The C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivity.
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.
Turnbull
Jonathan J
JJ
The Oxford Centre for Molecular Sciences and The Dyson Perrins Laboratory, The Department of Chemistry, South Parks Road, Oxford OX1 3QY, UK.
Nagle
Michael J
MJ
Seibel
Jürgen F
JF
Welford
Richard W D
RW
Grant
Guy H
GH
Schofield
Christopher J
CJ
D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D003653:Decarboxylation; D005419:Flavonoids / Q000378:metabolism*; D008958:Models, Molecular; D008968:Molecular Conformation; D010105:Oxygenases / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity
D005419:Flavonoids; D010105:Oxygenases; C118159:anthocyanidin synthase; C001532:leucocyanidin