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Chemical Compound Review

Phycobilin     3-[2-[(Z)-[(5E)-3-(2- carboxyethyl)-5-[(4...

Synonyms: AC1O5PIT, 20298-86-6
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Disease relevance of Phycobilin


High impact information on Phycobilin

  • CpeS acts as a phycocyanobilin: Cys-beta84-phycobiliprotein lyase that can attach, in vitro and in vivo, phycocyanobilin (PCB) to cysteine-beta84 of the apo-beta-subunits of C-phycocyanin (CpcB) and phycoerythrocyanin (PecB) [5].
  • Analysis of the phycocyanin from a cpcE pseudo-revertant, which produced a near wild-type level of phycocyanin with alpha subunit carrying PCB, revealed a single amino acid substitution, alpha-Tyr129----Cys [6].
  • The unicellular rhodophyte, Porphyridium cruentum, and the filamentous cyanobacterium, Calothrix sp. PCC 7601, contain phycobiliproteins that have covalently bound phycobilin chromophores [7].
  • Biosynthesis of phycobilins. Ferredoxin-supported nadph-independent heme oxygenase and phycobilin-forming activities from Cyanidium caldarium [8].
  • A major component was a mesobiliverdin adduct, a previously described product of the in vitro reaction of PCB and apophycocyanin [6].

Chemical compound and disease context of Phycobilin


Biological context of Phycobilin

  • These observations provide strong support for inter-chromophore hetero energy transfer in mixed PEB/PCB dimers [10].
  • Contrary to phyA from Avena, the I700 intermediate from phyB reconstituted with either PCB or P phi B decayed following single exponential kinetics with a lifetime of 87 or 84 microseconds, respectively, at 10 degrees C. The formation of Pfr of PCB-containing recombinant phyB (phyB-PCB) could be fitted with three lifetimes of 9, 127, and 728 ms [11].
  • The coexistence of divergent groEL/cpn60 genes in different genomes in one cell offers insights into gene transfer from evolving chloroplasts to cell nuclei and convergent gene evolution in chlorophyll a/b versus chlorophyll a/c/phycobilin eukaryotic lineages [12].
  • Phylogenetic analysis of this region was largely consistent with that obtained from 16S rDNA sequence analysis and revealed a relationship between the primary PC DNA sequence and the phycobilin content of cells [13].
  • Seventy-five strains of oscillatorioid cyanobacteria were characterized by 16S rDNA sequence analysis, DNA base composition, DNA-DNA hybridization, fatty acid composition, phycobilin pigment composition, complementary chromatic adaptation, morphological characters, growth temperature and salinity tolerance [14].

Anatomical context of Phycobilin

  • Phylogenetic analysis of the plastid small-subunit ribosomal DNA (SSU rDNA) revealed that the Dinophysis mitra sequences are distantly related to those of phycobilin-containing Dinophysis species and are positioned within a lineage of haptophytes belonging to Prymnesiophyceae [15].
  • Both P phi B and PCB adducts of ASPHYA-ST were photoactive--the P phi B adduct displaying spectrophotometric properties nearly indistinguishable from those of the native photoreceptor, and the PCB adduct exhibiting blue-shifted absorption maxima [16].

Gene context of Phycobilin

  • When cells of a strain lacking PS I and chlL (coding for a polypeptide needed for light-independent protochlorophyllide reduction) were grown in darkness, the phycobilin and protochlorophyllide levels decreased upon deletion of scpB or scpE and the protoheme level was reduced in the strain lacking scpE [17].
  • Expression and characterization of cyanobacterium heme oxygenase, a key enzyme in the phycobilin synthesis. Properties of the heme complex of recombinant active enzyme [18].
  • (a) aphA was overexpressed in Escherichia coli with N-terminal His and S tags, and the protein was reconstituted by an optimized protocol with phycocyanobilin (PCB), to yield the photochromic chromoprotein, PCB-AphA, carrying the PCB chromophore [19].
  • These peptides were found to have the following sequences. alpha-1 PCB Cys(PCB)-Ala-Arg beta-2T PCB Ile-Thr-Gln-Gly-Asp-Cys(PCB)-Ser-Ala [2].
  • The formation of the Pfr state of the PCB adduct of Synechocystis phytochrome shows a deuterium effect similar as phyA (ca. 1.2) [3].

Analytical, diagnostic and therapeutic context of Phycobilin

  • In addition, a marine blue-green cryptomonad isolate was confirmed as Falcomonas daucoides by electron microscopy and phycobilin analysis so that it could be included in molecular sequence studies, since the original isolate is no longer available [20].
  • As there are many spectrally only slightly different tetrapyrroles in the extract, the triple-wavelength monitoring offered by the F/HPLC detector was inadequate for distinguishing between PCB and impurities [21].
  • Absorption, fluorescence and circular dichroism spectra indicate a major conformational change of the chromophore upon addition of the detergent, which probably controls the site selectivity of the addition reaction, and inhibits the oxidation of PCB to MBV [22].
  • Both subunits bind PCB, as assayed by Ni2+ affinity chromatography, SDS/PAGE and Zn2+-induced fluorescence [23].


  1. The relationship of a prochlorophyte Prochlorothrix hollandica to green chloroplasts. Turner, S., Burger-Wiersma, T., Giovannoni, S.J., Mur, L.R., Pace, N.R. Nature (1989) [Pubmed]
  2. Phycobiliprotein-bilin linkage diversity. I. Structural studies on A- and D-ring-linked phycocyanobilins. Bishop, J.E., Lagarias, J.C., Nagy, J.O., Schoenleber, R.W., Rapoport, H., Klotz, A.V., Glazer, A.N. J. Biol. Chem. (1986) [Pubmed]
  3. Raman spectroscopic and light-induced kinetic characterization of a recombinant phytochrome of the cyanobacterium Synechocystis. Remberg, A., Lindner, I., Lamparter, T., Hughes, J., Kneip, C., Hildebrandt, P., Braslavsky, S.E., Gärtner, W., Schaffner, K. Biochemistry (1997) [Pubmed]
  4. Chromophore incorporation, Pr to Pfr kinetics, and Pfr thermal reversion of recombinant N-terminal fragments of phytochrome A and B chromoproteins. Remberg, A., Ruddat, A., Braslavsky, S.E., Gärtner, W., Schaffner, K. Biochemistry (1998) [Pubmed]
  5. Chromophore attachment to phycobiliprotein beta-subunits: phycocyanobilin:cysteine-beta84 phycobiliprotein lyase activity of CpeS-like protein from Anabaena Sp. PCC7120. Zhao, K.H., Su, P., Li, J., Tu, J.M., Zhou, M., Bubenzer, C., Scheer, H. J. Biol. Chem. (2006) [Pubmed]
  6. Characterization of phycocyanin produced by cpcE and cpcF mutants and identification of an intergenic suppressor of the defect in bilin attachment. Swanson, R.V., Zhou, J., Leary, J.A., Williams, T., de Lorimier, R., Bryant, D.A., Glazer, A.N. J. Biol. Chem. (1992) [Pubmed]
  7. Phytochrome assembly. The structure and biological activity of 2(R),3(E)-phytochromobilin derived from phycobiliproteins. Cornejo, J., Beale, S.I., Terry, M.J., Lagarias, J.C. J. Biol. Chem. (1992) [Pubmed]
  8. Biosynthesis of phycobilins. Ferredoxin-supported nadph-independent heme oxygenase and phycobilin-forming activities from Cyanidium caldarium. Rhie, G., Beale, S.I. J. Biol. Chem. (1992) [Pubmed]
  9. Spectra of cells in flow cytometry using a vidicon detector. Wade, C.G., Rhyne, R.H., Woodruff, W.H., Bloch, D.P., Bartholomew, J.C. J. Histochem. Cytochem. (1979) [Pubmed]
  10. Dimerization and inter-chromophore distance of Cph1 phytochrome from Synechocystis, as monitored by fluorescence homo and hetero energy transfer. Otto, H., Lamparter, T., Borucki, B., Hughes, J., Heyn, M.P. Biochemistry (2003) [Pubmed]
  11. Recombinant type A and B phytochromes from potato. Transient absorption spectroscopy. Ruddat, A., Schmidt, P., Gatz, C., Braslavsky, S.E., Gärtner, W., Schaffner, K. Biochemistry (1997) [Pubmed]
  12. Ancient gene duplication and differential gene flow in plastid lineages: the GroEL/Cpn60 example. Wastl, J., Fraunholz, M., Zauner, S., Douglas, S., Maier, U.G. J. Mol. Evol. (1999) [Pubmed]
  13. Phylogenetic analyses of Synechococcus strains (cyanobacteria) using sequences of 16S rDNA and part of the phycocyanin operon reveal multiple evolutionary lines and reflect phycobilin content. Robertson, B.R., Tezuka, N., Watanabe, M.M. Int. J. Syst. Evol. Microbiol. (2001) [Pubmed]
  14. Taxonomic revision of water-bloom-forming species of oscillatorioid cyanobacteria. Suda, S., Watanabe, M.M., Otsuka, S., Mahakahant, A., Yongmanitchai, W., Nopartnaraporn, N., Liu, Y., Day, J.G. Int. J. Syst. Evol. Microbiol. (2002) [Pubmed]
  15. A novel type of kleptoplastidy in Dinophysis (Dinophyceae): presence of haptophyte-type plastid in Dinophysis mitra. Koike, K., Sekiguchi, H., Kobiyama, A., Takishita, K., Kawachi, M., Koike, K., Ogata, T. Protist (2005) [Pubmed]
  16. Purification and characterization of recombinant affinity peptide-tagged oat phytochrome A. Murphy, J.T., Lagarias, J.C. Photochem. Photobiol. (1997) [Pubmed]
  17. Small Cab-like proteins regulating tetrapyrrole biosynthesis in the cyanobacterium Synechocystis sp. PCC 6803. Xu, H., Vavilin, D., Funk, C., Vermaas, W. Plant Mol. Biol. (2002) [Pubmed]
  18. Expression and characterization of cyanobacterium heme oxygenase, a key enzyme in the phycobilin synthesis. Properties of the heme complex of recombinant active enzyme. Migita, C.T., Zhang, X., Yoshida, T. Eur. J. Biochem. (2003) [Pubmed]
  19. Photochromic biliproteins from the cyanobacterium Anabaena sp. PCC 7120: lyase activities, chromophore exchange, and photochromism in phytochrome AphA. Zhao, K.H., Ran, Y., Li, M., Sun, Y.N., Zhou, M., Storf, M., Kupka, M., Böhm, S., Bubenzer, C., Scheer, H. Biochemistry (2004) [Pubmed]
  20. Characterization of Hemiselmis amylosa sp. nov. and phylogenetic placement of the blue-green cryptomonads H. amylosa and Falcomonas daucoides. Clay, B.L., Kugrens, P. Protist (1999) [Pubmed]
  21. Real time spectral analysis during phytochrome chromophore and chromoprotein purification. Zeidler, M., Lang, C., Hahn, J., Hughes, J. Int. J. Biol. Macromol. (2006) [Pubmed]
  22. Nonenzymatic chromophore attachment in biliproteins: conformational control by the detergent Triton X-100. Zhao, K.H., Zhu, J.P., Song, B., Zhou, M., Storf, M., Böhm, S., Bubenzer, C., Scheer, H. Biochim. Biophys. Acta (2004) [Pubmed]
  23. Chromophore attachment in phycocyanin. Functional amino acids of phycocyanobilin--alpha-phycocyanin lyase and evidence for chromophore binding. Zhao, K.H., Wu, D., Zhang, L., Zhou, M., Böhm, S., Bubenzer, C., Scheer, H. FEBS J. (2006) [Pubmed]
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