作者:Silvio Uhlig、Lada Ivanova、Christopher O. Miles
DOI:10.1021/acs.chemrestox.9b00385
日期:2020.2.17
species of Fusarium, which may infect grain crops. DON, as well as other type-B trichothecenes, contain an α,β-unsaturated carbonyl group that may react with sulfhydryl groups in, for example, amino acids and peptides. Such conjugates have been shown to occur in plants. Nucleophilic addition of thiols to the conjugated double bond in DON afforded several isomeric reaction products, and the thermodynamically
脱氧雪腐烯酚(DON)是一种三态镰刀菌霉菌毒素,由几种镰刀菌产生,可能会感染粮食作物。DON,以及其他B型三色烯,都包含一个α,β-不饱和羰基,可以与例如氨基酸和肽中的巯基反应。此类缀合物已显示出存在于植物中。硫醇向DON中共轭双键的亲核加成反应提供了几种异构体反应产物,并且DON-10半胱氨酸和DON-10-谷胱甘肽的热力学上有利的异构体已经被制备和表征。这项研究报告了动力学上受人欢迎的DON-10-半胱氨酸异构体的制备和表征。我们随后研究并比较了两种DON-10-半胱氨酸异构体的解偶联反应速率和热力学上有利的DON-10-谷胱甘肽加合物。即使在pH 10.7时,热力学上有利的硫醇偶联物的解偶联速率也很慢,半衰期为数周,而动力学上有利的DON-10半胱氨酸异构体在数小时内解偶联,得到游离的DON。我们采用了一种简单而快速的氧化方案,在该方案中,硫化物键被氧化为亚砜或砜,当用碱处理时,迅速