Collect. Czech. Chem. Commun.
2003, 68, 1007-1019
https://doi.org/10.1135/cccc20031007
On the Conformation of Glycobilirubin
Stefan E. Boiadjiev and David A. Lightner*
Chemistry Department, University of Nevada, Reno, Nevada 89557-0020 U.S.A.
Abstract
The first optically active glycine conjugate 1 of a bilirubin was prepared in several steps from (S)-β-methylxanthobilirubic acid glycine conjugate 8. The latter was synthesized by reaction of benzyl glycinate tosylate with the mixed anhydride formed in the reaction of (S)-β-methylxanthobilirubic acid 6 with isobutyl chloroformate. Spectroscopic analysis of the circular dichroism spectra of 1 in various solvents, including aqueous buffer, indicate a conformational preference for the M-helical ridge-tile conformation, thus providing the first spectroscopic evidence on the conformation of glycobilirubins.
Keywords: Glycine conjugate; Bilirubin; Hydrogen bonding; Pyrroles; CD spectroscopy; NMR; Porphyrins; Oligopyrroles; Amino acids; Conformation analysis.
References: 28 live references.
