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Proceedings Paper

Conformational analysis and circular dichroism of bilirubin, the yellow pigment of jaundice
Author(s): David A. Lightner; Richard Person; Blake Peterson; Gisbert Puzicha; Yu-Ming Pu; Stefan Bojadziev
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Paper 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.

Paper Details

Date Published: 1 June 1991
PDF: 12 pages
Proc. SPIE 1432, Biomolecular Spectroscopy II, (1 June 1991); doi: 10.1117/12.44204
Show Author Affiliations
David A. Lightner, Univ. of Nevada/Reno (United States)
Richard Person, Univ. of Nevada/Reno (United States)
Blake Peterson, Univ. of Nevada/Reno (United States)
Gisbert Puzicha, Univ. of Nevada/Reno (United States)
Yu-Ming Pu, Univ. of Nevada/Reno (United States)
Stefan Bojadziev, Univ. of Nevada/Reno (United States)

Published in SPIE Proceedings Vol. 1432:
Biomolecular Spectroscopy II
Robert R. Birge; Laurence A. Nafie, Editor(s)

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