Xu Hui, Ye Jia, Lin Longyuan, Lian Minmin, Chen Jicheng
College of Food Science, Fujian Agriculture and Forestry University, Fuzhou 350002, China.
J Agric Food Chem. 2024 May 29;72(21):12251-12259. doi: 10.1021/acs.jafc.4c02576. Epub 2024 May 14.
A novel technique for generating tetramethylpyrazine (TTMP) was proposed, carried out on a phenolics-Fenton coupled redox cycling system in an acetoin-ammonium acetate (AA-ACT) pattern reaction. The TTMP generation employing the Fenton system is a first-order reaction that significantly increased the reaction rate, especially in the early stages, distinguishing it from the original zero-order kinetics reaction pattern. Further, the Fenton reaction effectively promotes the TTMP generation at lower temperature, and epigallocatechin gallate (EGCG) could reset the Fenton reaction, accomplishing the redox cycle. We have discovered a novel class of intermediate products, N-substituted amides, which act as a reservoir and transform into amino acid, then undergo aromatization to generate TTMP. The results provide a useful supplement for intelligent synthesis route design, and a new approach for understanding the transformation pathways of pyrazines.
提出了一种生成四甲基吡嗪（TTMP）的新技术，该技术在乙偶姻-醋酸铵（AA-ACT）模式反应的酚类-芬顿耦合氧化还原循环系统上进行。采用芬顿系统生成TTMP是一级反应，显著提高了反应速率，尤其是在早期阶段，这使其有别于原始的零级动力学反应模式。此外，芬顿反应在较低温度下有效地促进了TTMP的生成，而表没食子儿茶素没食子酸酯（EGCG）可以重置芬顿反应，完成氧化还原循环。我们发现了一类新型的中间产物，即N-取代酰胺，它们作为储存库，转化为氨基酸，然后进行芳构化生成TTMP。这些结果为智能合成路线设计提供了有益的补充，并为理解吡嗪的转化途径提供了新方法。
