O-酰基化丝氨酸的合成及其对樱桃番茄乙烯合成量和果实硬度的影响

通过L-丝氨酸与不同的酰氯在室温下反应，合成了8个未见文献报道的乙烯合成抑制剂O-酰基化丝氨酸（2a~2h），其结构通过核磁共振氢谱、碳谱及高分辨质谱确证。以氨乙氧乙烯基甘氨酸（aminoethoxyvinylglycine，AVG）为阳性对照，测定了目标化合物对樱桃番茄Lycopersivon esculentum Mill.乙烯合成量和果实硬度的影响，同时运用分子对接的方法分析了目标化合物与番茄1-氨基环丙烷羧酸（1-aminocyclopropane-1-carboxylic acid， ACC）合成酶（ACS， 1IAY）可能的结合模式。结果显示:大部分目标化合物具有延缓樱桃番茄果实软化和抑制乙烯合成的作用，其中化合物2c和2h效果较为突出。用2c和2h处理番茄后第5天，与空白对照相比，果实硬度分别提高27.62%和40.04%，均与AVG处理无显著性差异；2c和2h对乙烯合成量的抑制率分别达71.89%和53.28%，其中2c处理的抑制效果显著优于AVG处理。分子对接方法分析结果表明:化合物2c与番茄ACS酶活性空腔的氨基酸残基有较好的相互作用，2c的羧基可与Ala54和Arg412的氨基形成氢键，从而占据ACS酶的活性空腔。O-酰基化丝氨酸类化合物结构简单，容易获取，对乙烯合成抑制剂的开发具有推动作用。

Synthesis of O-acylatedserine and its effect on ethylene synthesis and fruit firmness of cherry tomato

The eight novel inhibitors of ethylene biosynthesis were synthesized from L-serine reactions with acyl chlorides at room temperature, and their structures were confirmed by ¹H and ¹³C NMR and HRMS. Fruit firmness and ethylene production were measured after cherry tomato (Lycopersivon esculentum Mill.) were treated with O-acylatedserines and aminoethoxyvinylglycine (AVG). Furthermore, the probable binding mode of (1-aminocyclopropane-1-carboxylic acid, ACC) synthase(ACS enzyme,1IAY) and target compound was analyzed using Molecular Docking method. The results showed most of the target compounds is able to delay cherry tomato fruit softening and inhibit ethylene biosynthesis. The effects of compounds 2c and 2h were more prominent, and the fruit firmness was increased by 27.62% and 40.04%, respectively, compared with the blank control on the 5^th day after the treatment, and there was no significant difference with AVG treatment. 2c and 2h inhibited the synthesis of ethylene by 71.89% and 53.28% compared with the blank control, respectively. And the inhibition effect of 2c treatment was significantly higher than that of AVG. Analysis result of Molecular Docking method indicated that 2c showed strong interactions with tomatos ACC, and the carboxyl group of 2c could form hydrogen bonds with the amino groups of Ala54 and Arg412, thus occupying the active cavity of ACS enzyme. This type of compound has a simple structure and is easy to obtain and contributes to the development of ethylene synthesis inhibitors.