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Peridinin

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Peridinin
Skeletal formula
Skeletal formula
Names
IUPAC name Acetic acid heptan-1-yl]vinyl]-5-oxo-2-furylidene]-3,10-dimethylundeca-1,3,5,7,9-pentaenylidene]-3,5,5-trimethylcyclohexyl] ester
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • (/(C)=C/C=C/C=C/C=C(C)/C=C2C=C(/C=C/3(O4)4(C)C(O)CC(C)3C)C(O\2)=O)=C=C1(C)(O)C(OC(C)=O)CC(C)1C
Properties
Chemical formula C39H50O7
Molar mass 630.822 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Peridinin is a light-harvesting apocarotenoid, a pigment associated with chlorophyll and found in the peridinin-chlorophyll-protein (PCP) light-harvesting complex in dinoflagellates, best studied in Amphidinium carterae.

Biological significance

Crystal structure of the soluble peridinin-chlorophyll-protein complex from the photosynthetic dinoflagellate Amphidinium carterae. This complex is found in many photosynthetic dinoflagellates and involves a boat or cradle-shaped protein with two pseudosymmetrical repeats of eight alpha helices (shown in blue and orange) wrapped around a pigment-filled central cavity. Each eight-helix segment binds one chlorophyll molecule (green, with central magnesium ion shown as a green sphere), one diacylglycerol molecule (yellow) and four peridinin molecules (gray).

Peridinin is an apocarotenoid pigment that some organisms use in photosynthesis. Many photosynthetic dinoflagellates use peridinin, which absorbs blue-green light in the 470-550nm range, outside the range accessible to chlorophyll molecules. The peridinin-chlorophyll-protein complex is a specialized molecular complex consisting of a boat-shaped protein molecule with a large central cavity that contains peridinin, chlorophyll, and lipid molecules, usually in a 4:1 ratio of peridinin to chlorophyll.

Spectral characteristics

Emission and excitation spectra of Peridinin Chlorophyll (PerCP)
  • Absorption maximum: 483 nm
  • Emission maximum: 676 nm
  • Extinction coefficient (ε): 1.96 x 10Mcm
  • A483/A280 ≥ 4.6

Applications

Peridinin chlorophyll (PerCP) is commonly used in immunoassays such as fluorescence-activated cell sorting (FACS) and flow cytometry. The fluorophore is covalently linked to proteins or antibodies for use in research applications.

References

  1. ^ Hofmann, E; Wrench, PM; Sharples, FP; Hiller, RG; Welte, W; Diederichs, K (21 June 1996). "Structural basis of light harvesting by carotenoids: peridinin-chlorophyll-protein from Amphidinium carterae" (PDF). Science. 272 (5269): 1788–91. doi:10.1126/science.272.5269.1788. PMID 8650577.
  2. Schulte, Tim; Johanning, Silke; Hofmann, Eckhard (December 2010). "Structure and function of native and refolded peridinin-chlorophyll-proteins from dinoflagellates". European Journal of Cell Biology. 89 (12): 990–997. doi:10.1016/j.ejcb.2010.08.004. PMID 20846743.
  3. Jiang, Jing; Zhang, Hao; Kang, Yisheng; Bina, David; Lo, Cynthia S.; Blankenship, Robert E. (July 2012). "Characterization of the peridinin–chlorophyll a-protein complex in the dinoflagellate Symbiodinium". Biochimica et Biophysica Acta (BBA) - Bioenergetics. 1817 (7): 983–989. doi:10.1016/j.bbabio.2012.03.027. PMC 3947849. PMID 22497797.
  4. "Peridinin Chlorophyll (PerCP)". Archived from the original on 2016-04-23. Retrieved 2014-06-07.
Carotenoids
Carotenes (C40)
Xanthophylls (C40)
Apocarotenoids (C<40)
Vitamin A retinoids (C20)
Retinoid drugs
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