苯甲酸乙酰氨基葡萄糖酯的合成及抑菌性能研究

于沛沛; 王斌; 李婧茹; 姜启兴; 许艳顺; 刘晓丽; 杨方; 夏文水

doi:10.13386/j.issn1002-0306.2018.19.010

苯甲酸乙酰氨基葡萄糖酯的合成及抑菌性能研究

Synthesis and Antibacterial Activity of Benzoyl NAG Ester

摘要

摘要: 以N-乙酰氨基葡萄糖和苯甲酰氯为原料,进行酯化反应,合成了苯甲酸乙酰氨基葡萄糖酯,用红外光谱、液质联用证实了其分子结构,并分析了产物的溶解性、熔点及抑菌活性。结果表明,在反应温度0 ℃、反应时间3 h,苯甲酰氯/N-乙酰氨基葡萄糖摩尔比为4:1时,经提纯得到合成产物,合成产物主要为三酯。该产物在多种有机溶剂中都具有良好的溶解性;其熔点温度为171~175 ℃;抑菌活性随浓度升高逐渐增强,在pH3.5~7.5范围内均有较好的抑菌效果,在不同pH时,其对大肠杆菌、金黄色葡萄球菌、啤酒酵母、黑曲霉的最低抑菌浓度(MIC)范围分别为2.4~2.6、1.4~1.6、2.0~2.2、1.8~2.0 g/L。

Abstract: Benzoyl N-Acetyl-D-Glucosamine (NAG) ester was synthesised based on NAG and benzoyl chloride. The chemical structure of the products were characterized by FT-IR, LC-MS. The solubility, thermal stability and antibacterial activity were also studied. Research showed that the tri-ester was synthesized with the molar ratio of reagents at 4:1 (benzoyl chloride/NAG) under the reaction temperatureat at 0℃ for 3h. The benzoyl NAG ester had good solvability in various organic solvents and the melting temperature was about 171~175℃. Moreover, the antibacterial activity was concentration-dependent and varying pH had little effect on antibacterial activity. The inhibitory experiments showed that benzoyl NAG ester had significant effect against the growth of microorganisms under the pH rang from3.5 to 7.5.The minimum inhibitory concentration (MIC) of benzoyl NAG ester against E. coli, staphylococcus aureus, beer yeast, aspergillus Niger were 2.4~2.6, 1.4~1.6, 2.0~2.2, 1.8~2.0 g/L, respectively.