These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


Pubmed for Handhelds

PUBMED FOR HANDHELDS

Search MEDLINE/PubMed

  • Title: 2-Alkylpyrrole formation from 4,5-epoxy-2-alkenals.
    Author: Zamora R, Hidalgo FJ.
    Journal: Chem Res Toxicol; 2005 Feb; 18(2):342-8. PubMed ID: 15720141.
    Abstract:
    N-Substituted 2-pentylpyrrole formation has been related to the etiology or the consequences of several diseases in which lipid oxidation is involved. This study describes the formation of N-substituted 2-alkylpyrroles in the reaction of 4,5-epoxy-2-alkenals with amino compounds and suggests an alternative pathway for the formation of these compounds that are nowadays commonly accepted to be produced by reaction of the lipid oxidation product 4-hydroxy-2-nonenal with primary amino compounds. The described reaction constitutes a new route for pyrrole production in the lipid peroxidation pathway when it takes place in the presence of amino compounds and implies the loss of one carbon in the 4,5-epoxy-2-alkenal during the formation of the heterocyclic ring, which is proposed to be released as formaldehyde. This reaction also confirms the high reactivity of 4,5-epoxy-2-alkenals, which are usually found in smaller amounts than other lipid oxidation products. Their importance in vivo may be underappreciated in part as a consequence of this high reactivity that brings about their rapid disappearance.
    [Abstract] [Full Text] [Related] [New Search]