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

Guy Grant; Jonathan J. Turnbull; Michael J. Nagle; Jürgen F. Seibel; Richard W.D. Welford; Christopher J. Schofield

doi:10.1016/S0960-894X(03)00711-X

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

Guy Grant
, Jonathan J. Turnbull
, Michael J. Nagle
, Jürgen F. Seibel
, Richard W.D. Welford
, Christopher J. Schofield

Institute of Biomedical and Environmental Science & Technology (IBEST)

University of Oxford

Research output: Contribution to journal › Article › peer-review

38 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3853-3857
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	13
Issue number	21
DOIs	https://doi.org/10.1016/S0960-894X(03)00711-X
Publication status	Published - 1 Jan 2003

Keywords

biosynthesis

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title = "The C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivity",

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.",

keywords = "biosynthesis",

author = "Guy Grant and Turnbull, \{Jonathan J.\} and Nagle, \{Michael J.\} and Seibel, \{J{\"u}rgen F.\} and Welford, \{Richard W.D.\} and Schofield, \{Christopher J.\}",

year = "2003",

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doi = "10.1016/S0960-894X(03)00711-X",

language = "English",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - The C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivity

AU - Grant, Guy

AU - Turnbull, Jonathan J.

AU - Nagle, Michael J.

AU - Seibel, Jürgen F.

AU - Welford, Richard W.D.

AU - Schofield, Christopher J.

PY - 2003/1/1

Y1 - 2003/1/1

N2 - 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.

AB - 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.

KW - biosynthesis

U2 - 10.1016/S0960-894X(03)00711-X

DO - 10.1016/S0960-894X(03)00711-X

M3 - Article

SN - 0960-894X

VL - 13

SP - 3853

EP - 3857

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 21

ER -

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

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