Stereochemistry of C-methylation in the biosynthesis of rhododendrin in Alnus and Betula

Klischies, Martina und Zenk, Meinhart H. (1978): Stereochemistry of C-methylation in the biosynthesis of rhododendrin in Alnus and Betula. In: Phytochemistry, Bd. 17, Nr. 8: S. 1281-1284

Abstract

Using differently labelled precursors, it was established that rhododendrin (3-(4-hydroxyphenyl)-1-methylpropyl-β- -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 C6---C3 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.

• Dokumententyp: Zeitschriftenartikel
• Keywords: Betula alba; Alnus glutinosa; Betulaceae; cinnamic acid pathway; C-methylation; stereochemistry; rhododendrin; phenylpropanoid
• Fakultät: Chemie und Pharmazie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie