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Literature summary extracted from

  • Gargouri, M.; Chaudiere, J.; Manigand, C.; Mauge, C.; Bathany, K.; Schmitter, J.M.; Gallois, B.
    The epimerase activity of anthocyanidin reductase from Vitis vinifera and its regiospecific hydride transfers (2010), Biol. Chem., 391, 219-227.
    View publication on PubMed

Organism

EC Number Organism UniProt Comment Textmining
1.3.1.112 Vitis vinifera Q5FB34
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Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.3.1.112 2 cyanidin + 4 NADPH + 4 H+
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 Vitis vinifera (+)-epicatechin + (-)-catechin + 4 NADP+ at pH 7.5 and 30°C, the first hydride transfer to anthocyanidin is irreversible, and no intermediate is released during catalysis ir
1.3.1.112 2 delphinidin + 4 NADPH + 4 H+
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 Vitis vinifera (-)-gallocatechin + (+)-epigallocatechin + 4 NADP+
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 ir
1.3.1.112 2 pelargonidin + 4 NADPH + 4 H+
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 Vitis vinifera (-)-afzelechin + (+)-epiafzelechin + 4 NADP+
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 ir
1.3.1.112 additional information in the presence of excess NADP+, ANR acts as a flavan-3-ol C3-epimerase, but only with 2R-flavan-3-ols, not with 2S-flavan-3-ols produced by the enzyme in the forward reaction. C3-epimerization should be achieved by tautomerization between the two hydride transfers and this produces a quinone methide intermediate which serves as C4 target of the second hydride transfer, avoiding any stereospecific modification of carbon 3. The inversion of C2 stereochemistry required for reverse epimerization suggests that the 2S configuration induces an irreversible product dissociation Vitis vinifera ?
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 ?

Synonyms

EC Number Synonyms Comment Organism
1.3.1.112 ANR
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 Vitis vinifera