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.
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Received May 22, 2001. Accepted May 29, 2001
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Brower, J., Lightner, D. Fluorophenyl Bilirubins: Synthesis and Stereochemistry. Monatshefte für Chemie 132, 1527–1546 (2001). https://doi.org/10.1007/s007060170010
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DOI: https://doi.org/10.1007/s007060170010