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 5th 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.