氨基双糖的制备及其生物活性研究

	氨基双糖的制备及其生物活性研究
	周婷婷 1,2
学位类型	硕士
导师	郭占勇
	2015-05-15
学位授予单位	中国科学院大学
学位授予地点	北京
学位专业	海洋化学
关键词	6-氨基-6-脱氧海藻糖 6-氨基-6-脱氧麦芽糖 6-氨基-6-脱氧纤维二糖抑菌活性抗氧化活性
摘要	氨基糖是一种重要的糖类，因为结构中氨基的存在使其具有许多独特的生理功能，如抑菌、抗氧化、抗肿瘤、增强免疫力等。氨基糖在自然界中广泛存在，但可用于工业化应用的不多。壳聚糖是自然界中储量仅次于纤维素的多糖甲壳素脱乙酰化之后的产物，其C-2位上氨基的存在赋予了壳聚糖更多的生理活性和反应性能。但是，壳聚糖在水和大部分有机溶剂中的溶解度都很低，这导致其应用范围受到了限制。双糖结构简单，分子量小，一般都可以溶于水，但氨基双糖在自然界中是不存在的，受壳聚糖启发，本文将氨基引入到双糖分子中，设计合成了6-氨基-6-脱氧海藻糖、6-氨基-6-脱氧麦芽糖和6-氨基-6-脱氧纤维二糖，并测试了三种氨基双糖的抑菌活性和抗氧化活性，探究氨基接入后对双糖分子生物活性的影响。三种氨基双糖的合成策略都是用叠氮基团作为亲核试剂取代接到双糖分子上的离去基团后将叠氮基还原得到氨基双糖。其中，氨基海藻糖和氨基麦芽糖合成使用溴基团作为离去基团，氨基纤维二糖的合成是以磺酸基作为离去基团，反应简单、高效，得到的三种氨基双糖都易溶于水。本文分别比较了海藻糖、麦芽糖、纤维二糖原料和其氨基衍生物的抑菌活性。结果表明，三种双糖原料均没有明显的抑菌活性，氨基引入后，双糖衍生物对大肠杆菌和金黄色葡萄球菌的抑制活性有了显著增加。其中，浓度为1 mg/mL的6-氨基-6-脱氧麦芽糖对金黄色葡萄球菌培养8 h的抑制率达到了52.33%，与同浓度阳性对照阿奇霉素对其的抑制率十分接近（54.9%）本文同时测试了双糖原料和其氨基衍生物的抗氧化活性。结果表明，三种双糖原料除了对羟自由基具有一定的清除能力外，还原能力和清除DPPH自由基、超氧阴离子自由基、过氧化氢的能力均不明显。当氨基接入后，抗氧化活性有了明显提高，且都随着浓度的升高而增加。本文制备的三种氨基双糖方法简单，抑菌活性和抗氧化活性与原料相比均有了明显提高，为氨基糖分子的构建和双糖的进一步开发利用提供了依据。
其他摘要	Amino saccharide is an important kind of carbohydrate, and it shows many unique biological activities such as antimicrobial, antioxidant, antitumor, and immunostimulatory properties. Amino saccharides are widely distributed in nature, but few of them can be used for industrial applications. Chitosan is the deacetylated product of chitin, which is abundant in nature. Chitosan shows more chemical reactivities and biological activities than chitin due to –NH₂ in C-2 position. However, chitosan is insoluble in water and most organic solvent, which has limited its application. Disaccharide have the advantages of simple structure, low molecular weight, and good solubility in water, which inspires us to introduce amino groups to disaccharide. In this study, we prepared 6-amino-6-deoxytrehalose, 6-amino-6-deoxymaltose, and 6-amino-6-deoxycellobiose and the antibacterial and antioxidant activities were assessed to explore the influence of amino groups on disaccharide. To prepare the three amino disaccharides, sodium azide was used as nucleophilic reagent to substitute leaving groups as azide could easily be reduced to amino groups. We used bromine groups to activate primary hydroxyl groups of trehalose and maltose and tosyl groups to activate primary hydroxyl groups of cellobiose as leaving groups. The reactions were convenient and efficient and the obtained products were soluble in water. The antibacterial activities of trehalose, maltose, cellobiose, and their amino derivatives against E. coli and S. aureus was comparatively studied. The results demonstrated that the three raw disaccharides barely showed inhibition against the tested pathogenic bacteria. The disaccharide derivatives exhibited obvious inhibition against E. coli and S. aureus due to the introducing of amino groups. At the concentration of 1 mg/mL, the inhibitory index of 6-amino-6-deoxymaltose against S. aureus was 52.33%, which was quite close to that of azithromycin (54.9%) when S. aureus was incubated for 8 h. The results of antioxidant experiments showed that reducing power and the scavenging effects of DPPH radical, superoxide radical, and hydrogen peroxide of the three raw disaccharides were not obvious. The antioxidant effect of disaccharide derivatives were stronger due to the introducing of amino groups. Meanwhile, the inhibitory effect of amino disaccharides was concentration related. The three amino disaccharides were synthesized in convenient ways and showed improved biological activities, which supplied theory thesis for the preparation of amino saccharides and further utilization of disaccharide.
语种	中文
文献类型	学位论文
条目标识符	http://ir.yic.ac.cn/handle/133337/7944
专题	中国科学院烟台海岸带研究所知识产出_学位论文
作者单位	1.中国科学院烟台海岸带研究所 2.中国科学院大学
第一作者单位	中国科学院烟台海岸带研究所
推荐引用方式 GB/T 7714	周婷婷. 氨基双糖的制备及其生物活性研究[D]. 北京. 中国科学院大学,2015.

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