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Fig 1.

Two possible routes from dihydroflavonol to anthocyanidin.

2-Flaven-3,4-diol has not been isolated because of its instability under acidic conditions. (2R, 3S, 4S)-cis-Leucoanthocyanidine was confirmed to be the enzymatic product of DFR and to act as a substrate of ANS.

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Fig 1 Expand

Fig 2.

Two possible routes from dihydroflavonol to anthocyanidin.

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Fig 2 Expand

Fig 3.

Calculation results for conversion of dihydroflavonol (CP1) to 2-flaven-3,4-diol (CP4-1) via route B in a neutral aqueous environment.

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Fig 3 Expand

Fig 4.

The effect of 2-hydroxyl group on the A ring: conversion of 5,7-dehydroxydihydroflavonol (CP1’) to 3-oxo-flavan-4-ol (CP3-1’).

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Fig 4 Expand

Fig 5.

Calculation results for the late stage of the biosynthesis of anthocyanidin in a neutral aqueous environment.

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Fig 5 Expand