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首页> 外文期刊>Journal of mass spectrometry: JMS >Novel glutathione conjugates of phenyl isocyanate identified by ultra-performance liquid chromatography/electrospray ionization mass spectrometry and nuclear magnetic resonance
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Novel glutathione conjugates of phenyl isocyanate identified by ultra-performance liquid chromatography/electrospray ionization mass spectrometry and nuclear magnetic resonance

机译：超高效液相色谱/电喷雾电离质谱和核磁共振法鉴定新型异氰酸苯酯的谷胱甘肽共轭物

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摘要

Phenyl isocyanate is a highly reactive compound that is used as a reagent in organic synthesis and in the production of polyurethanes. The potential for extensive occupational exposure to this compoundmakes it important to elucidate its reactivity towards different nucleophiles and potential targets in the body. In vitro reactions between glutathione and phenyl isocyanate were studied. Three adducts of glutathione with phenyl isocyanate were identified using ultra-performance liquid chromatography/ electrospray ionization mass spectrometry and nuclear magnetic resonance (NMR). Mass spectrometric data for these adducts have not previously been reported. Nucleophilic attack on phenyl isocyanate occurred via either the cysteinyl thiol group or the glutamic acid α-amino group of glutathione. In addition, a double adduct was formed by the reaction of both these moieties. NMR analysis confirmed the proposed structure of the double adduct, which has not previously been described. These results suggest that phenyl isocyanate may react with free cysteines, the α-amino group and also with lysine residues whose side chain contains a primary amine.
机译：异氰酸苯基酯是一种高度反应性的化合物，在有机合成和聚氨酯生产中用作试剂。大量职业接触该化合物的潜力使其变得重要，阐明其对体内不同亲核试剂和潜在靶标的反应性。谷胱甘肽和异氰酸苯酯之间的体外反应进行了研究。使用超高效液相色谱/电喷雾电离质谱和核磁共振（NMR）鉴定了谷胱甘肽与异氰酸苯酯的三种加合物。这些加合物的质谱数据先前尚未报道。异氰酸苯酯的亲核攻击是通过谷胱甘肽的半胱氨酸硫醇基或谷氨酸α-氨基发生的。另外，通过这两个部分的反应形成双加合物。 NMR分析证实了所提出的双加合物的结构，该结构以前没有描述过。这些结果表明异氰酸苯酯可以与游离的半胱氨酸，α-氨基以及其侧链包含伯胺的赖氨酸残基反应。

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