DMTMM-mediated grafting reaction of glucuronic acid on chitosan,Journal of Applied Polymer Science

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DMTMM-mediated grafting reaction of glucuronic acid on chitosan
Journal of Applied Polymer Science ( IF 2.7 ) Pub Date : 2022-11-09 , DOI: 10.1002/app.53318
Aoqi Li ₁ , Yingqing Ye ₂ , Peixin Gong ₂ , Bo Xiao ₁ , Bo Jiang ₁

Affiliation

Compared with traditional conjugates 1-ethyl-3-(3-dimethyl aminopropyl) carbodiimide (EDC) and N-hydroxysuccinimide (NHS), 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) is an emerging biological coupling reagent and has been used in the amidation of hyaluronic acid. In this paper, DMTMM was used to achieve the amidation of chitosan (CS) with glucuronic acid (GA) in an aqueous medium to generate a GA-CS derivative. The grafting efficacy was preliminarily compared with the EDC/NHS-mediated reaction. As a result, the substitution degree of 17.6% for DMTMM-mediated grafting and 13.1% for EDC/NHS chemistry indicated that DMTMM-mediated synthesis of GA-CS appeared to be more efficient. The reaction kinetics experiments showed that GA-CS derivative with a degree of substitution up to about 26.1% was obtained using equal molar ratios of DMTMM and GA exceeding CS at room temperature. These results indicate that employing DMTMM as a coupling agent is a feasible and promising strategy for the amidation modification of chitosan.

中文翻译：

DMTMM介导的葡萄糖醛酸在壳聚糖上的接枝反应

与传统偶联物 1-乙基-3-(3-二甲氨基丙基) 碳二亚胺 (EDC) 和 N-羟基琥珀酰亚胺 (NHS) 相比，4-(4,6-二甲氧基-1,3,5-三嗪-2-基)- 4-甲基吗啉氯化物 (DMTMM) 是一种新兴的生物偶联剂，已用于透明质酸的酰胺化。在本文中，DMTMM 用于实现壳聚糖 (CS) 与葡萄糖醛酸 (GA) 在水性介质中的酰胺化，生成 GA-CS 衍生物。嫁接效果初步与 EDC/NHS 介导的反应进行了比较。结果，DMTMM 介导的接枝取代度为 17.6%，EDC/NHS 化学取代度为 13.1%，表明 DMTMM 介导的 GA-CS 合成似乎更有效。反应动力学实验表明，GA-CS衍生物的取代度可达26左右。在室温下使用超过 CS 的等摩尔比的 DMTMM 和 GA 获得 1%。这些结果表明，使用 DMTMM 作为偶联剂对壳聚糖进行酰胺化修饰是一种可行且有前途的策略。

更新日期：2022-11-09

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