碱性离子液体条件下烷基化壳聚糖衍生物的制备及其抑菌性能研究

doi:10.3969/j.issn.0253-2417.2014.03.008

林产化学与工业 ›› 2014, Vol. 34 ›› Issue (3): 44-50.doi: 10.3969/j.issn.0253-2417.2014.03.008

碱性离子液体条件下烷基化壳聚糖衍生物的制备及其抑菌性能研究

裴立军¹, 蔡照胜², 商士斌¹, 宋湛谦¹

1. 中国林业科学研究院林产化学工业研究所;生物质化学利用国家工程实验室;国家林业局林产化学工程重点开放性实验室;江苏省生物质能源与材料重点实验室, 江苏南京 210042;
2. 盐城工学院化学与生物工程学院, 江苏盐城 224051

收稿日期:2013-05-06 出版日期:2014-06-25 发布日期:2014-06-25
通讯作者: 宋湛谦，中国工程院院士，研究员，博士生导师，主要从事天然产物化学研究；E-mail：songzq@hotmail.com。 E-mail:songzq@hotmail.com
作者简介:裴立军（1980- ），男，山东潍坊人，博士生，主要从事天然资源化学与利用
基金资助:
国家自然科学基金资助项目（31170543）

Synthesis and Antibacterial Activity of Alkylated Chitosan Derivatives under Basic Ionic Liquid Condition

PEI Li-jun¹, CAI Zhao-sheng², SHANG Shi-bin¹, SONG Zhan-qian¹

1. Institute of Chemical Industry of Forest Products, CAF;National Engineering Lab. for Biomass Chemical Utilization;Key and Open Lab. of Forest Chemical Engineering, SFA;Key Lab. of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China;
2. School of Chemical and Biological Engineering, Yancheng Institute of Technology, Yancheng 224051, China

Received:2013-05-06 Online:2014-06-25 Published:2014-06-25

摘要/Abstract

摘要： 壳聚糖（CTS）首先用1-甲基-3-丁基咪唑氢氧化物（[Bmim]OH）碱性离子液体碱化，再令碱化后壳聚糖与卤代烷进行烷基化反应，制备具有不同长度取代基的烷基化壳聚糖，用FT-IR、 ¹H NMR 对烷基化产物进行了表征，并考察了时间、温度及物料比对烷基壳聚糖取代度的影响，得到较佳的反应条件。离子液体具有重复使用性，反应后的离子液体重复使用3次后，烷基壳聚糖的取代度仍无明显降低。采用最低抑菌浓度法对目标产物的抑菌性能进行了测试，初步的结果显示合成的化合物都有一定的抑菌活性，特别是乙烷基壳聚糖（E-CTS）、丁烷基壳聚糖（B-CTS）及十二烷基壳聚糖（D-CTS）都对绿脓假单胞菌具有良好的活性，对其最低抑菌浓度分别为128、128和256 mg/L，抑菌效果优于市售杀菌剂氨共青霉素钠，十六烷基壳聚糖（C-CTS）的抑菌效果较差。烷基化合物的抑菌性能随取代度增大或碳链的增长均有所降低。

关键词: 碱性离子液体, 碱化, 烷基化, 抑菌性能

Abstract: Chitosan (CTS) was alkalized by [Bmim]OH basic ionic liquid in this study. Then the alkalized chitosan reacted with alkyl halides to prepare the alkylated chitosan with different substituents. The structures of alkylated products were characterized by IR and ¹H NMR. The effects of reaction time, temperature and material ratio on the substitution degree (D_S) of alkyl chitosan were also investigated and then the optimal reaction condition was obtained. The separated ionic liquid could be reused,and no noticeable changes of the D_S for alkylated chitosan were observed when the reacted ionic liquid was reused for 3 times. The antibacterial properties of the target products were tested by the minimum inhibitory concentration method. Preliminary results indicated that those compounds had the antibacterial activity. In particular, ethyl chitosan(E-CTS), butyl chitosan(B-CTS), and dodecyl chitosan(D-CTS) exhibited excellent antibacterial activities against to Pseudomonas aeruginosa. The minimum inhibition concentration were 128,128 and 256 mg/L, respectively. Their antibacterial effects were better than commercially sold Ampicillin sodium while the C-CTS antibacterial effect was worse. The antibacterial activity of alkylated chitosan decreased with the increase of the D_S and the length of carbon chain.

Key words: basic ionic liquid, alkalization, alkylation, antibacterial activity

中图分类号:

TQ35
O636.1

裴立军, 蔡照胜, 商士斌, 宋湛谦. 碱性离子液体条件下烷基化壳聚糖衍生物的制备及其抑菌性能研究[J]. 林产化学与工业, 2014, 34(3): 44-50.

PEI Li-jun, CAI Zhao-sheng, SHANG Shi-bin, SONG Zhan-qian. Synthesis and Antibacterial Activity of Alkylated Chitosan Derivatives under Basic Ionic Liquid Condition[J]. Chemistry and Industry of Forest Products, 2014, 34(3): 44-50.

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碱性离子液体条件下烷基化壳聚糖衍生物的制备及其抑菌性能研究

Synthesis and Antibacterial Activity of Alkylated Chitosan Derivatives under Basic Ionic Liquid Condition

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