油酸和十二烷二酸的氨基酸酯的合成及其生物抗菌性

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2.0×10⁹ CFU/mL降至1.4×10⁷ 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2.0×10⁹ CFU/mL降至1.8×10⁷ CFU/mL)。

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

Glycine ethyl ester hydrochloride, L-Alanine ethyl ester hydrochloride, L-leucine ethyl ester hydrochloride, L-methionine methyl ester hydrochloride and L-tyrosine methyl ester hydrochloride were used to react with oleic acid in presence of EDC/HOBt to produce five kinds of amino acid derivatives of oleic acid. In addition, glycine ethyl ester hydrochloride and L-alanine ethyl ester hydrochloride were reacted with dodecanedioic acid to produce two amino acid derivatives of dodecanedioic acid. The results showed that seven products were synthesized with yields higher than 75%. The structures of the products were characterized by FTIR, TGA, 1HNMR and LC-MS. The dispersibilities of the products were tested, and the antibacterial activities of the products against Staphylococcus aureus and Escherichia coli were investigated. The results showed that the products were capable of dispersing in both aqueous and organic phases. Moreover, these fatty acid acyl amino acid esters showed obvious antimicrobial activities. The oleoyl leucine ethyl ester can effectively inhibit the growth of Staphylococcus aureus (the number of bacteria is decreased from 2×109 CFU/mL to 1.4×107 CFU/mL). The oleoyl tyrosine methyl ester can inhibit Escherichia coli (the number of bacteria is decreased from 2×109 CFU/mL to 1.8×107 CFU/mL).