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Review ArticleMinireview

Unusual Glucuronides

Upendra A. Argikar
Drug Metabolism and Disposition July 2012, 40 (7) 1239-1251; DOI: https://doi.org/10.1124/dmd.112.045096
Upendra A. Argikar
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Abstract

Glucuronidation reaction is catalyzed by mammalian uridine diphosphoglucuronosyl transferases by using uridine diphosphoglucuronic acid as a cosubstrate. Conjugation of glucuronic acid to nucleophilic functional groups in chemical entities results in formation of glucuronides. As anticipated, a number of nucleophilic functional groups such as hydroxyl, phenolic, acyl, primary secondary and tertiary amino, etc. in a diverse set of chemical compounds are known to form the corresponding glucuronides. Glucuronides have been reported to be formed at carbon atoms, selenium atoms, and upon N-carbamoylation of primary and secondary amino groups. Glucuronides are also believed to be the end products of metabolism. However, there are examples where glucuronidation results in further oxidative or conjugative biotransformation reactions. The objective of this review is to highlight unusual glucuronide conjugates. Diglucuronide conjugates reported in the literature fall under two distinct categories. Use of prefixes such as “bis” versus “di” has been previously proposed for separating the two types of diglucuronides. In spite of this, literature reports for diconjugative glucuronide metabolites reflect interchangeable use of “bisglucuronides” and “diglucuronides.” Furthermore, the application of such prefixes does not adhere to recommendations of International Union of Pure and Applied Chemistry nomenclature for substituent groups. Therefore, an effort is made in this review to document the historic reports for diglucuronides into two distinct types for sake of clarity and to allow differentiation between the two types of diconjugative metabolites. Overall, this commentary centers on unusual glucuronide metabolites that result from conjugation at uncommon functional groups, glucuronides undergoing ensuing oxidative or conjugative metabolic transformations. Structural and mechanistic aspects are also discussed.

Footnotes

  • Article, publication date, and citation information can be found at http://dmd.aspetjournals.org.

    http://dx.doi.org/10.1124/dmd.112.045096.

  • ABBREVIATIONS:

    UDP-GlcUA
    uridine diphosphoglucuronic acid
    UGT
    uridine diphosphoglucuronosyl transferase
    Se
    seleno
    DPPIV
    dipeptidyl peptidase IV.

  • Received February 16, 2012.
  • Accepted April 19, 2012.
  • Copyright © 2012 by The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 40 (7)
Drug Metabolism and Disposition
Vol. 40, Issue 7
1 Jul 2012
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Review ArticleMinireview

UNUSUAL GLUCURONIDES

Upendra A. Argikar
Drug Metabolism and Disposition July 1, 2012, 40 (7) 1239-1251; DOI: https://doi.org/10.1124/dmd.112.045096

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Review ArticleMinireview

UNUSUAL GLUCURONIDES

Upendra A. Argikar
Drug Metabolism and Disposition July 1, 2012, 40 (7) 1239-1251; DOI: https://doi.org/10.1124/dmd.112.045096
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  • Article
    • Abstract
    • Introduction
    • Usual Glucuronides
    • Carbon-Linked Glucuronides
    • Sulfur-Linked Glucuronides
    • Selenium-Linked Glucuronides
    • Carbamoyl Glucuronides
    • Diglucuronide Conjugates
    • Glucuronide-Sulfate Diconjugates
    • Glucuronides Undergoing Subsequent Oxidative Metabolism
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