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Sulfotransferase-Mediated Activation of Some Benzylic and Allylic Alcohols

  • Young-Joon Surh
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 387)

Abstract

Sulfo-conjugation in general renders the lipophilic xenobiotics water-soluble, thereby facilitating their removal from the body through excretion in urine or bile. Under certain circumstances, however, sulfonation can also contribute to toxification of some classes of chemicals (recently reviewed by Miller, 1994; Miller and Surh, 1994). Since the first discovery of 2-acetylaminofluorene-N-sulfate as an electrophilic metabolite of N-hydroxy-2-acetylaminofluorene (Debaun et al., 1968; King and Phillips, 1968), there has been accumulated evidence for the association between sulfonation and induction of tumors by this carcinogen and others. Although the “bay-region” theory is widely accepted as a general concept in determining the tumorigenicity of polycyclic aromatic compounds (PAH) in general, recent studies have shown that PAHs bearing benzylic hydroxyl functional groups can also be activated via sulfuric acid esterification (vide infra). This report briefly reviews our recent findings on metabolic activation of some benzylic alcohols to electrophilic, mutagenic, or carcinogenic sulfate esters. The paper also concerns the sulfate ester of the heterocyclic allylic alcohol, 5-hydroxymethylfurfural, as a novel example of electrophilic species formed by sulfotransferase activity.

Keywords

Benzylic Alcohol Sulfate Ester Maillard Reaction Product Bacterial Mutagenicity Allylic Alcohol 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer Science+Business Media New York 1996

Authors and Affiliations

  • Young-Joon Surh
    • 1
  1. 1.Division of Environmental Health Sciences Department of Epidemiology and Public HealthYale University School of MedicineNew HavenUSA

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