anthocyanidin with a 3-hydroxy group + 2 NADPH + H+
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?
an anthocyanidin with a 3-hydroxy group + 2 NADH + H+
a (2R,3R)-flavan-3-ol + 2 NAD+
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-
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?
anthocyanidin + 2 NADPH + H+
(-)-epicatechin + 2 NADP+
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?
anthocyanidin + 2 NADPH + H+
2,3-trans-(2S,3R)-flavan-3-ol + 2 NADP+
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?
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?
cyanidin + 2 NADPH + 2 H+
(-)-catechin + (-)-epicatechin + 2 NADP+
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?
cyanidin + 2 NADPH + H+
epicatechin + catechin + 2 NADP+
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?
delphinidin + 2 NADH + 2 H+
(-)-epigallocatechin + (-)-gallocatechin + 2 NAD+
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?
delphinidin + NADPH
(-)-epigallocatechin + NAD(P)+
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changes in the concentration of products and coenzyme in the ANR assay are determined by thin layer chromatography (TLC), HPLC, mass spectrometry (MS) and UV spectrophotometry
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-
?
pelargonidin + 2 NADPH + 2 H+
(-)-epiafzelechin + (-)-afzelechin + 2 NADP+
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?
(2R,3R,4R)-2,3-cis-3,4-cis-leucocyanidin + NADP+
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?
(2R)-2-(3,4-dihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol + NADPH + H+
(2R,3R,4R)-2,3-cis-3,4-cis-leucocyanidin + NADP+
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-
-
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?
(2R)-2-(3,4-dihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol + NADPH + H+
(2R,3R,4R)-2,3-cis-3,4-cis-leucocyanidin + NADP+
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?
(2R,3R)-epicatechin + NADP+
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?
2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-3,5,7-triol + NADPH + H+
(2R,3R)-epicatechin + NADP+
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-
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?
2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-3,5,7-triol + NADPH + H+
(2R,3R)-epicatechin + NADP+
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-
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?
a (2R,3R)-flavan-3-ol + 2 NADP+
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?
an anthocyanidin with a 3-hydroxy group + 2 NADPH + H+
a (2R,3R)-flavan-3-ol + 2 NADP+
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-
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?
an anthocyanidin with a 3-hydroxy group + 2 NADPH + H+
a (2R,3R)-flavan-3-ol + 2 NADP+
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-
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?
2,3-cis-flavan-3-ol + NAD(P)+
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enzyme of flavonoid pathway involved in the biosynthesis of condensed tannins
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?
anthocyanidin + NAD(P)H
2,3-cis-flavan-3-ol + NAD(P)+
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enzyme of flavonoid pathway involved in the biosynthesis of condensed tannins
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?
cyanidin + 2 NADPH + H+
(2R,3R)-epicatechin + 2 NADP+
Medicago truncatula ecotype R108
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?
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?
cyanidin + NADPH
(-)-epicatechin + NAD(P)+
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preference of anthocyanidin substrates in decreasing order: cyanidin, pelargonidin and delphinidin
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?
(-)-epicatechin + NADP+
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ANR1 or ANR2 converts cyanidin to a mixture of (+)-epicatechin and (-)-catechin, although in different proportions, indicating that both enzymes possess epimerase activity
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?
cyanidin + NADPH + H+
(-)-epicatechin + NADP+
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changes in the concentration of products and coenzyme in the ANR assay are determined by thin layer chromatography (TLC), HPLC, mass spectrometry (MS) and UV spectrophotometry
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?
cyanidin + NADPH + H+
(-)-epicatechin + NADP+
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?
delphinidin + 2 NADPH + H+
(-)-epigallocatechin + 2 NADP+
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preference of anthocyanidin substrates in decreasing order: cyanidin, pelargonidin and delphinidin
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?
(2R,3R)-epigallocatechin + 2 NADP+
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?
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?
delphinidin + 2 NADPH + H+
(2R,3R)-epigallocatechin + 2 NADP+
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?
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?
delphinidin + 2 NADPH + H+
(2R,3R)-epigallocatechin + 2 NADP+
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?
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?
pelargonidin + 2 NADPH + H+
(-)-epiafzelechin + 2 NADP+
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24% activity compared to cyanidin
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?
pelargonidin + 2 NADPH + H+
(-)-epiafzelechin + 2 NADP+
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preference of anthocyanidin substrates in decreasing order: cyanidin, pelargonidin and delphinidin
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?
?
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(2R,3S)-epicatechin is also observed from the catalysis of recombinant CssANRa and CssANRb
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additional information
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(2R,3S)-epicatechin is also observed from the catalysis of recombinant CssANRa and CssANRb
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additional information
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(2R,3S)-epicatechin is also observed from the catalysis of recombinant CssANRa and CssANRb
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additional information
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(2R,3S)-epicatechin is also observed from the catalysis of recombinant CssANRa and CssANRb
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additional information
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substrate molecular docking analysis
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additional information
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the enzyme is unable to use delphinidin and perlargonidin as a substrate and does not use NADH as cosubstrate
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additional information
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the enzyme is unable to use delphinidin and perlargonidin as a substrate and does not use NADH as cosubstrate
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additional information
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recombinant enzyme ANR does not generate epicatechin from epicatechin-cysteine conjugate in hairy roots
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additional information
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Medicago truncatula ecotype R108
recombinant enzyme ANR does not generate epicatechin from epicatechin-cysteine conjugate in hairy roots
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additional information
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ANR converts cyanidin, delphinidin, and pelargonidin to their corresponding flavan-3-ols. Enzymatic products include 2S,3R-trans, 2R,3R-cis and probably 2S,3S-cis-flavan-3-ol isomers
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additional information
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ANR converts cyanidin, delphinidin, and pelargonidin to their corresponding flavan-3-ols. Enzymatic products include 2S,3R-trans, 2R,3R-cis and probably 2S,3S-cis-flavan-3-ol isomers
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?
additional information
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the recombinant protein in vitro converts anthocyanidins to 2R,3R-cis-flavan-3-ols and 2S,3R-trans-flavan-3-ols, two stereo configurations at the C2 and C3 positions, such as (-)-epicatechin and (-)-catechin. flavan-3-ols produced from the catalysis of Trx-VbANR result from the reduction activity of VbANR but not Trx. Stereochemistry of the enzyme reaction, overview
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additional information
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the recombinant protein in vitro converts anthocyanidins to 2R,3R-cis-flavan-3-ols and 2S,3R-trans-flavan-3-ols, two stereo configurations at the C2 and C3 positions, such as (-)-epicatechin and (-)-catechin. flavan-3-ols produced from the catalysis of Trx-VbANR result from the reduction activity of VbANR but not Trx. Stereochemistry of the enzyme reaction, overview
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