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A New Photoisomerization of Bilirubin
Author(s) -
Cheng Lingjiang,
Lightner David A.
Publication year - 1999
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1999.tb08306.x
Subject(s) - photoisomerization , isomerization , chemistry , chloroform , photochemistry , methanol , adduct , nucleophile , spectroscopy , medicinal chemistry , organic chemistry , catalysis , physics , quantum mechanics
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.