The Journal of Organic Chemistry

Independent synthesis, solution behavior, and studies on the mechanism of formation of a primary amine-derived fluorophore representing cross-linking of proteins by …

G Xu, Y Liu, LM Sayre

Index: Xu, Guozhang; Liu, Yahua; Sayre, Lawrence M. Journal of Organic Chemistry, 1999 , vol. 64, # 16 p. 5732 - 5745

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Citation Number: 69

Abstract

Lipid peroxidation in aging and degenerative disease results in the production of 4-hydroxy- 2-alkenals that modify proteins and give rise to both protein cross-linking and fluorophore generation. Recent model studies demonstrated that the major ex/em 360/430 fluorophore formed from (E)-4-hydroxy-2-nonenal (HNE) or (E)-4-hydroxy-2-hexenal (HHE) and protein lysine-based amine is a 2-alkyl-2-hydroxy-1, 2-dihydropyrrol-3-one iminium 1: 2 cross-link ...

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