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Bilirubin Metabolism: An Overview

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Jaundice

Part of the book series: Hepatology ((H,volume 2))

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Abstract

Bilirubin is an open-chain tetrapyrrole with an approximate molecular weight of 585. The four pyrrole rings are linked by three carbon bridges of which two are unsaturated (outside) and one is saturated (central). The nature and order of the eight side chains located on the ß-carbons of the pyrrole rings are the same as in protoporphyrin IX. This finding led Fischer and his associates(1) to the conclusion that naturally-occurring bilirubin is derived from ferroprotoporphyrin IX (protoheme) by cleavage of the porphyrin ring at its α-methene carbon bridge; hence the resulting bilirubin is designated as IXα(l). Biliverdin IXα, a green-blue tetrapyrrole formed as an intermediate in the conversion of ferroprotoporphyrin IX to bilirubin IXα, possesses two hydrogen atoms less than bilirubin. It is probable that all bilirubin formed under biologic conditions has the IXα configuration(l), as cleavage of protoheme at carbon bridges other than the α-carbon bridge has not been demonstrated in vivo. The only known exception to this rule is the integumental pigment of a butterfly species (Pieris brassicae) which has been identified as biliverdin IXγ(2). It should be noted, however, that the naturally occurring bilirubin IXα can undergo isomeric scrambling about the central saturated carbon bridge, in that the molecule can split in the middle, permitting two left or two right dipyrryhnethenes to reassemble with themselves (3).

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Authors and Affiliations

  1. University of California, San Francisco, San Francisco, California, 94122, USA

    Rudi Schmid

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  1. Rudi Schmid
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Editors and Affiliations

  1. McGill University, Montreal, Quebec, Canada

    Carl A. Goresky M.D. (Professor of Medicine) (Professor of Medicine)

  2. University of Toronto, Toronto, Ontario, Canada

    Murray M. Fisher M.D. (Associate Professor of Medicine and Pathology) (Associate Professor of Medicine and Pathology)

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© 1975 Plenum Press, New York

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Schmid, R. (1975). Bilirubin Metabolism: An Overview. In: Goresky, C.A., Fisher, M.M. (eds) Jaundice. Hepatology, vol 2. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-2649-6_3

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  • DOI: https://doi.org/10.1007/978-1-4684-2649-6_3

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-2651-9

  • Online ISBN: 978-1-4684-2649-6

  • eBook Packages: Springer Book Archive

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