Premium
Phytochrome Models, I. Isolation, Characterization, and Solution Conformation of Biliverdin Dimethyl Ester and Its XIIIα Isomer
Author(s) -
Lehner Harold,
Braslavsky Silvia E.,
Schaffner Kurt
Publication year - 1978
Publication title -
justus liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0075-4617
DOI - 10.1002/jlac.197819781214
Subject(s) - biliverdin , chemistry , circular dichroism , bile pigments , stereochemistry , biliverdin reductase , nuclear overhauser effect , nuclear magnetic resonance spectroscopy , organic chemistry , heme , enzyme , pigment , heme oxygenase
Biliverdin dimethyl ester ( 1b; IXα) and its XIIIα isomer 2b have been isolated on a preparative scale after esterification of an isomeric mixture obtained by oxidation of bilirubin. Both isomers readily form solid solutions. The substitution patterns and the predominant helical „ all‐Z” configuration, „ all‐syn” conformation of 1b and 2b are assigned on the basis of an 1 H‐NMR study including spin decoupling and nuclear Overhauser effect experiments. The electronic absorption spectra of the two isomers differ significantly. The ethyl ( S )‐(‐)‐lactate‐induced circular dichroism of 1b and 2b in the long and short wavelength regions is similar to that found for biliverdin‐peptide complexes.