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Syntheses of Bile Pigments. Part 18 . Synthesis and conformational studies of oxa‐ and thia‐deaza‐biliverdin analogues
Author(s) -
Nesvadba Petr,
NgocPhan Do,
Nydegger Fredy,
Ferao Arturo Espinosa,
Gossauer Albert
Publication year - 1994
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.19940770715
Subject(s) - chemistry , biliverdin , bile pigments , pigment , stereochemistry , biochemistry , heme , organic chemistry , enzyme , heme oxygenase
Following the conventional methodology used for the synthesis of bile pigments, some oxa‐ and thia‐deazabiliverdin analogues were synthetized for the first time. Both UV/VIS spectroscopic and 1 H{ 1 H}‐NOE difference studies reveal that the oxa‐deaza‐biliverdin analogue 8a occurs in apolar solvents in a partly ‘stretched’ conformation, whereas the corresponding thia derivative 8b behaves rather like a genuine bile pigment. Unexpectedly, the helical‐shaped conformation is also preponderant in a trioxa‐trideaza‐biliverdin analogue, which could be only characterized in its protonated form 14 .