半乳糖苷脂肪酸酯的选择性合成及其对Staphylococcus aureus和Salmonella agona的抗菌性

以甲基β-D-半乳糖苷为底物,用二丁基二甲氧锡作锡络合剂,脂肪酸酰氯作酰化剂选择性地合成半乳糖苷脂肪酸酯。最佳反应条件为:n(甲基β-D-半乳糖苷)∶n(二丁基二甲氧锡)∶n(脂肪酸酰氯)=1∶1.1∶1.1,温度为25℃,甲基3-O-脂肪酸酰基-β-D-半乳糖苷收率可达70%左右。并应用该糖酯类化合物作细菌Staphylococcusaureus和Salmonella agona的抗菌性测试,结果表明月桂酸酯和豆蔻酸酯分别使S.aureus的数量从5.322lgCFU/mL(空白)下降到3.441和3.563 lgCFU/mL;使S.agona的数量从6.094(空白)下降到3.813和3.830lgCFU/mL。

Regioselective Synthesis of Methyl β-D-galacopyranoside Derivatives and Biological Test against Bacterial Staphylococcus aureus and Salmonella agona

The glycoside fatty acid esters were synthesized with methyl β-D-galacopyranoside and fatty acid chloride using dibutyltin dimethoxide (DBDM) as the stannylating agent.The optimal reaction conditions were as follows:n(methyl β-D-galacopyranoside):n(DBDM):n(fatty acid chloride)=1:1.1:1.1,reaction temperature 25 ℃,the yields of methyl 3-O-acyl-β-D-galacopyranoside reach 70% or so.Biological tests against Staphylococcus aureus and Salmonella agona showed that methyl 3-O-lauroyl-β-D-galacopyranoside and methyl 3-O-myristoyl-β-D-galacopyranoside made the population of S. aureus reduce from 5.322 (water control) to 3.441 and 3.563 lgCFU/mL and the population of S. agona reduce from 6.094(water control) to 3.813 and 3.830 lgCFU/mL respectively.