Tsai L, Sokoloski E A
Laboratory of Biochemistry, National Heart, Lung, and Blood Institute, National Institutes of Health, Bethesda, MD, USA.
Free Radic Biol Med. 1995 Jul;19(1):39-44. doi: 10.1016/0891-5849(95)00009-m.
The reaction of 4-hydroxy-2-nonenal and N alpha-acetyl-L-histidine was studied in pH 7.1 phosphate buffer. The main product isolated was assigned a cyclic hemiacetal structure formed by the addition of one of the imidazole nitrogen atoms to the alpha,beta-unsaturated aldehyde system of 4-hydroxy-2-nonenal. This structural assignment was based on the analyses of the NMR and mass spectral data of two derivatives obtained from the cyclic hemiacetal. The establishment of this cyclic hemiacetal structure supports the proposal made by Uchida and Stadtman6 that 4-hydroxy-2-nonenal modified histidyl residues in insulin by a Michael reaction.
在pH 7.1的磷酸盐缓冲液中研究了4-羟基-2-壬烯醛与Nα-乙酰基-L-组氨酸的反应。分离得到的主要产物被确定为一种环状半缩醛结构，它是由咪唑氮原子之一加成到4-羟基-2-壬烯醛的α,β-不饱和醛体系上形成的。这一结构归属是基于对从环状半缩醛得到的两种衍生物的核磁共振和质谱数据的分析。这种环状半缩醛结构的确定支持了内田和斯塔特曼提出的观点，即4-羟基-2-壬烯醛通过迈克尔反应修饰胰岛素中的组氨酰残基。
