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

2.50
Hdl Handle:
http://hdl.handle.net/10547/294532
Title:
The C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivity
Authors:
Turnbull, Jonathan J.; Nagle, Michael J.; Seibel, Jürgen F.; Welford, Richard W.D.; Grant, Guy H.; Schofield, Christopher J.
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.
Citation:
Turnbull, J.J., Nagle, M.J., Seibel, J.F., Welford, R.W.D., Grant, G.H. and Schofield, C.J. (2003) 'The C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivity', Bioorganic & Medicinal Chemistry Letters, 13(21),pp.3853-3857.
Publisher:
Elsevier
Journal:
Bioorganic & Medicinal Chemistry Letters
Issue Date:
2003
URI:
http://hdl.handle.net/10547/294532
DOI:
10.1016/S0960-894X(03)00711-X
Additional Links:
http://linkinghub.elsevier.com/retrieve/pii/S0960894X0300711X
Type:
Article
Language:
en
ISSN:
0960894X
Appears in Collections:
Cell and Cryobiology Research Group

Full metadata record

DC FieldValue Language
dc.contributor.authorTurnbull, Jonathan J.en_GB
dc.contributor.authorNagle, Michael J.en_GB
dc.contributor.authorSeibel, Jürgen F.en_GB
dc.contributor.authorWelford, Richard W.D.en_GB
dc.contributor.authorGrant, Guy H.en_GB
dc.contributor.authorSchofield, Christopher J.en_GB
dc.date.accessioned2013-06-25T15:36:40Z-
dc.date.available2013-06-25T15:36:40Z-
dc.date.issued2003-
dc.identifier.citationTurnbull, J.J., Nagle, M.J., Seibel, J.F., Welford, R.W.D., Grant, G.H. and Schofield, C.J. (2003) 'The C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivity', Bioorganic & Medicinal Chemistry Letters, 13(21),pp.3853-3857.en_GB
dc.identifier.issn0960894X-
dc.identifier.doi10.1016/S0960-894X(03)00711-X-
dc.identifier.urihttp://hdl.handle.net/10547/294532-
dc.description.abstractAnthocyanidin 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.en_GB
dc.language.isoenen
dc.publisherElsevieren_GB
dc.relation.urlhttp://linkinghub.elsevier.com/retrieve/pii/S0960894X0300711Xen_GB
dc.rightsArchived with thanks to Bioorganic & Medicinal Chemistry Lettersen_GB
dc.titleThe C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivityen
dc.typeArticleen
dc.identifier.journalBioorganic & Medicinal Chemistry Lettersen_GB
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