新型长效植物调节剂2-O-β-L-glucopyranoside-4-O-methyl phloracetophenone的全合成

Total Synthesis of a Novel Long-Effect Plant Growth Regulator: 2-O-β-L-Glucopyranoside-4-O-methyl Phloracetophenone

以β-L-(-)葡萄糖、无水醋酐及吡啶为原料,通过五步反应进行全合成,制备一种新型植物生长调节剂;β-D-葡萄糖水解酶催化下进行水解反应,研究其水解曲线。全合成产物经1H NMR鉴定为2-O-β-L-glucopyranoside-4-O-methyl phloracetophenone(1),总得率17.4%;水解实验表明domesticoside(2)可被β-D-葡萄糖水解酶水解为苷元,而化合物(1)不被水解。本法可作为一种新型长效生长调节剂的制备方法,也为体内快速被β-D-葡萄糖水解酶水解失活药物的结构修饰提供了新的思路。

In this study, a novel plant growth regulator was totally synthesized by using β-L- （-） glucose, anhydrous acetic anhydride and pyridine as raw materials＇ with five-steps of reaction. The hydrolization of the synthesized product catalyzed by β-D-glucosidase was carried out to investigate its hydrolytic curve. Results showed that the structure of the synthesized product was elucidated to be 2-O-β-L-glucopyranoside-4-O-methyl phloracetophenone （1） by NMR with a total yield of 17.4%. The hydrolization results showed that domesticoside （2） can be selectively hydrolyzed by β-D-glucusidase,bnt compound 1 cannot be hydrolyzed. Hence, it was concluded that the product synthesized in this study was a potential long-effect regulator. The reported synthetic routes can also be used as a novel idea to modify chemical drugs which might be rapidly inactivated by β-D-glucosidase.