15-Cis-phytoene desaturase

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15-cis-phytoene desaturase
Oryza-sativa-phytoene-desaturase-PDB-5mog.png
Crystallographic structure of a phytoene desaturase monomer from rice. [1]
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EC no. 1.3.5.5
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15-cis-phytoene desaturases (PDS, plant-type phytoene desaturases) (EC 1.3.5.5, 15-cis-phytoene:plastoquinone oxidoreductase), are enzymes involved in the carotenoid biosynthesis in plants and cyanobacteria. [2] Phytoene desaturases are membrane-bound enzymes localized in plastids and introduce two double bonds into their colorless substrate phytoene by dehydrogenation and isomerize two additional double bonds. [3] [4] This reaction starts a biochemical pathway involving three further enzymes (zeta-carotene isomerase, zeta-carotene desaturase and carotene cis-trans isomerase) called the poly-cis pathway and leads to the red colored lycopene. The homologous phytoene desaturase found in bacteria and fungi (CrtI) converts phytoene directly to lycopene by an all-trans pathway. [5]

Contents

Biochemistry

The conversion of phytoene to lycopene in plants and cyanobacteria (left) compared to bacteria and fungi(right). Phytoene desaturation PLOS ONE.png
The conversion of phytoene to lycopene in plants and cyanobacteria (left) compared to bacteria and fungi(right).

PDS converts 15-cis-phytoene into 9,15,9'-tri-cis-ζ-carotene through reduction of the enzymes non-covalently bound FAD cofactor. [6] This conversion introduces two additional double bonds at positions 11 and 11' of the carbon chain and isomerizes two adjacent already existing double bonds at positions 9 and 9' from trans to cis. The electrons involved in the reaction are subsequently transferred onto plastoquinone [7] and to plastid terminal oxidase PTOX ultimately coupling the desaturation to oxygen reduction. Disruption of this biosynthesis step results in albinism and stunted plant growth. [8]

Applications

Disruption of PDS function can be achieved by bleaching herbicides such as norflurazon [9] and fluridone. [10] These inhibitors occupy the binding pocket of plastoquinone within the enzyme thus blocking it from its function. [1] Due to the clear effect of PDS disruption in plants, the corresponding gene was targeted to showcase successful genome editing in fruit such as apples, [11] grapes [12] or bananas [13] using CRISPR/Cas9 systems. In rice, the natural PDS was supplemented by its bacterial homolog to create Golden Rice and thus increase the β-carotene content of the rice endosperm.

See also

Related Research Articles

<span class="mw-page-title-main">Lycopene</span> Carotenoid pigment

Lycopene is an organic compound classified as a tetraterpene and a carotene. Lycopene is a bright red carotenoid hydrocarbon found in tomatoes and other red fruits and vegetables.

<span class="mw-page-title-main">Carotenoid</span> Class of chemical compounds; yellow, orange or red plant pigments

Carotenoids are yellow, orange, and red organic pigments that are produced by plants and algae, as well as several bacteria, archaea, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, corn, tomatoes, canaries, flamingos, salmon, lobster, shrimp, and daffodils. Over 1,100 identified carotenoids can be further categorized into two classes – xanthophylls and carotenes.

<span class="mw-page-title-main">Astaxanthin</span> Chemical compound

Astaxanthin is a keto-carotenoid within a group of chemical compounds known as terpenes. Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups. It is a lipid-soluble pigment with red coloring properties, which result from the extended chain of conjugated double bonds at the center of the compound.

<span class="mw-page-title-main">Phytofluene</span> Chemical compound

Phytofluene is a colorless carotenoid found naturally in tomatoes and other vegetables. It is the second product of carotenoid biosynthesis. It is formed from phytoene in a desaturation reaction leading to the formation of five conjugated double bonds. In the following step, addition of carbon-carbon conjugated double bonds leads to the formation of z-carotene and appearance of visible color.

CRT is the gene cluster responsible for the biosynthesis of carotenoids. Those genes are found in eubacteria, in algae and are cryptic in Streptomyces griseus.

In enzymology, a carotene 7,8-desaturase (EC 1.14.99.30) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Damascenone</span> Chemical compound

Damascenones are a series of closely related chemical compounds that are components of a variety of essential oils. The damascenones belong to a family of chemicals known as rose ketones, which also includes damascones and ionones. beta-Damascenone is a major contributor to the aroma of roses, despite its very low concentration, and is an important fragrance chemical used in perfumery.

<span class="mw-page-title-main">Phytoene</span> Chemical compound

Phytoene is a 40-carbon intermediate in the biosynthesis of carotenoids. The synthesis of phytoene is the first committed step in the synthesis of carotenoids in plants. Phytoene is produced from two molecules of geranylgeranyl pyrophosphate (GGPP) by the action of the enzyme phytoene synthase. The two GGPP molecules are condensed together followed by removal of diphosphate and proton shift leading to the formation of phytoene.

Phytoene synthase is a transferase enzyme involved in the biosynthesis of carotenoids. It catalyzes the conversion of geranylgeranyl pyrophosphate to phytoene. This enzyme catalyses the following chemical reaction

9,9'-dicis-zeta-carotene desaturase is an enzyme with systematic name 9,9'-dicis-zeta-corotene:quinone oxidoreductase. This enzyme catalyses the following chemical reaction

4,4'-Diapophytoene desaturase is an enzyme with systematic name 15-cis-4,4'-diapophytoene:FAD oxidoreductase. This enzyme catalyses the following chemical reaction

All-trans-zeta-carotene desaturase is an enzyme with systematic name all-trans-zeta-carotene:acceptor oxidoreductase. This enzyme catalyses the following chemical reaction

Phytoene desaturase (neurosporene-forming) is an enzyme with systematic name 15-cis-phytoene:acceptor oxidoreductase (neurosporene-forming). This enzyme catalyses the following chemical reaction

Phytoene desaturase (zeta-carotene-forming) is an enzyme with systematic name 15-cis-phytoene:acceptor oxidoreductase (zeta-carotene-forming). This enzyme catalyses the following chemical reaction

Phytoene desaturase (3,4-didehydrolycopene-forming) is an enzyme with systematic name 15-cis-phytoene:acceptor oxidoreductase (3,4-didehydrolycopene-forming). This enzyme catalyses the following chemical reaction

<span class="mw-page-title-main">Phytoene desaturase (lycopene-forming)</span>

Phytoene desaturase (lycopene-forming) are enzymes found in archaea, bacteria and fungi that are involved in carotenoid biosynthesis. They catalyze the conversion of colorless 15-cis-phytoene into a bright red lycopene in a biochemical pathway called the poly-trans pathway. The same process in plants and cyanobacteria utilizes four separate enzymes in a poly-cis pathway.

ζ-Carotene isomerase is an enzyme with systematic name 9,15,9'-tricis-zeta-carotene cis-trans-isomerase. This enzyme catalyses the following chemical reaction

Prolycopene isomerase is an enzyme with systematic name 7,9,7',9'-tetracis-lycopene cis-trans-isomerase. This enzyme catalyses the following chemical reaction

Lycopene β-cyclase is an enzyme with systematic name carotenoid beta-end group lyase (decyclizing). This enzyme catalyses the following chemical reaction

Phytoene desaturase may refer to:

References

  1. 1 2 PDB: 5mog ​; Brausemann A, Gemmecker S, Koschmieder J, Ghisla S, Beyer P, Einsle O (August 2017). "Structure of Phytoene Desaturase Provides Insights into Herbicide Binding and Reaction Mechanisms Involved in Carotene Desaturation". Structure. 25 (8): 1222–1232.e3. doi: 10.1016/j.str.2017.06.002 . PMID   28669634.
  2. ↑ Fraser PD, Linden H, Sandmann G (May 1993). "Purification and reactivation of recombinant Synechococcus phytoene desaturase from an overexpressing strain of Escherichia coli". The Biochemical Journal. 291 ( Pt 3) (3): 687–92. doi:10.1042/bj2910687. PMC   1132422 . PMID   8489496.
  3. ↑ Schneider C, Böger P, Sandmann G (July 1997). "Phytoene desaturase: heterologous expression in an active state, purification, and biochemical properties". Protein Expression and Purification. 10 (2): 175–9. doi:10.1006/prep.1997.0730. PMID   9226712.
  4. ↑ Breitenbach J, Sandmann G (March 2005). "zeta-Carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene". Planta. 220 (5): 785–93. doi:10.1007/s00425-004-1395-2. PMID   15503129. S2CID   23793453.
  5. ↑ Moise AR, Al-Babili S, Wurtzel ET (31 October 2013). "Mechanistic aspects of carotenoid biosynthesis". Chemical Reviews. 114 (1): 164–193. doi:10.1021/cr400106y. PMC   3898671 . PMID   24175570.
  6. ↑ Gemmecker S, Schaub P, Koschmieder J, Brausemann A, Drepper F, Rodriguez-Franco M, Ghisla S, Warscheid B, Einsle O, Beyer P (July 2015). "Phytoene Desaturase from Oryza sativa: Oligomeric Assembly, Membrane Association and Preliminary 3D-Analysis". PLOS ONE. 10 (7): e0131717. Bibcode:2015PLoSO..1031717G. doi: 10.1371/journal.pone.0131717 . PMC   4492965 . PMID   26147209.
  7. ↑ Norris SR, Barrette TR, DellaPenna D (December 1995). "Genetic dissection of carotenoid synthesis in arabidopsis defines plastoquinone as an essential component of phytoene desaturation". The Plant Cell. 7 (12): 2139–49. doi:10.1105/tpc.7.12.2139. PMC   161068 . PMID   8718624.
  8. ↑ Qin G, Gu H, Ma L, Peng Y, Deng XW, Chen Z, Qu LJ (May 2007). "Disruption of phytoene desaturase gene results in albino and dwarf phenotypes in Arabidopsis by impairing chlorophyll, carotenoid, and gibberellin biosynthesis". Cell Research. 17 (5): 471–82. doi: 10.1038/cr.2007.40 . PMID   17486124.
  9. ↑ Breitenbach J, Zhu C, Sandmann G (November 2001). "Bleaching herbicide norflurazon inhibits phytoene desaturase by competition with the cofactors". Journal of Agricultural and Food Chemistry. 49 (11): 5270–2. doi:10.1021/jf0106751. PMID   11714315.
  10. ↑ Sandmann, Gerhard (2002). "2: Bleaching Herbicides: Action Mechanism in Carotenoid Biosynthesis, Structural Requirements and Engineering of Resistance". In Böger, Peter; Wakabayashi, Ko; Hirai, Kenji (eds.). Herbicide Classes in Development: Mode of Action, Targets, Genetic Engineering, Chemistry (1 ed.). Springer-Verlag Berlin Heidelberg. pp. 43–57. doi:10.1007/978-3-642-59416-8_2. ISBN   978-3-642-63972-2.
  11. ↑ Nishitani C, Hirai N, Komori S, Wada M, Okada K, Osakabe K, Yamamoto T, Osakabe Y (August 2016). "Efficient Genome Editing in Apple Using a CRISPR/Cas9 system". Scientific Reports. 6: 31481. Bibcode:2016NatSR...631481N. doi:10.1038/srep31481. PMC   4987624 . PMID   27530958.
  12. ↑ Nakajima I, Ban Y, Azuma A, Onoue N, Moriguchi T, Yamamoto T, Toki S, Endo M (May 2017). "CRISPR/Cas9-mediated targeted mutagenesis in grape". PLOS ONE. 12 (5): e0177966. Bibcode:2017PLoSO..1277966N. doi: 10.1371/journal.pone.0177966 . PMC   5436839 . PMID   28542349.
  13. ↑ Naim, Fatima; Dugdale, Benjamin; Kleidon, Jennifer; Brinin, Anthony; Shand, Kylie; Waterhouse, Peter; Dale, James (2018-07-09). "Gene editing the phytoene desaturase alleles of Cavendish banana using CRISPR/Cas9". Transgenic Research. 27 (5): 451–460. doi:10.1007/s11248-018-0083-0. ISSN   1573-9368. PMC   6156769 . PMID   29987710.


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