Synthesis of the lipid peroxidation product 4-hydroxy-2(E)-nonenal with 13C stable isotope incorporation

✍ Scribed by I. Jouanin; V. Sreevani; E. Rathahao; F. Guéraud; A. Paris

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: French
• Weight: 200 KB
• Volume: 51
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.1485

✦ Synopsis

Abstract

The aim of this work was to synthesize ^13^C internal standards for the quantification of 4‐hydroxy‐2(E)‐nonenal (HNE), a lipid peroxidation product, and of the etheno‐adducts possibly formed by HNE damage to DNA nucleobases. We designed an eight‐step synthesis starting from ethyl 2‐bromoacetate and giving access to 4‐[(tetrahydro‐2H‐pyran‐2‐yl)oxy]‐2(E)‐nonenal. This compound is a precursor of HNE. The scheme was then used to produce the ^13^C precursor [1,2‐^13^C~2~]‐4‐[(tetrahydro‐2H‐pyran‐2‐yl)oxy]‐2(E)‐nonenal. [1,2‐^13^C~2~]‐HNE was obtained by acid deprotection. All the intermediary and final compounds were fully characterized by IR, HRMS, ^1^H and ^13^C NMR. It is the first synthesis of HNE which enables the incorporation of two ^13^C labels at determined positions. Copyright © 2008 John Wiley & Sons, Ltd.