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A New Photoisomerization of Bilirubin
Lingjiang Cheng,
David A. Lightner,
Lingjiang Cheng
Department of Chemistry, University of Nevada, Reno, NV, USA
Search for more papers by this authorCorresponding Author
David A. Lightner
Department of Chemistry, University of Nevada, Reno, NV, USA
*Department of Chemistry, College of Arts and Sciences, Reno, NV 89557–0020, USA. Fax: 775–784–6804; e-mail:[email protected]Search for more papers by this authorLingjiang Cheng,
David A. Lightner,
Lingjiang Cheng
Department of Chemistry, University of Nevada, Reno, NV, USA
Search for more papers by this authorCorresponding Author
David A. Lightner
Department of Chemistry, University of Nevada, Reno, NV, USA
*Department of Chemistry, College of Arts and Sciences, Reno, NV 89557–0020, USA. Fax: 775–784–6804; e-mail:[email protected]Search for more papers by this authorAbstract
Photoirradiation of solutions of natural (4Z,15Z)-biliru-bin-IXα in chloroform with ˜366 nm UV light leads rapidly to a new photoisomer that has been characterized by NMR spectroscopy and by its (ground-state reaction) adducts with methanol and other protic nucleophiles. Unlike the previously described Z →E geometric isomeri-zation important in phototherapy of neonatal jaundice, the new photoisomerization involves regiospecific pho-toautomerization to afford 2-ethenyl-18-ethylidene-l,10,19,22,24-pentahydro-2,7,13,17-tetramethyl-l,19-dioxo-21H-biline-8,12-dipropanoic acid.
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