油酸和十二烷二酸的氨基酸酯合成及其抗菌性

Synthesis and antibacterial activities of amino acid esters from oleic acid and dodecanedioic acid

以L-丙氨酸乙酯盐酸盐、甘氨酸乙酯盐酸盐、L-蛋氨酸甲酯盐酸盐、L-亮氨酸乙酯盐酸盐和L-酪氨酸甲酯盐酸盐在1-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐和1-羟基苯并三唑(HOBt)的作用下分别与油酸进行反应,生成了5种油酸的氨基酸衍生物;将L-丙氨酸乙酯盐酸盐和甘氨酸乙酯盐酸盐分别与十二烷二酸进行反应,生成了两种十二烷二酸的氨基酸衍生物,7种产物的收率均≥75%。利用FTIR、TGA、1HNMR和LC-MS对产物进行了表征,测试了产物的水油分散性,考察了产物对金黄色葡萄球菌和大肠杆菌的抑菌性。结果表明,所合成的脂肪酰氨基酸酯均能在水油体系中分散,且具有较强的生物抗菌性,其中,0.01 mg油酸酰亮氨酸乙酯能有效地抑制金黄色葡萄球菌(菌数由2.0×109CFU/mL降至1.4×10^(7)CFU/mL),而相同质量油酸酰酪氨酸甲酯则能抑制大肠杆菌(菌数由2.0×10^(9)CFU/mL降至1.8×10^(7)CFU/mL)。

Five types of oleic acid derivatives were produced by reaction of oleic acid with L-alanine ethyl ester hydrochloride,glycine ethyl ester hydrochloride,L-methionine methyl ester hydrochloride,L-leucine ethyl ester hydrochloride and L-tyrosine methyl ester hydrochloride,respectively,in presence of1-ethyl-(3-dimethyllaminopropyl)carbodiie hydrochlide and 1-hydroxybenzotriazole.In addition,two types of dodecanedioic acid derivatives were also synthesized via reactions of dodecanedioic acid with L-alanine ethyl ester hydrochloride and glycine ethyl ester hydrochloride,respectively.It was found that the yields of all seven products were higher than or equal 75%.The structures of the products obtained were then characterized by FTIR,TGA,~1HNMR and LC-MS,followed by evaluations on the dispersibilities and the antibacterial activities against Staphylococcus aureus and Escherichia coli.The results showed that these fatty acid acyl amino acid esters exhibited good dispersity in both aqueous and organic phases,and obvious antimicrobial activities.Oleoyl leucine ethyl ester (0.01 mg) could effectively inhibit the growth of Staphylococcus aureus (the number of bacteria was decreased from 2.0×10^(9) CFU/mL to 1.4×10^(7) CFU/mL),while oleoyl tyrosine methyl ester with the same mass showed significant growth inhibition effect on Escherichia coli (the number of bacteria was decreased from 2.0×10^(9) CFU/mL to 1.8×10^(7) CFU/mL).