The C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivity.

Journal article

Anthocyanidin synthase (ANS), an iron(II) and 2-oxoglutarate (2OG) dependent oxygenase, catalyses the penultimate step in anthocyanin biosynthesis by oxidation of the 2R,3S,4S-cis-leucoanthocyanidins. It has been believed that in vivo the products of ANS are the anthocyanidins. However, in vitro studies on ANS using optically active cis- and trans-leucocyanidin substrates identified cyanidin as only a minor product; instead both quercetin and dihydroquercetin are products with the distribution being dependent on the C-4 stereochemistry of the leucocyanidin substrates.

Authors: Turnbull, J; Nagle, M; Seibel, J; Welford, R; Grant, G

• Publication status: Published
• Journal: Bioorganic and medicinal chemistry letters
• Volume: 13
• Issue: 21
• Pages: 3853-3857
• Publication date: 2003-11-01
• DOI: 10.1016/s0960-894x(03)00711-x
• EISSN: 1464-3405
• ISSN: 0960-894X
• Language: English
• Keywords: Molecular Conformation; Flavonoids; Substrate Specificity; Decarboxylation; Crystallography, X-Ray; Chromatography, High Pressure Liquid; Oxygenases; Stereoisomerism; Models, Molecular