CN115558005B - 一种cos-o-癸酰氯衍生物、制备方法及其应用 - Google Patents
一种cos-o-癸酰氯衍生物、制备方法及其应用 Download PDFInfo
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Abstract
本发明公开一种COS‑O‑癸酰氯衍生物、制备方法及其应用，COS‑O‑癸酰氯衍生物是以癸酰氯对壳寡糖羟基进行修饰所得的化合物；制备方法是按照如下步骤进行：称取定量的壳寡糖，在冰水浴条件下将壳寡糖溶解在甲烷磺酸中充分反应，得到壳寡糖甲烷磺酸盐溶液；将其加到NaOH溶液中，室温下搅拌反应至溶解，再按照壳寡糖与癸酰氯摩尔比为1：10‑30的比例逐滴加入癸酰氯继续反应1‑3h；加入氨水反应得到悬浮物，依次用无水乙醇和丙酮洗涤，冷冻干燥后得到COS‑O‑癸酰氯衍生物。COS‑O‑癸酰氯衍生物与壳寡糖相比，有效提高了对立枯丝核菌的抗菌性，可应用于制备防治水稻纹枯病药物。
Description
技术领域
本发明涉及一种壳寡糖衍生物、制备方法及其应用，尤其是一种COS-O-癸酰氯衍生物、制备方法及其应用。
背景技术
水稻纹枯病是水稻发生最为普遍的主要病害之一，是由立枯丝核菌侵染引起的一种真菌病害，往往造成谷粒不饱满、空壳率增加等现象，严重时可引起植株倒伏枯死，严重影响了水稻的种植。以往，对于水稻纹枯病都是采用农药进行防治，不仅会产生抗药性，还会导致水稻中农药残留，难以保障粮食安全。
壳寡糖（COS）是由壳聚糖通过酸水解、氧化法、物理法等方法降解而得到，是自然界中唯一带正电荷的碱性氨基低聚糖，聚合度为2-20。与壳聚糖相比，壳寡糖没有毒性，分子量低，水溶性更好。研究表明壳寡糖有抑菌活性，对细菌和真菌的生长繁殖有一定的抑制作用，但通常抑菌活性较弱。壳寡糖的结构比较特殊，其分子内含有活泼的氨基和羟基，容易进行化学反应，其中C2位的氨基和C3、C6位的羟基是活泼基团，这些活泼位点若引入其他的基团进行修饰，则可制备出不同的壳寡糖衍生物，从而改变壳寡糖的生物活性。然而，迄今为止并没有关于以壳寡糖为原料，利用癸酰氯进行化学修饰制备出COS-O-癸酰氯衍生物，以显著提高抑制立枯丝核菌的活性，从而应用于防治水稻纹枯病的相关报道。
发明内容
本发明是为了解决现有技术所存在的上述技术问题，提供一种COS-O-癸酰氯衍生物、制备方法及其应用。
本发明的技术解决方案是：一种COS-O-癸酰氯衍生物，其特征在于结构式如下：
。
一种上述COS-O-癸酰氯衍生物的制备方法，按照如下步骤进行：
步骤1. 称取定量的壳寡糖，在冰水浴条件下将壳寡糖溶解在甲烷磺酸中充分反应，得到壳寡糖甲烷磺酸盐溶液；
步骤2. 将壳寡糖甲烷磺酸盐溶液加到NaOH中，室温下搅拌反应至溶解，再按照壳寡糖与癸酰氯摩尔比为1：10-30的比例逐滴加入癸酰氯继续反应1-3h；
步骤3. 加入氨水反应得到悬浮物，依次用无水乙醇和丙酮洗涤，冷冻干燥后得到COS-O-癸酰氯衍生物。
一种上述COS-O-癸酰氯衍生物在制备防治水稻纹枯病药物中的应用。
本发明是以癸酰氯对壳寡糖羟基进行修饰，合成了COS-O-癸酰氯衍生物，与壳寡糖相比，有效提高了对立枯丝核菌的抗菌性，可应用于制备防治水稻纹枯病药物。本发明与传统化学修饰方法相比，具有操作简单、反应迅速等优点，反应均在室温（18-25℃）条件下进行，不仅节能还可避免衍生物结构遭受破坏。
附图说明
图1是本发明实施例COS-O-癸酰氯衍生物与壳寡糖的红外光谱图。
图2是本发明实施例COS-O-癸酰氯衍生物与壳寡糖的X-射线衍射图。
图3是本发明实施例所用原料壳寡糖的1H核磁共振图。
图4是本发明实施例COS-O-癸酰氯衍生物的1H核磁共振图。
图5是本发明实施例COS-O-癸酰氯衍生物与壳寡糖、无菌水的抗立枯丝核菌图。
具体实施方式
本发明的COS-O-癸酰氯衍生物的制备方法，按照如下步骤进行：
步骤1.称取0.005mol壳寡糖（COS），在冰水浴条件下溶解在7.5g的甲烷磺酸中反应2h，形成壳寡糖甲烷磺酸盐溶液；
步骤2. 将壳寡糖甲烷磺酸盐溶液加到浓度为40%w/v的NaOH中，室温下搅拌反应3h至溶解，再按照壳寡糖与癸酰氯质量比为1：20的比例逐滴加入19.07g癸酰氯继续反应3h，则改性产物出现；
步骤3. 加入氨水反应3h得到悬浮物，依次用无水乙醇和丙酮洗涤3遍，冷冻干燥后得到COS-O-癸酰氯衍生物，命名为COS-C10。
实施例所用原料均为市售商品，其中壳寡糖聚合度为2-50，脱乙酰度至少为90%；癸酰氯分子式为C10H19ClO，分子量为190.71。
反应式如下：
。
实验：
一. 本发明实施例所用原料壳寡糖及所得COS-O-癸酰氯衍生物（COS-C10）的光谱分析
将本发明实施例所用的壳寡糖（COS）和制得的COS-O-癸酰氯衍生物（COS-C10）分别与溴化钾按照质量比为1：100进行混合研磨，采用溴化钾压片法进行红外光谱的测定，扫描范围4000-400 cm-1，扫描次数为72次，分辨率4 cm-1，红外光谱如图1所示。
从图1可以看出，3400cm-1处的宽峰为N-H和O-H伸缩振动的叠加吸收峰，为壳寡糖的特征峰。与壳寡糖相比，COS-C10在3400cm-1处O-H伸缩振动明显减弱，证明-OH参与了反应，1560cm-1和1435cm-1处的一组新吸收峰，证明有羰基酯形成，改性后的衍生物在2960-2850 cm-1处出现了更强的吸收峰，为C-H的伸缩振动，1520 cm-1处N-H的伸缩振动仍然存在，以上说明壳寡糖的羟基成功引入了癸酰氯。
二. 本发明实施例所用原料壳寡糖及所得COS-O-癸酰氯衍生物（COS-C10）的XRD分析
将本发明实施例所用的壳寡糖（COS）和制得的COS-O-癸酰氯衍生物（COS-C10）分别研磨后加入无水乙醇平铺在硅板上，待无水乙醇挥发后再进行XRD分析测样，扫描条件为Cu靶，扫描温度25℃，扫描速度4°/ min，扫描范围5-80°，X-射线衍射图如图2所示。
从图2可以看出，壳寡糖分别在2θ=9°和2θ=21.5°有两个衍射吸收峰，这与壳寡糖分子的晶体形态有关系；经过改性后的壳寡糖衍生物（COS-C10），其X-射线衍射图最大衍射角出峰位置向右偏移，并且最大衍射角峰强度提高。在2θ=30°、40°、45°、56°和75°处都出现了新的吸收峰，说明加入癸酰氯后，改变了壳寡糖的晶型。
三. 本发明实施例所用原料壳寡糖及所得COS-O-癸酰氯衍生物（COS-C10）的核磁共振氢谱分析
称取微量的壳寡糖（COS）及COS-O-癸酰氯衍生物（COS-C10）转移到核磁管中，使用移液枪将DMSO-d6转移到核磁管中，震荡至充分溶解后进行氢谱测定。
COS1H核磁共振图和COS-C101H核磁共振图分别如如图3、图4所示。从图3、图4可以看出：δ=1.91ppm处的吸收峰是壳寡糖未脱尽的乙酰基上甲基的化学位移，δ=3.0-3.75ppm是壳寡糖糖环上氨基葡萄糖H和N-乙酰氨基葡萄糖残基上H的化学位移，为壳寡糖的特征峰，δ=2.51ppm处为溶剂的吸收峰。与壳寡糖相比，COS-O-癸酰氯衍生物在δ=0.86ppm时出现新的化学位移，为酰基链末端甲基（-CH3）的化学位移，属于衍生物的特征峰，δ=1.80ppm处的氨基葡萄糖残基上质子的化学位移没有变化仍然存在，说明壳寡糖的羟基与癸酰氯发生了反应。核磁结果与红外结果一致，表明成功合成COS-O-癸酰氯衍生物。
四. 本发明实施例所用原料壳寡糖及所得COS-O-癸酰氯衍生物（COS-C10）的抗立枯丝核菌活性
点接法将立枯丝核菌（中国农业微生物菌种保藏管理中心，ACCC 36246）接到培养基中，25℃培养。
将样品（本发明实施例所用原料壳寡糖及所得COS-O-癸酰氯衍生物）分别与培养基混合配置成2 mg/mL、1 mg/mL、0.5 mg/mL、0.25 mg/mL、0.125 mg/mL、0 mg/mL的浓度的含药平板并以加入等体积水的培养基为空白对照（CK），用0.7cm的打孔器在培养好的目的菌株培养基上取菌饼，放在药板中央，菌丝面朝下，25℃培养箱中培养，十字交叉法测量菌丝生长直径，使用Excel软件计算抑菌率，每个处理重复三次。
菌丝生长抑菌率(100%)=（对照菌落直径-处理菌落直径）/ （对照菌落直径-0.7cm）×100%
实验结果如图5及表1所示。
表1
本发明实施例所得COS-O-癸酰氯衍生物对立枯丝核菌具有较强的抗菌活性，抑菌率明显高于壳寡糖，可应用于制备防治水稻纹枯病药物。
Claims (3)
1.一种COS-O-癸酰氯衍生物，其特征在于结构式如下：
所述n=2-50。
2.一种如权利要求1所述COS-O-癸酰氯衍生物的制备方法，其特征在于按照如下步骤进行：
步骤1. 称取定量的壳寡糖，所述壳寡糖聚合度为2-50、脱乙酰度至少为90%，在冰水浴条件下将壳寡糖溶解在甲烷磺酸中充分反应，得到壳寡糖甲烷磺酸盐溶液；
步骤2. 将壳寡糖甲烷磺酸盐溶液加到NaOH中，室温下搅拌反应至溶解，再按照壳寡糖与癸酰氯摩尔比为1：10-30的比例逐滴加入癸酰氯继续反应1-3h；
步骤3. 加入氨水反应至得到悬浮物，依次用无水乙醇和丙酮洗涤，冷冻干燥后得到COS-O-癸酰氯衍生物。
3.一种如权利要求1所述COS-O-癸酰氯衍生物在制备防治水稻纹枯病药物中的应用。
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