Fluorophenyl Bilirubins: Synthesis and Stereochemistry |
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Authors: | Justin O. Brower David A. Lightner |
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Affiliation: | (1) Department of Chemistry, University of Nevada, Reno, NV 89557-0020, USA, US |
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Abstract: | Summary. Analogs of bilirubin with vinyl groups replaced by symmetrically-disposed o-fluorophenyls (1, bis-exo, and 2, bis-endo) were synthesized and characterized spectroscopically. Their 1H NMR spectra and NOE data are consistent with an intramolecularly hydrogen-bonded ridge-tile conformation where each propionic acid group embraces an opposing dipyrrinone. Like bilirubin, 1 and 2 exhibit negative chirality induced circular dichroism (ICD) Cotton effects in chloroform containing quinine. Unlike bilirubin, however, in aqueous buffer containing human serum albumin, 2 exhibits a negative exciton chirality ICD, whereas that of 1 is positive. Received May 22, 2001. Accepted May 29, 2001 |
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Keywords: | . Pyrroles Conformation Hydrogen-bonding Circular dichroism. |
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