Aspongopyrimidine A, a N-Peralkylated Histidine Zwitterion from Aspongopus chinensis against Alzheimer’s Disease Targeting MAPRE3,Organic Letters

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Aspongopyrimidine A, a N-Peralkylated Histidine Zwitterion from Aspongopus chinensis against Alzheimer’s Disease Targeting MAPRE3
Organic Letters ( IF 4.9 ) Pub Date : 2024-02-12 , DOI: 10.1021/acs.orglett.4c00214
Yong-Ming Yan ₁ , Ji-Jun Li ₁ , Yong-Xian Cheng ₁

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Aspongopyrimidine A (1), a hexa-1,3-diene-histidine-hexanoic acid adduct featuring a 4,5-dihydro-2H-10λ⁴-imidazo[5,1-f]pyrrolo[2,1-b]pyrimidine motif, was isolated from the insect Aspongopus chinensis. The structure was clarified by spectroscopic and computational methods and X-ray diffraction. Peralkylation of N-atoms in histidine by two C6 units makes 1 an inner salt with a 5/6/5 tricyclic system. Biological evaluation found that 1 exerts activity against Alzheimer’s disease targeting MAPRE3 through a chemical proteomics approach. This study revealed unusual modifications of amino acids as the fundamental units of protein.

中文翻译：

Aspongopyrimidine A，一种来自 Aspongopus chinensis 的 N-全烷基化组氨酸两性离子，针对 MAPRE3 对抗阿尔茨海默病

Aspongopyrimidine A ( 1 )，一种六-1,3-二烯-组氨酸-己酸加合物，具有 4,5-二氢-2 H -10λ ^{4 -}咪唑并[5,1- f ]吡咯并[2,1- b ]嘧啶基序，是从昆虫Aspongopus chinensis中分离出来的。通过光谱和计算方法以及X射线衍射阐明了结构。组氨酸中的N原子被两个 C6 单元全烷基化，使1成为具有 5/6/5 三环系统的内盐。生物学评估发现， 1通过化学蛋白质组学方法针对 MAPRE3 发挥抗阿尔茨海默氏病的活性。这项研究揭示了作为蛋白质基本单位的氨基酸的不寻常修饰。

更新日期：2024-02-12

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