Inactivation of plasma alpha 1-proteinase inhibitor by acrolein: adduct formation with lysine and histidine residues.

Molecular toxicology Pub Date : 1989-07-01
J C Gan, G A Ansari
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Abstract

Four new peaks were observed upon amino acid analysis of alpha 1-proteinase inhibitor (alpha 1-PI), which was inactivated by acrolein under in vitro conditions. The first peak emerged just before ammonia, the second and third between ammonia and lysine, and the fourth between histidine and arginine. The new fourth peak was also observed when model compounds of lysine (N-acetyllysine or polylysine) were reacted with acrolein and subsequently processed for amino acid analysis. This new compound was purified by high-voltage paper electrophoresis and subjected to fast atom bombardment mass spectrometry, which showed a protonated molecule ion at m/z 203 [M + H]+ followed by m/z 186 [M + H+ - NH3]+. This compound was thus identified as 3-oxopropyllysine, a lysine adduct of acrolein. Similarly, when a model polypeptide of histidine, polyhistidine, was reacted with acrolein under the same conditions as alpha 1-PI, three new peaks (besides histidine) emerged from the column. Their elution times corresponded to the first three new peaks found in the hydrolysates of acrolein treated alpha 1-PI.

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丙烯醛对血浆α 1蛋白酶抑制剂的失活作用:赖氨酸和组氨酸残基形成加合物。
体外丙烯醛灭活α 1-蛋白酶抑制剂(α 1-PI)后,氨基酸分析发现4个新峰。第一个峰出现在氨之前,第二个和第三个峰出现在氨和赖氨酸之间,第四个峰出现在组氨酸和精氨酸之间。当赖氨酸模型化合物(n -乙酰赖氨酸或聚赖氨酸)与丙烯醛反应并随后进行氨基酸分析时,也观察到新的第四个峰。该化合物经高压纸电泳和快速原子轰击质谱分析纯化后,在m/z 203 [m + H]+和m/z 186 [m + H+ - NH3]+处存在质子化的分子离子。该化合物因此被鉴定为3-氧丙基赖氨酸,丙烯醛的赖氨酸加合物。同样,当组氨酸的模型多肽polyhistidine与丙烯醛在与α 1-PI相同的条件下反应时,柱上出现了三个新的峰(除了组氨酸)。它们的洗脱时间与丙烯醛处理α - 1-PI的水解产物中发现的前三个新峰相对应。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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