本文選題：殼聚糖 + 化學(xué)改性　； 參考：《江南大學(xué)》2017年碩士論文

【摘要】：殼聚糖(CS)是自然界唯一存在的堿性多糖,因具有來源廣泛、生物相容性好、無毒無害等優(yōu)點而受到廣泛關(guān)注,同時殼聚糖還具有抗氧化、抑菌等生物活性,但由于其分子內(nèi)和分子間的氫鍵作用及結(jié)構(gòu)特點,導(dǎo)致殼聚糖的溶解性很差(酸性溶液除外),抑菌、抗氧化活性也相對較低,嚴(yán)重影響了殼聚糖在食品、醫(yī)藥、生物等領(lǐng)域的應(yīng)用。因此本課題通過化學(xué)改性,引入其他功能性基團來改善殼聚糖的性質(zhì)。本課題對殼聚糖進行了三種化學(xué)改性,得到了三種新的殼聚糖衍生物,通過傅里葉變換紅外光譜、核磁共振圖譜、X-射線衍射、元素分析等手段進行結(jié)構(gòu)解析。研究了殼聚糖衍生物的熱穩(wěn)定性、水溶性、抗氧化性、膽酸結(jié)合力和抑菌活性,主要結(jié)果如下:1.首先在TEMPO催化體系下將殼聚糖的C6位羥基氧化成羧基,再用3-氯丙酸在C2氨基上發(fā)生取代反應(yīng),分離純化后得到的衍生物即為N,O-羧基殼聚糖(NTCS),經(jīng)傅里葉變換紅外光譜、1H核磁共振圖譜、X-射線衍射確定產(chǎn)物的結(jié)構(gòu)。物性實驗結(jié)果表明N,O-羧基殼聚糖的熱穩(wěn)定性低于殼聚糖,在水中的溶解度為15.005 g/100 m L H2O,是原料殼聚糖溶解度(0.705 g/100 m L H2O)的近20倍,且粘度比殼聚糖低,總羧基含量為2.833 mmol/g�？寡趸瘜嶒灲Y(jié)果表明,N,O-羧基殼聚糖的DPPH自由基清除力、羥基自由基清除力和還原力均高于殼聚糖,體外膽酸結(jié)合力為17.209 mg/g,比殼聚糖的膽酸結(jié)合力(3.804 mg/g)高3.5倍。2.將殼聚糖C6羥基改性成氨基來改善殼聚糖的抑菌性。經(jīng)C2氨基鄰苯二甲�；�,C6羥基對甲苯磺�；�、疊氮化、還原,以及C2氨基脫保護后,得到6-氨基殼聚糖(NCS)。由紅外光譜、X-射線衍射和元素分析解析結(jié)構(gòu)。改性后衍生物的熱穩(wěn)定性降低,不同摩爾比(殼聚糖:4-甲苯磺酰氯=1:5、1:10、1:15)反應(yīng)得到的6-氨基殼聚糖的取代度分別為0.190、0.335、0.487�？寡趸瘜嶒灡砻�6-氨基殼聚糖具有更高的DPPH自由基清除力、羥基自由基清除力和還原力,1.2 mg/m L時的值分別為92.19%、62.81%、0.611。對大腸桿菌和金黃色葡萄球菌的抑菌實驗表明,氨基的引入增強了殼聚糖的抑菌性。3.以水溶性殼寡糖為原料,在其羥基上引入香草酸。甲烷磺酸既可以保護氨基,又是反應(yīng)的溶劑。首先香草酸的羧基酰氯化,然后與殼寡糖的羥基發(fā)生酯化反應(yīng),氨基脫保護后,得到香草酸-O-殼寡糖(VA-O-COS),由傅里葉變換紅外光譜、13C核磁共振圖譜、X-射線衍射表征結(jié)構(gòu)。研究發(fā)現(xiàn)香草酸-O-殼寡糖的結(jié)構(gòu)變得更加規(guī)整有序,熱穩(wěn)定性增強。香草酸和殼寡糖在不同摩爾比(1:2、1:3、1:5)下反應(yīng)得到的衍生物的取代度分別為0.750、0.912、1.064。衍生物的DPPH自由基清除力、羥基自由基清除力和還原力均有所改善,1.2 mg/m L時的值分別為85.46%、58.52%、0.733。抑菌試驗表明香草酸-O-殼寡糖對大腸桿菌和金黃色葡萄球菌的抑菌性均高于殼寡糖。結(jié)果表明,改性后得到的三種衍生物,其抗氧化性和抑菌活性(或膽酸結(jié)合力)均有所增強,為開發(fā)高效安全的殼聚糖類抗氧化劑、防腐抑菌劑等提供了新的思路。
[Abstract]:Chitosan (CS) is the only alkaline polysaccharide existing in nature. Because of its extensive sources, good biocompatibility, non-toxic and harmless advantages, chitosan has been widely concerned. At the same time, chitosan has the biological activity of antioxidation and bacteriostasis. However, the solubility of chitosan is very poor due to its intramolecular and intermolecular hydrogen bonding and structural characteristics. With the exception of the solution), the antibacterial activity and the antioxidant activity are relatively low, which seriously affect the application of chitosan in the fields of food, medicine, biology and so on. Therefore, this subject has been modified by chemical modification to improve the properties of chitosan. In this subject, three kinds of Chitosan were chemically modified and three new chitosan derivatives were obtained. The thermal stability, water solubility, antioxidation, cholic acid binding and antibacterial activity of chitosan derivatives were studied by Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, X- ray diffraction, and elemental analysis. The main results were as follows: 1. first, the C6 hydroxyl group of chitosan was oxidized to carboxyl group under the TEMPO catalytic system, and then the carboxyl group was oxidized to the carboxyl group. The substitution reaction of 3- chloro propionic acid on C2 amino group, the derivatives obtained after separation and purification are N, O- carboxyl chitosan (NTCS). The structure of the products is determined by Fourier transform infrared spectroscopy, 1H NMR spectrum and X- ray diffraction. The results of physical properties experiment show that the thermal stability of N, O- carboxyl chitosan is lower than that of chitosan, and the solubility in water is 1. 5.005 g/100 m L H2O is nearly 20 times the solubility of chitosan (0.705 g/100 m L H2O), and the viscosity is lower than chitosan and the total carboxyl content is 2.833 mmol/g. antioxidant experiment results. The scavenging force of DPPH radicals, the hydroxyl radical scavenging force and the return force of the N and O- carboxyl chitosan are higher than that of the chitosan, and the binding force of cholic acid in vitro is 17.209. The Bacteriostasis of chitosan was improved by modifying the chitosan C6 hydroxyl group by 3.5 times.2. (3.804 mg/g) to improve the Bacteriostasis of chitosan. After C2 amino phthalic two methylation, C6 hydroxyl toluene sulfonylation, azide, reduction, and C2 amino deprotection, 6- amino chitosan (NCS) was obtained. Infrared, X- ray diffraction and elemental analytical solutions were obtained. The thermal stability of the modified derivatives decreased, and the degree of substitution of different Molby (chitosan: 4- toluylsulfonyl chloride =1:5,1:10,1:15) was 0.190,0.335,0.487. antioxidant experiment, respectively, which showed that 6- amino chitosan had higher DPPH radical scavenging force, hydroxyl radical scavenging force and reducing force, 1.2 mg/ The values of M L were 92.19%, 62.81%, and 0.611. for Escherichia coli and Staphylococcus aureus. The antibacterial activity of Escherichia coli and Staphylococcus aureus showed that the introduction of amino group enhanced the antimicrobial activity of chitosan with water soluble chitosan oligosaccharides as raw material and the introduction of vanillic acid on its hydroxyl groups. Methane sulfonic acid could protect both amino and reaction solvents. First, the carboxyl chloride of oxalic acid. The structure of vanillin -O- shell oligosaccharide (VA-O-COS) was characterized by Fu Liye transform infrared spectroscopy, 13C NMR atlas and X- ray diffraction. The structure of -O- chitosan oligosaccharides was found to be more orderly and orderly, and the thermal stability was enhanced. Vanillin and chitosan oligosaccharides were found in the study. The degree of substitution of the derivatives under the different molar ratio (1:2,1:3,1:5) is the DPPH radical scavenging force of the 0.750,0.912,1.064. derivative, the hydroxyl radical scavenging force and the reducing force are improved, the values of the 1.2 mg/m L are 85.46%, 58.52%, respectively, and the bacteriostasis test of vanilla acid -O- shell oligosaccharides to Escherichia coli and Staphylococcus aureus The Bacteriostasis of Staphylococcus was higher than that of chitosan oligosaccharides. The results showed that the three derivatives obtained after modification had enhanced antioxidant and bacteriostasis activity (or cholic acid binding force), which provided new ideas for the development of efficient and safe chitosan antioxidant and antiseptic and bacteriostat.

【學(xué)位授予單位】：江南大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2017
【分類號】：O636.1

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