香叶醇烷基改性壳寡糖的高效制备及表征

Facile Synthesis and Characterization of Geraniol Alkyl Modified Chitosan Oligosaccharides

摘要:

在之前研究的基础上，改进实验方案，提高香叶醇接枝壳寡糖衍生物的产率。通过香叶醇溴化和取代反应两步合成香叶醇烷基改性的壳寡糖COS-M-Ger1、COS-M-Ger2和COS-M-Ger3，与之前的研究相比产率提高4~7倍。紫外可见吸收光谱、傅立叶红外光谱、核磁氢谱、元素分析等表征手段表明产物成功合成，产物的取代度为0.260~0.283；溶解性、X-衍射和热稳定性研究表明，与香叶醇相比产物在酸性和中性条件下有较好的溶解性；相较壳寡糖，产物的结晶度较强而热稳定性较差；平板抗菌结果表明衍生物COS-M-Ger1、COS-M-Ger2和COS-M-Ger3的抑菌性优于壳寡糖和两种市售抗菌剂；本研究为溶解性好、高效抗菌的壳寡糖衍生物的大批量生产提供理论研究基础。

Abstract:

The yield of geraniol-modified chitosan oligosaccharide (COS-M-Ger) derivatives was increased based on the improvement of experimental scheme described in previous research. COS-M-Ger1，COS-M-Ger2 and COS-M-Ger3 were synthesized through a two-step reaction of geraniol bromination and substitution, and the yield was 4~7 times higher than that of the previous study. The products were characterized by UV-Vis, FT-IR, 1H-NMR and elemental analysis to confirm the successful synthesis, and the substitution degrees of products were in the range from 0.260 to 0.283. Solubility, X-ray diffraction analysis and TGA showed that the products had better solubility than Ger under acidic and neutral conditions. Compared to COS, the crystallinity of product was stronger, however, the thermal stability was worse. The antibacterial results showed that the antibacterial effects of COS-M-Ger1，COS-M-Ger2 and COS-M-Ger3 were better than those of COS and two commercially available antibacterial agents. This paper provides a theoretical basis for the mass production of COS derivatives with good solubility and high antibacterial effect.