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N-酰基高丝氨酸内酯半抗原衍生物及其全抗原的合成与鉴定 被引量:1

The synthesis and identification of N-acyl-homoserine lactone hapen derivant and holoantigen
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摘要 目的本研究旨在合成N-酰基高丝氨酸内酯(N-acyl-homoserine lactone,AHL)全抗原,为建立AHL免疫检测新方法奠定基础。方法以γ-丁内酯和高丝氨酸内酯为原料,经保护、缩合、脱保护、氧化等一系列反应,获得N-丁酰高丝氨酸内酯、N-己酰高丝氨酸内酯和含有化学交联活性基团的羧基丁酰高丝氨酸内酯半抗原衍生物,用核磁共振氢谱和质谱方法进行结构确证,并采用活泼酯法合成N-酰基高丝氨酸内酯全抗原。结果质谱与核磁共振氢谱分析结果与理论预测相同,表明成功合成目标产物N-丁酰(己酰)高丝氨酸内酯和羧基丁酰高丝氨酸内酯半抗原衍生物;紫外吸收光谱扫描结果显示半抗原AHL已分别与载体牛血清白蛋白和鸡卵白蛋白交联,成功制备其全抗原。结论本实验成功合成了N-酰基高丝氨酸内酯半抗原衍生物和全抗原,为制备AHL相应抗体奠定了基础。 Objective The research is to aim at synthesis of N-acyl-homoserine lactone (AHL) holoantigen, to provide basis for establishment of new method in AHL immunodetection. Methods Having used gamma-butyrolactone and homoserine lactone as the starting materials,synthe- sized N-butyryl homoserine lactone, N-caproyl homoserine lactone and N-4-carboxy-butyryl homo- serine lactone hapten derivant having chemical crosslinking active group by serial reactions such as protection, condensation, deprotection and oxidation. The obtained samples were characterized by ~H- nuclear magnetic resonance (tH-NMR) and liquid chromatography coupled mass spectrum (LCMS), and synthesized N-acylhomoserine lactone holoantigen by the method of active ester. Results The HNMR and LCMS results revealed that the obtained compound were the target product of N-butyryl (caproyl) homoserine lactone and γ-carboxy homoserine lactone hapten derivant, just alike as the prediction. The ultraviolet absorption spectrum results revealed that hapten AHL had crosslinked with BSA and OVA, AHL holoantigen had been prepared well. Conclusion This experiment succeeded in synthesis of N-acylhomoserine lactone hapten derivant and holoantigen, and provide the basis work of preparation of the corresponding antibodies of AHL.
出处 《转化医学杂志》 2013年第6期348-351,共4页 Translational Medicine Journal
基金 海军总医院科研创新基金课题资助(CX201201)
关键词 Γ-丁内酯 高丝氨酸内酯 N-酰基高丝氨酸内酯 半抗原衍生物 Gamma-butyrolactone Homoserine lactone N-acyl-homoserine lactone (AHL) Hapten derivant
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