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Title:
ζ-Carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene | Planta
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The plant carotenoid biosynthetic pathway to cyclic carotenes proceeds via carotene precursors in cis configuration. Involvement of individual isomers was elucidated by genetic complementation of desaturations and in vitro reactions of the corresponding enzyme. Determination of substrate and product specificity of phytoene and ζ-carotene desaturase revealed that 15-cis-phytoene is converted to 9,15,9′-tricis-ζ-carotene with 15,9′-dicis-phytofluene as intermediate by the first desaturase. Prior to a subsequent conversion by ζ-carotene desaturase, the 15-cis double bond of 9,15,9′-tricis-ζ-carotene has to be (photo)isomerized to all-trans. Then, the resulting 9,9′-dicis-ζ-carotene is utilized by ζ-carotene desaturase via 7,9,9′-tricis-neurosporene to 7,9,7′,9′-tetracis-lycopene. Other ζ-carotene isomers that are assumed to be spontaneous isomerization products were not converted, except for the asymmetric 9-cis-ζ-carotene. This isomer is desaturated only to 7,9-dicis-neurosporene resembling a dead-end of the pathway. Prolycopene, the product of the desaturation reactions, is finally isomerized by a specific isomerase to all-trans-lycopene, which is a prerequisite for cyclization to β-carotene. The 5-cis-lycopene and the 9-cis-and 13-cis-β-carotene isomers detected in leaves are thought to originate independently from cis precursors by non-enzymatic isomerization of their all-trans forms.
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Keywords {🔍}
google, scholar, article, cas, sandmann, pubmed, ζcarotene, desaturase, plant, phytoene, carotenoid, chem, isomers, carotene, pathway, breitenbach, carotenoids, biochem, cis, products, lycopene, privacy, cookies, content, polycis, prolycopene, desaturation, isomerase, access, biosynthesis, expression, gene, soc, publish, search, biosynthetic, isomerization, tomato, related, cloning, essential, data, information, log, journal, research, planta, gerhard, reactions, discover,
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13-cis-β-carotene isomers detected month download article/chapter poly-cis carotene pathway ζ-carotene cis isomers ζ-carotene desaturase revealed asymmetric 9-cis-ζ-carotene poly-z-isomeric carotenoids c30-bounded stationary phase scenedesmus mutant c-6d poly-cis pathway ζ-carotene desaturase ζ-carotene isomers article planta aims cyanobacterium synechocystis sp 9′-tricis-ζ-carotene 9′-dicis-ζ-carotene full article pdf tetra-cis carotene phytoene desaturase diversification ζ-carotene accumulation privacy choices/manage cookies gentiana lutea article breitenbach 15-cis double bond carotene patterns derives lycopene isomers synthesized related subjects carotenoid biochemistry carotene isomerase involved isomeric β-carotenes engineered stationary phases ζ-carotene check access instant access trans carotene isomerization european economic area variable chain length uv/visible spectroscopy naturally occurring stereoisomer conditions privacy policy truncated gene products capsicum annuum cyclic carotenes proceeds spontaneous isomerization products phytoene desaturase combined hplc-ms tomato cdna coding prolamellar body formation gerhard sandmann carotenoid isomers
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headline:ζ-Carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene
description:The plant carotenoid biosynthetic pathway to cyclic carotenes proceeds via carotene precursors in cis configuration. Involvement of individual isomers was elucidated by genetic complementation of desaturations and in vitro reactions of the corresponding enzyme. Determination of substrate and product specificity of phytoene and ζ-carotene desaturase revealed that 15-cis-phytoene is converted to 9,15,9′-tricis-ζ-carotene with 15,9′-dicis-phytofluene as intermediate by the first desaturase. Prior to a subsequent conversion by ζ-carotene desaturase, the 15-cis double bond of 9,15,9′-tricis-ζ-carotene has to be (photo)isomerized to all-trans. Then, the resulting 9,9′-dicis-ζ-carotene is utilized by ζ-carotene desaturase via 7,9,9′-tricis-neurosporene to 7,9,7′,9′-tetracis-lycopene. Other ζ-carotene isomers that are assumed to be spontaneous isomerization products were not converted, except for the asymmetric 9-cis-ζ-carotene. This isomer is desaturated only to 7,9-dicis-neurosporene resembling a dead-end of the pathway. Prolycopene, the product of the desaturation reactions, is finally isomerized by a specific isomerase to all-trans-lycopene, which is a prerequisite for cyclization to β-carotene. The 5-cis-lycopene and the 9-cis-and 13-cis-β-carotene isomers detected in leaves are thought to originate independently from cis precursors by non-enzymatic isomerization of their all-trans forms.
datePublished:2004-10-21T00:00:00Z
dateModified:2004-10-21T00:00:00Z
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Capsicum
ζ-Carotene desaturase
ζ-Carotene isomers
Gentiana
Poly-cis carotenoids
Phytoene desaturase
Plant Sciences
Agriculture
Ecology
Forestry
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headline:ζ-Carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene
description:The plant carotenoid biosynthetic pathway to cyclic carotenes proceeds via carotene precursors in cis configuration. Involvement of individual isomers was elucidated by genetic complementation of desaturations and in vitro reactions of the corresponding enzyme. Determination of substrate and product specificity of phytoene and ζ-carotene desaturase revealed that 15-cis-phytoene is converted to 9,15,9′-tricis-ζ-carotene with 15,9′-dicis-phytofluene as intermediate by the first desaturase. Prior to a subsequent conversion by ζ-carotene desaturase, the 15-cis double bond of 9,15,9′-tricis-ζ-carotene has to be (photo)isomerized to all-trans. Then, the resulting 9,9′-dicis-ζ-carotene is utilized by ζ-carotene desaturase via 7,9,9′-tricis-neurosporene to 7,9,7′,9′-tetracis-lycopene. Other ζ-carotene isomers that are assumed to be spontaneous isomerization products were not converted, except for the asymmetric 9-cis-ζ-carotene. This isomer is desaturated only to 7,9-dicis-neurosporene resembling a dead-end of the pathway. Prolycopene, the product of the desaturation reactions, is finally isomerized by a specific isomerase to all-trans-lycopene, which is a prerequisite for cyclization to β-carotene. The 5-cis-lycopene and the 9-cis-and 13-cis-β-carotene isomers detected in leaves are thought to originate independently from cis precursors by non-enzymatic isomerization of their all-trans forms.
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Capsicum
ζ-Carotene desaturase
ζ-Carotene isomers
Gentiana
Poly-cis carotenoids
Phytoene desaturase
Plant Sciences
Agriculture
Ecology
Forestry
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