Pterobilin

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Pterobilin
Identifiers
3D model (
JSmol
)
ChemSpider
UNII
  • InChI=1S/C23H21N3O2S2/c1-15-3-5-19(16(2)11-15)20-14-30-23(26-20)29-13-18-4-6-21(28-18)22(27)25-12-17-7-9-24-10-8-17/h3-11,14H,12-13H2,1-2H3,(H,25,27)
    Key: QWUAUCVIVCXEEL-UHFFFAOYSA-N
  • CC1=C(CCC(=O)O)\C(=C\c2[nH]c(\C=C/3\N=C(\C=C\4/NC(=O)C(=C4C)CCC(=O)O)C(=C3C)C=C)c(C=C)c2C)\NC1=O
Properties
C33H34N4O6
Molar mass 582.6536
Density 1.3±0.1 g/cm3[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Graphium sarpedon which contains pterobilin

Pterobilin also called biliverdin IXγ in the Fischer nomenclature,

P. weiskei), and sarpedobilin, which is used by Graphium sarpedon.[4]

Synthetic pathways

Pterobilin is a

δ-aminolevulinic acid, then coproporphyrinogen III, to protoporphyrin IX and finally into pterobilin.[5][6]

Pterobilin can be

phototransformed into phorcabilin and sarpedobilin in vitro.[5] Pterobilin can also be thermally rearranged in vitro into phorcabilin.[5][7]

Biochemical roles

Pterobilin in P. brassicae

wing scales where pterobilin accumulates differ morphologically in a way that would facilitate photoreception.[5]

See also


References

  1. ^ "Pterobilin (Found by synonym)". ChemSpider. Retrieved 21 January 2020.
  2. PMID 3208761
    .
  3. OCLC 5510989
    . Retrieved 8 February 2018.
  4. ^
    ISBN 978-953-51-0431-5
    . Retrieved 8 February 2018.
  5. ^
    PMID 6838551
    .
  6. ^ Rüdiger, W., Klose, W., Vuillaume, M., and Barbier, M. (1969). Experimentia, 25, 487-488.
  7. ^ Bois-Choussy, Michèle; Barbier, Michel (1978). Heterocycles 9, 677-690.
  8. ^ Barbier, Michel, Bergerard, J., Hurpin, B., and Vuillaume, M. (1970). Comptes rendus de l'Académie des Sciences Paris, 271, 342-345.
  9. ^ Vuillaume, M., and Bergerard, J. (1978). Chronobiologia, 5, 286-292.
  10. ^ Vuillaume, M., and Dattée, Y. (1980). Archives de zoologie expérimentale et générale, 121, 159-164.
  11. ^ Allyn, A. C., Barbier, Michel, Bois-Choussy, Michèle, and Rothschild, M. (1981). Antenna, Londres, 29-31.
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