- Synthesis of biliverdins with stable extended conformations. Part I
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Biliverdins with extended conformations stabilized by intramolecular ethyl bridges were obtained by base treatment of helical biliverdins with 2-chloroethyl side chains. Thus, neobiliverdin IXβ (6) was obtained by reaction of 13,18-di-(2-chloroethyl)-bili
- Iturraspe, Jose,Bari, Sara E.,Frydman, Benjamin
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- Photochemistry of Biliverdin IXδ as a Model for the Study of the Photoproducts from Natural Biliverdin IXγ (Pterobilin)
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The configurations of biliverdin-IXγ and -IXδ 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 is also formed in degassed solution (Φ = 4E-5) but pigments 4, 5 and 6 arise from photo-oxidation with O2.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).
- Bois-Choussy, Michele,Barbier, Michel
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p. 1098 - 1110
(2007/10/02)
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