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

Symplectic ID
32512
Source
PubMed
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Saturday, 5 September, 2026 - 18:43
DOI
10.1016/s0960-894x(03)00711-x
Publication Date
Monday, 3 November, 2003
First Page
3853
Last Page
3857
Keywords
Chromatography, High Pressure Liquid
Crystallography, X-Ray
Decarboxylation
Flavonoids
Models, Molecular
Molecular Conformation
Oxygenases
Stereoisomerism
Substrate Specificity
Authors
Turnbull, JJ
Nagle, MJ
Seibel, JF
Welford, RWD
Grant, GH
Schofield, CJ
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Abstract
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.
ISSN
0960-894X
Journal Title
Bioorg Med Chem Lett
Volume
13
Issue
21
ID at Source
14552794
Publication Status
Published
Open access
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