Conformational analysis and circular dichroism of bilirubin, the yellow pigment of jaundice

David A. Lightner; Richard Person; Blake Peterson; Gisbert Puzicha; Yu-Ming Pu; Stefan Bojadziev

doi:10.1117/12.44204

1 June 1991 Conformational analysis and circular dichroism of bilirubin, the yellow pigment of jaundice

David A. Lightner, Richard Person, Blake Peterson, Gisbert Puzicha, Yu-Ming Pu, Stefan Bojadziev

Proceedings Volume 1432, Biomolecular Spectroscopy II; (1991) https://doi.org/10.1117/12.44204
Event: Optics, Electro-Optics, and Laser Applications in Science and Engineering, 1991, Los Angeles, CA, United States

Abstract

Conformational analysis of (4Z, 15Z)-bilirubin-IX(alpha) by molecular mechanics computations reveals a global energy minimum folded conformation. Powerful added stabilization is achieved through intramolecular hydrogen bonding. Theoretical treatment of bilirubin as a molecular exciton predicts an intense bisignate circular dichroism spectrum for the folded conformation: (Delta) (epsilon) is congruent to 270 L (DOT) mole-1 (DOT) cm-1 for the $OM450 nm electronic transition(s). Synthesis of bilirubin analogs with propionic acid groups methylated at the (alpha) or (beta) position introduces an allosteric effect that allows for an optical resolution of the pigments, with enantiomers exhibiting the theoretically predicted circular dichroism.

Citation Download Citation

David A. Lightner, Richard Person, Blake Peterson, Gisbert Puzicha, Yu-Ming Pu, and Stefan Bojadziev "Conformational analysis and circular dichroism of bilirubin, the yellow pigment of jaundice", Proc. SPIE 1432, Biomolecular Spectroscopy II, (1 June 1991); https://doi.org/10.1117/12.44204

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