Stereochemistry of C-methylation in the biosynthesis of rhododendrin in Alnus and Betula |
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Authors: | Martina Klischies Meinhart H Zenk |
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Institution: | Lehrstuhl für Pflanzenphysiologie, Ruhr-Universität Bochum, D 4630 Bochum, West Germany |
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Abstract: | Using differently labelled precursors, it was established that rhododendrin (3-(4-hydroxyphenyl)-1-methylpropyl-β-D-glucopyranoside) is formed through the phenylpropane pathway via p-coumaryl alcohol, dihydro-p-coumaryl alcohol and C-methylation of the γ-C-atom of the C6C3 unit with methionine supplying the methyl group. It was demonstrated that the pro-(S)-hydrogen atom of dihydro-p-coumaryl alcohol is replaced stereospecifically by the methyl group. |
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Keywords: | Betulaceae cinnamic acid pathway stereochemistry rhododendrin phenylpropanoid |
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