A Novel Lipid Hydroperoxide-Derived Modification to Arginine
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- 作者：Tomoyuki Oe ; Seon Hwa Lee ; Maria V. Silva Elipe ; Byron H. Arison ; and Ian A. Blair
- 刊名：Chemical Research in Toxicology
- 出版年：2003
- 出版时间：December 2003
- 年：2003
- 卷：16
- 期：12
- 页码：1598 - 1605
- 全文大小：197K
- 年卷期：v.16,no.12(December 2003)
- ISSN：1520-5010
文摘
The guanidine group present in the amino acid arginine was found to react with the lipidhydroperoxide-derived bifunctional electrophile, 4-oxo-2-nonenal. The reaction between N
-tert-butoxycarbony-L-arginine and 4-oxo-2-nonenal resulted in the formation of an adduct(adduct A) that subsequently dehydrated on heating to adduct B. Liquid chromatography/mass spectrometry and nuclear magnetic resonance spectroscopy were used to assign thestructure of adduct B as (N
,N
'-etheno-2'-heptanon-2' '-one)-N-t-Boc-arginine. The reactionproceeded from initial reaction of the primary N-amino group at the C-1 aldehyde of 4-oxo-2-nonenal. Subsequently, an intramolecular Michael addition of a secondary N-amino groupoccurring at C-3 resulted in formation of the cyclic carbinolamine adduct A. Dehydration andrearrangement of the exocyclic imine resulted in the formation of adduct B, which containeda stable imidazole ring. The tetra peptide LRDE reacted with 4-oxo-2-nonenal primarily atarginine rather than at the amino terminus. This suggests that arginine-containing proteinscan react with lipid hydroperoxide-derived 4-oxo-2-nonenal to form a novel imidazole modification.
-tert-butoxycarbony-L-arginine and 4-oxo-2-nonenal resulted in the formation of an adduct(adduct A) that subsequently dehydrated on heating to adduct B. Liquid chromatography/mass spectrometry and nuclear magnetic resonance spectroscopy were used to assign thestructure of adduct B as (N,N'-etheno-2'-heptanon-2' '-one)-N-t-Boc-arginine. The reactionproceeded from initial reaction of the primary N-amino group at the C-1 aldehyde of 4-oxo-2-nonenal. Subsequently, an intramolecular Michael addition of a secondary N-amino groupoccurring at C-3 resulted in formation of the cyclic carbinolamine adduct A. Dehydration andrearrangement of the exocyclic imine resulted in the formation of adduct B, which containeda stable imidazole ring. The tetra peptide LRDE reacted with 4-oxo-2-nonenal primarily atarginine rather than at the amino terminus. This suggests that arginine-containing proteinscan react with lipid hydroperoxide-derived 4-oxo-2-nonenal to form a novel imidazole modification.