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Photochemistry of Biliverdin IX δ as a model for the study of the photoproducts from natural biliverdin IX γ (pterobilin)
Author(s) -
BoisChoussy Michèle,
Barbier Michel
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630437
Subject(s) - biliverdin , chemistry , isomerization , bile pigments , photochemistry , pigment , organic chemistry , heme , catalysis , heme oxygenase , enzyme
The configurations of biliverdin‐IX γ and ‐IX δ dimethyl esters 1 and 2 in solutions, have been studied using Nuclear‐ Overhauser ‐Effect (NOE) experiments. Irradiation (500‐700 nm) of biliverdin IXδ gave syn‐Z → anti‐E isomerization of the central methine bridge and in aerated polar solutions, four new cyclized pigments were isolated for which structures 3, 4, 5 and 6 are proposed. Neobiliverdin IXδ 3 is also formed in degassed solution (Φ=4.10 −5 ) but pigments 4, 5 and 6 arise from photo‐oxidation with O 2 . Biliverdin IXδ appears to be a good model for the study of photo‐reactions occurring on the vinyl groups of the natural biliverdin IXγ (pterobilin).