摘要
L-氮杂环丁烷-2-羧酸(L-Aze)是广泛存在于植物中的非蛋白源氨基酸,其独特的氮杂四元环状结构使得该类化合物表现出了显著的化学反应活性和多维的生理活性。目前,LAze的制备仍以化学合成为核心路径,其合成策略呈现出多样性,近期报道的合成路线可实现其kg级制备,具有工业化潜力。L-Aze具有手性氮杂四元环张力结构,不仅是制备手性氮杂环丁烷类天然产物及活性药物分子的重要合成砌块,还可用作手性催化剂和药效团。生物活性研究表明,L-Aze能竞争性模拟脯氨酸参与蛋白质合成,干扰蛋白质正常的新陈代谢,对部分植物、细菌、病毒、真菌和蓝藻有抑制作用,而且在多个动物模型中也表现出了生长抑制作用。特别值得关注的是,L-Aze对瓜类白粉病呈现显著治疗效果,同时对蓝藻展现出强效抑制作用,这些特性使其在新型植物源农用杀菌剂开发领域具有重要潜力。此外,L-Aze的刚性环状骨架作为优势结构单元,已被广泛应用于酶抑制剂、抗疟疾药物以及镇痛药剂的结构修饰与功能优化。本文重点综述了L-Aze的化学合成及其在杀菌活性方面的研究进展,可为其作为新型绿色农药的开发提供科学参考。
L-Azetidine-2-carboxylic acid(L-Aze)is a non-proteinogenic amino acid present in certain plant species.Characterized by unique azetidine structure(nitrogen-containing four-membered ring),this compound exhibits remarkable chemical reactivity and diverse physiological activities.Currently,the synthesis of L-Aze is mainly confined to chemical approaches,with diverse synthetic strategies having been reported.Notably,newly developed synthetic routes have achieved kilogram-scale production,indicating significant industrial production potential.Due to its a strained chiral azetidine ring system,L-Aze serves not only as a crucial building block for synthesizing chiral azetidinecontaining natural products and bioactive pharmaceutical molecules,but also it has applications in chiral catalysis and pharmacophore design.Biological activity studies reveal that L-Aze can competitively mimic proline during protein synthesis,thereby disrupting normal protein metabolism.It exhibits broad inhibitory effects across diverse organisms,including plants,bacteria,viruses,fungi,and cyanobacteria,and also inhibits growth in multiple animal models.Notably,it demonstrates remarkable efficacy against cucurbit powdery mildew and potent inhibition of cyanobacteria,positioning it as a promising candidate for developing novel plant-derived fungicide.Furthermore,its rigid cyclic framework,an advantageous structural unit,has been extensively utilized in the structural modification and functional optimization of enzyme inhibitors,antimalarial drugs,and analgesics.This review summarizes the chemical synthesis and fungicidal activity of L-Aze,which can provide scientific basis for its development as a novel green pesticide.
作者
禹克银
张继文
吴文君
YU Keyin;ZHANG Jiwen;WU Wenjun(College of Chemistry&Pharmacy,Northwest A&F University,Yangling 712100,Shaanxi Province,China;College of Plant Protection,Northwest A&F University,Key Laboratory of Botanical Pesticide R&D in Shaanxi Province,Yangling 712100,Shaanxi Province,China)
出处
《农药学学报》
北大核心
2026年第1期13-32,共20页
Chinese Journal of Pesticide Science
基金
中国博士后科学基金(No.2024M752643)
西北农林科技大学科研启动费(No.2452022147)。
