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15,9'-dicis-phytofluene + plastoquinone
9,15,9'-tricis-zeta-carotene + plastoquinol
15-cis-phytoene + 2 decyl-plastoquinone
9,15,9'-tricis-zeta-carotene + 2 decyl-plastoquinol
15-cis-phytoene + 2 decyl-ubiquinone
9,15,9'-tricis-zeta-carotene + 2 decyl-plastoquinol
-
this quinone derivative is used in the study because the natural C45-ubiquinone is not available commercially
-
-
?
15-cis-phytoene + 2 decylubiquinone
9,15,9'-tricis-zeta-carotene + 2 decyl-plastoquinol
-
this quinone derivative is used in the study because the natural C45-ubiquinone is not available commercially
-
-
?
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
15-cis-phytoene + 2,5-dibromo-3-methyl-6-isopropyl-1,4-benzoquinone
9,15,9'-tricis-zeta-carotene + 2,5-dibromo-3-methyl-6-isopropyl-1,4-benzoquinol
-
-
-
-
?
15-cis-phytoene + 5-n-undecyl-6-hydroxy-4,7-dioxobenzothiazole + H2O
9,15,9'-tricis-zeta-carotene + 5-n-undecyl-4,6,7-trihydroxybenzothiazole
-
-
-
-
?
15-cis-phytoene + acceptor
9,15,9'-tricis-zeta-carotene + reduced acceptor
15-cis-phytoene + duroquinone
9,15,9'-tricis-zeta-carotene + duroquinol
-
-
-
-
?
15-cis-phytoene + plastoquinone
15,9'-dicis-phytofluene + plastoquinol
15-cis-phytoene + plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
the biosynthetic pathway of carotenoid synthesis involves several steps of desaturation requiring free energy, for instance the transition from phytoene to phytofluene achieved by phytoene desaturase. This reaction is associated with a reduction of plastoquinone. The oxidation of the plastoquinol is then achieved by a plastoquinol:oxygen oxidoreductase. Might additionally mediate the reduction of plastoquinone by internal reductants
-
-
?
additional information
?
-
15,9'-dicis-phytofluene + plastoquinone
9,15,9'-tricis-zeta-carotene + plastoquinol
-
-
-
-
?
15,9'-dicis-phytofluene + plastoquinone
9,15,9'-tricis-zeta-carotene + plastoquinol
-
-
-
?
15,9'-dicis-phytofluene + plastoquinone
9,15,9'-tricis-zeta-carotene + plastoquinol
-
-
-
?
15,9'-dicis-phytofluene + plastoquinone
9,15,9'-tricis-zeta-carotene + plastoquinol
-
-
-
?
15-cis-phytoene + 2 decyl-plastoquinone
9,15,9'-tricis-zeta-carotene + 2 decyl-plastoquinol
-
this quinone derivative is used in the study because the natural C45-plastoquinone is not available commercially. Decyl-plastoquinone is very effective as a cofactor of desaturation. The simultanous presence of NADP+ has no influence on the activity
-
-
?
15-cis-phytoene + 2 decyl-plastoquinone
9,15,9'-tricis-zeta-carotene + 2 decyl-plastoquinol
-
-
-
?
15-cis-phytoene + 2 decyl-plastoquinone
9,15,9'-tricis-zeta-carotene + 2 decyl-plastoquinol
-
this quinone derivative is used in the study because the natural C45-plastoquinone is not available commercially
-
-
?
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
phytoene desaturase is an early enzyme of the carotenoid biosynthetic pathway
-
-
?
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
overall reaction
-
-
?
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
overall reaction. The conversion rate with all-trans-phytoene is 10% of the value with the 15-cis isomer
-
-
?
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
-
-
-
?
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
the biosynthetic pathway of carotenoid synthesis involves several steps of desaturation requiring free energy, for instance the transition from phytoene to phytofluene achieved by phytoene desaturase. This reaction is associated with a reduction of plastoquinone. The oxidation of the plastoquinol is then achieved by a plastoquinol:oxygen oxidoreductase. Might additionally mediate the reduction of plastoquinone by internal reductants
-
-
?
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
-
-
-
?
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
-
-
-
?
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
-
-
-
?
15-cis-phytoene + acceptor
9,15,9'-tricis-zeta-carotene + reduced acceptor
phytoene desaturase is an enzyme of the carotenoid biosynthetic pathway
-
-
?
15-cis-phytoene + acceptor
9,15,9'-tricis-zeta-carotene + reduced acceptor
-
-
-
?
15-cis-phytoene + acceptor
9,15,9'-tricis-zeta-carotene + reduced acceptor
phytoene desaturase is an early enzyme of the carotenoid biosynthetic pathway
-
-
?
15-cis-phytoene + acceptor
9,15,9'-tricis-zeta-carotene + reduced acceptor
-
-
-
-
?
15-cis-phytoene + acceptor
9,15,9'-tricis-zeta-carotene + reduced acceptor
-
phytoene desaturase is an early enzyme of the carotenoid biosynthetic pathway
-
-
?
15-cis-phytoene + acceptor
9,15,9'-tricis-zeta-carotene + reduced acceptor
-
-
-
-
?
15-cis-phytoene + acceptor
9,15,9'-tricis-zeta-carotene + reduced acceptor
-
-
-
?
15-cis-phytoene + acceptor
9,15,9'-tricis-zeta-carotene + reduced acceptor
phytoene desaturase is an enzyme of the carotenoid biosynthetic pathway
-
-
?
15-cis-phytoene + plastoquinone
15,9'-dicis-phytofluene + plastoquinol
-
-
-
-
?
15-cis-phytoene + plastoquinone
15,9'-dicis-phytofluene + plastoquinol
-
-
-
?
15-cis-phytoene + plastoquinone
15,9'-dicis-phytofluene + plastoquinol
-
-
-
?
15-cis-phytoene + plastoquinone
15,9'-dicis-phytofluene + plastoquinol
-
-
-
?
15-cis-phytoene + plastoquinone
15,9'-dicis-phytofluene + plastoquinol
decyl-plastoquinone is used for enzyme assays
-
-
?
additional information
?
-
geranylgeranyl diphosphate is catalysed by phytoene synthase and phytoene desaturase to phytoene and phytofluene, respectively. The subsequent steps involve desaturation, isomerisation and cyclisation reactions to form alpha- and beta-carotene stereoisomers, via all-trans lycopene
-
-
-
additional information
?
-
geranylgeranyl diphosphate is catalysed by phytoene synthase and phytoene desaturase to phytoene and phytofluene, respectively. The subsequent steps involve desaturation, isomerisation and cyclisation reactions to form alpha- and beta-carotene stereoisomers, via all-trans lycopene
-
-
-
additional information
?
-
-
no activity with NADP+
-
-
?
additional information
?
-
benzoquinone cosubstrates are strongly preferred over naphthoquinones
-
-
?
additional information
?
-
PDS requires plastoquinone as a directly interacting co-substrate to reoxidize the enzyme-bound FADred formed upon desaturation. The enzyme structure has led to the conclusion that both lipophilic substrates are bound inside the same substrate cavity that cannot be occupied by both simultaneously. The central 15-cis configuration of phytoene mediates the regiospecificity in catalysis, overview. LC-MS analysis of PDS desaturation products produced from asymmetric (C35) 15-cis-norphytoene
-
-
-
additional information
?
-
-
the enzyme also shows activity with NADP+ as cosubstrate, the affinity for NADP+ is lower than for decylplastoquinone or decylubioquinone
-
-
?
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15,9'-dicis-phytofluene + plastoquinone
9,15,9'-tricis-zeta-carotene + plastoquinol
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
15-cis-phytoene + acceptor
9,15,9'-tricis-zeta-carotene + reduced acceptor
15-cis-phytoene + plastoquinone
15,9'-dicis-phytofluene + plastoquinol
15-cis-phytoene + plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
the biosynthetic pathway of carotenoid synthesis involves several steps of desaturation requiring free energy, for instance the transition from phytoene to phytofluene achieved by phytoene desaturase. This reaction is associated with a reduction of plastoquinone. The oxidation of the plastoquinol is then achieved by a plastoquinol:oxygen oxidoreductase. Might additionally mediate the reduction of plastoquinone by internal reductants
-
-
?
additional information
?
-
15,9'-dicis-phytofluene + plastoquinone
9,15,9'-tricis-zeta-carotene + plastoquinol
-
-
-
-
?
15,9'-dicis-phytofluene + plastoquinone
9,15,9'-tricis-zeta-carotene + plastoquinol
-
-
-
?
15,9'-dicis-phytofluene + plastoquinone
9,15,9'-tricis-zeta-carotene + plastoquinol
-
-
-
?
15,9'-dicis-phytofluene + plastoquinone
9,15,9'-tricis-zeta-carotene + plastoquinol
-
-
-
?
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
phytoene desaturase is an early enzyme of the carotenoid biosynthetic pathway
-
-
?
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
overall reaction
-
-
?
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
the biosynthetic pathway of carotenoid synthesis involves several steps of desaturation requiring free energy, for instance the transition from phytoene to phytofluene achieved by phytoene desaturase. This reaction is associated with a reduction of plastoquinone. The oxidation of the plastoquinol is then achieved by a plastoquinol:oxygen oxidoreductase. Might additionally mediate the reduction of plastoquinone by internal reductants
-
-
?
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
-
-
-
?
15-cis-phytoene + 2 plastoquinone
9,15,9'-tricis-zeta-carotene + 2 plastoquinol
-
-
-
-
?
15-cis-phytoene + acceptor
9,15,9'-tricis-zeta-carotene + reduced acceptor
phytoene desaturase is an early enzyme of the carotenoid biosynthetic pathway
-
-
?
15-cis-phytoene + acceptor
9,15,9'-tricis-zeta-carotene + reduced acceptor
-
phytoene desaturase is an early enzyme of the carotenoid biosynthetic pathway
-
-
?
15-cis-phytoene + acceptor
9,15,9'-tricis-zeta-carotene + reduced acceptor
phytoene desaturase is an enzyme of the carotenoid biosynthetic pathway
-
-
?
15-cis-phytoene + plastoquinone
15,9'-dicis-phytofluene + plastoquinol
-
-
-
-
?
15-cis-phytoene + plastoquinone
15,9'-dicis-phytofluene + plastoquinol
-
-
-
?
15-cis-phytoene + plastoquinone
15,9'-dicis-phytofluene + plastoquinol
-
-
-
?
15-cis-phytoene + plastoquinone
15,9'-dicis-phytofluene + plastoquinol
-
-
-
?
additional information
?
-
geranylgeranyl diphosphate is catalysed by phytoene synthase and phytoene desaturase to phytoene and phytofluene, respectively. The subsequent steps involve desaturation, isomerisation and cyclisation reactions to form alpha- and beta-carotene stereoisomers, via all-trans lycopene
-
-
-
additional information
?
-
geranylgeranyl diphosphate is catalysed by phytoene synthase and phytoene desaturase to phytoene and phytofluene, respectively. The subsequent steps involve desaturation, isomerisation and cyclisation reactions to form alpha- and beta-carotene stereoisomers, via all-trans lycopene
-
-
-
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additional information
using the crystal structure of Oryza sativa PDS in complex with norflurazon, the relevance of homotetrameric assembly of the enzyme observed in crystallo is determined by dynamic mathematical modeling of reaction time courses, substrate channeling occurs of the intermediate phytofluene between individual subunits at membrane surfaces
malfunction
both the albino and dwarf phenotypes of the pds3 mutant result from functional disruption of the PDS3 gene. Chloroplast development is arrested at the proplastid stage in the pds3 mutant. Further analysis shows that a high level of phytoene is accumulated in the pds3 mutant. Disrupting PDS3 gene results in gene expression changes involved in at least 20 metabolic pathways, including the inhibition of many genes in carotenoid, chlorophyll, and GA biosynthesis pathways. The accumulated phytoene in the pds3 mutant might play an important role in certain negative feedbacks to affect gene expression of diverse cellular pathways
malfunction
high light stress, red light stress, or use of a phytoene desaturase inhibitor or a mitotic disrupter herbicide lead to the accumulation of 15-cis phytoene but not all-trans phytoene. Bleaching herbicides such as norflurazon are known to boost phytoene accumulation in the cells of Dunaliella salina and other higher plants, by inhibiting PDS, which prevents the conversion of phytoene to phytofluene
malfunction
-
high light stress, red light stress, or use of a phytoene desaturase inhibitor or a mitotic disrupter herbicide lead to the accumulation of 15-cis phytoene but not all-trans phytoene. Bleaching herbicides such as norflurazon are known to boost phytoene accumulation in the cells of Dunaliella salina and other higher plants, by inhibiting PDS, which prevents the conversion of phytoene to phytofluene
-
metabolism
maize phytoene desaturase and zeta-carotene desaturase catalyse a poly-Z desaturation pathway to the predominate geometric isomer 7,9,7',9'-tetra-Z-lycopene (poly-Z-lycopene or prolycopene), and not the all-trans substrate required by the downstream lycopene cyclase enzymes
metabolism
determination of the phytoene isomers in Dunaliella salina by NMR spectrocopy and analysis of the carotenoid synthesis pathway of Dunaliella salina, overview
metabolism
-
determination of the phytoene isomers in Dunaliella salina by NMR spectrocopy and analysis of the carotenoid synthesis pathway of Dunaliella salina, overview
-
physiological function
-
phytoene desaturase is an early enzyme of the carotenoid biosynthetic pathway
physiological function
-
phytoene desaturase is an early enzyme of the carotenoid biosynthetic pathway
physiological function
phytoene desaturase is an enzyme of the carotenoid biosynthetic pathway
physiological function
-
the enzyme is involved in carotenoid biosynthesis
physiological function
-
the enzyme is involved in carotenoid biosynthesis
physiological function
three functional units, comprising genes PSY1, PDS/ZISO, and ZDS/CrtISO, are responsible for the synthesis of 15-cis-phytoene, 9,9'-di-cis-zeta-carotene, and all-trans-lycopene, respectively. Silencing of desaturase PDS results in the induction of the isomerase in the same functional unit, ZISO. PDS-silenced fruits show a 55% reduction of total carotenoids, with phytoene and phytofluene being the most abundant compounds. All-trans-zeat-carotene is detectable in nonsilenced fruits
physiological function
upon transfer to high light, the transcript levels of all investigated carotenogenic genes including those coding for phytoene synthase, phytoene desaturase and both ketolases are increased
physiological function
carotenoids comprise a diverse range of naturally occurring stereoisomers, which differ in their physico-chemical properties. Their biosynthesis begins with phytoene, which is a rarity among carotenoids because it is colourless. Geranylgeranyl diphosphate is catalysed by phytoene synthase and phytoene desaturase to phytoene and phytofluene, respectively. The subsequent steps involve desaturation, isomerisation and cyclisation reactions to form alpha- and beta-carotene stereoisomers, via all-trans lycopene. The marine microalga Dunaliella salina is the richest source of beta-carotene, but it can accumulate phytoene and phytofluene as well. Dunaliella salina, similar to tomato, produces predominantly 15-cis phytoene isomer (over 98%) and a trace amount of all-trans phytoene (below 2%). 9-cis phytoene is not detected in any of the extracts of Dunaliella salina biomass. 15-cis phytoene is the most abundant isomer in Dunaliella salina and that it is subject to a series of isomerisation and desaturation reactions to form all-trans and 9-cis beta-carotene
physiological function
phytoene desaturase (PDS) is an essential plant carotenoid biosynthetic enzyme. PDS catalyzes the introduction of two double bonds into 15-cis-phytoene, yielding 9,15,9'-tri-cis-zeta-carotene via the intermediate 9,15-di-cis-phytofluene
physiological function
-
carotenoids comprise a diverse range of naturally occurring stereoisomers, which differ in their physico-chemical properties. Their biosynthesis begins with phytoene, which is a rarity among carotenoids because it is colourless. Geranylgeranyl diphosphate is catalysed by phytoene synthase and phytoene desaturase to phytoene and phytofluene, respectively. The subsequent steps involve desaturation, isomerisation and cyclisation reactions to form alpha- and beta-carotene stereoisomers, via all-trans lycopene. The marine microalga Dunaliella salina is the richest source of beta-carotene, but it can accumulate phytoene and phytofluene as well. Dunaliella salina, similar to tomato, produces predominantly 15-cis phytoene isomer (over 98%) and a trace amount of all-trans phytoene (below 2%). 9-cis phytoene is not detected in any of the extracts of Dunaliella salina biomass. 15-cis phytoene is the most abundant isomer in Dunaliella salina and that it is subject to a series of isomerisation and desaturation reactions to form all-trans and 9-cis beta-carotene
-
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Mayer, M.P.; Beyer, P.; Kleinig, H.
Quinone compounds are able to replace molecular oxygen as terminal electron acceptor in phytoene desaturation in chromoplasts of Narcissus pseudonarcissus L.
Eur. J. Biochem.
191
359-363
1990
Narcissus pseudonarcissus
brenda
Matthews, P.D.; Luo, R.; Wurtzel, E.T.
Maize phytoene desaturase and zeta-carotene desaturase catalyse a poly-Z desaturation pathway: implications for genetic engineering of carotenoid content among cereal crops
J. Exp. Bot.
54
2215-2230
2003
Zea mays (P49086)
brenda
Breitenbach, J.; Sandmann, G.
zeta-Carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene
Planta
220
785-793
2005
Capsicum annuum
brenda
Steinbrenner, J.; Sandmann, G.
Transformation of the green alga Haematococcus pluvialis with a phytoene desaturase for accelerated astaxanthin biosynthesis
Appl. Environ. Microbiol.
72
7477-7484
2006
Haematococcus lacustris
brenda
Kita, M.; Komatsu, A.; Omura, M.; Yano, M.; Ikoma, Y.; Moriguchi, T.
Cloning and expression of CitPDS1, a gene encoding phytoene desaturase in citrus
Biosci. Biotechnol. Biochem.
65
1424-1428
2001
Citrus unshiu (Q7GCA8)
brenda
Qin, G.; Gu, H.; Ma, L.; Peng, Y.; Deng, X.W.; Chen, Z.; Qu, L.J.
Disruption of phytoene desaturase gene results in albino and dwarf phenotypes in Arabidopsis by impairing chlorophyll, carotenoid, and gibberellin biosynthesis
Cell Res.
17
471-482
2007
Arabidopsis thaliana (Q07356)
brenda
Nievelstein, V.; Vandekerchove, J.; Tadros, M.H.; Lintig, J.V.; Nitschke, W.; Beyer, P.
Carotene desaturation is linked to a respiratory redox pathway in Narcissus pseudonarcissus chromoplast membranes. Involvement of a 23-kDa oxygen-evolving-complex-like protein
Eur. J. Biochem.
233
864-872
1995
Narcissus pseudonarcissus
brenda
Sandmann, G.; Mitchell, G.
In vitro inhibition studies of phytoene desaturase by bleaching ketomorpholine derivatives
J. Agric. Food Chem.
49
138-141
2001
Synechococcus sp.
brenda
Breitenbach, J.; Zhu, C.; Sandmann, G.
Bleaching herbicide norflurazon inhibits phytoene desaturase by competition with the cofactors
J. Agric. Food Chem.
49
5270-5272
2001
Synechococcus sp., Gentiana lutea
brenda
Ohki, S.; Miller-Sulger, R.; Wakabayashi, K.; Pfleiderer, W.; Bger, P.
Phytoene desaturase inhibition by O-(2-phenoxy)ethyl-N-aralkylcarbamates
J. Agric. Food Chem.
51
3049-3055
2003
Synechococcus elongatus PCC 7942 = FACHB-805
brenda
Zhu, Y.H.; Jiang, J.G.; Yan, Y.; Chen, X.W.
Isolation and characterization of phytoene desaturase cDNA involved in the beta-carotene biosynthetic pathway in Dunaliella salina
J. Agric. Food Chem.
53
5593-5597
2005
Dunaliella salina (Q3ZDQ0)
brenda
Cong, L.; Wang, C.; Li, Z.; Chen, L.; Yang, G.; Wang, Y.; He, G.
cDNA cloning and expression analysis of wheat (Triticum aestivum L.) phytoene and zeta-carotene desaturase genes
Mol. Biol. Rep.
37
3351-3361
2010
Triticum aestivum (B8YDB8)
brenda
Bennoun, P.
The present model for chlororespiration
Photosynth. Res.
73
273-277
2002
Embryophyta, Rhodophyta
brenda
Lopez, A.B.; Yang, Y.; Thannhauser, T.W.; Li, L.
Phytoene desaturase is present in a large protein complex in the plastid membrane
Physiol. Plant.
133
190-198
2008
Brassica oleracea (B2X8P6)
brenda
Arias, R.S.; Dayan, F.E., Michel, A.; Howell, J.; Scheffler, B.E.
Characterization of a higher plant herbicide-resistant phytoene desaturase and its use as a selectable marker
Plant Biotechnol. J.
4
263-273
2006
Hydrilla verticillata
brenda
Norris, S.R.; Barrette, T.R.; DellaPenna, D.
Genetic dissection of carotenoid synthesis in arabidopsis defines plastoquinone as an essential component of phytoene desaturation
Plant Cell
7
2139-2149
1995
Arabidopsis thaliana
brenda
Al-Babili, S.; von Lintig, J.; Haubruck, H.; Beyer, P.
A novel, soluble form of phytoene desaturase from Narcissus pseudonarcissus chromoplasts is Hsp70-complexed and competent for flavinylation, membrane association and enzymatic activation
Plant J.
9
601-612
1996
Narcissus pseudonarcissus
brenda
Li, Z.H.; Matthews, P.D.; Burr, B.; Wurtzel, E.T.
Cloning and characterization of a maize cDNA encoding phytoene desaturase, an enzyme of the carotenoid biosynthetic pathway
Plant Mol. Biol.
30
269-279
1996
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