CN1680571A - 麦芽三糖的制备方法 - Google Patents
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Abstract
本发明公开的技术方案是提供一种麦芽三糖的制备方法，其方法包括以下步骤：1)由出芽孢梗霉发酵产生的胞外多糖普鲁兰多糖(Pullulan)为原料，利用普鲁兰多糖中α－(1→6)－葡萄糖苷键比α－(1→4)－葡萄糖苷键易于断裂，使之在酸与醋酸酐混合液中发生乙酰解，其比例为：1∶100－1∶10；反应温度为－10℃－+50℃获得全乙酰化的麦芽三糖；2)以pH＝9－10的碱强度水解掉乙酰基；3)经普通反相柱层析过程制得麦芽三糖纯品。本发明的效果是由普鲁兰多糖可大量制备医药级的麦芽三糖，简化麦芽三糖的制备，对于急性胰腺疾病快速诊断试剂的生产以及具有药用前景的糖类化合物的开发都具有重要意义。
Description
技术领域
本发明涉及麦芽三糖的一种制备方法。
背景技术
麦芽三糖是三个葡萄糖以α-(1→4)连接形成的寡糖，麦芽糖酶可以淀粉或原粮(如碎米等)为原料，经不完水解而形成的麦芽三糖至八糖的混合物。通常麦芽三糖都是通过发酵的方式来获得，但通过发酵法制备试剂级纯度的麦芽三糖仍然很困难。
麦芽三糖可通过转糖苷作用生成含有α-(1→6)键的异麦芽糖、潘糖和其它带分枝的低聚糖，对清除宿便、抑制肠道腐败细菌、调节肠道健康能起到巨大作用。
对诊断急性胰腺疾病来说，测定人血清中的胰淀粉酶活性是最实用和最灵敏的方法。在过去的十数年间，科学工作者们发明了上百种检测方法(Clinical Chemistry，1982，28，2201-2205)，其核心都是对灵敏底物的研发，这些底物由糖和生色基团组成。但大多数分析方法都需要糖部分的复杂修饰，以抵消此测量法中的辅助酶(α-葡萄糖苷酶)对底物水解而造成的影响。最新的研究成果表明：由麦芽三糖与2-氯-4-硝基酚组成的底物最适用于急性胰腺疾病的快速诊断(Clinica Chimica Acta，1998，272，137-147；ClinicalChemistry，2000，46，928-933)。因此，简易麦芽三糖的制备在本诊断试剂的生产中具有重要意义。
发明内容
为解决上述技术中的问题，本发明的目的是提出一种用合成方法来制备目标分子的麦芽三糖的制备方法。
为实现上述发明目的，本发明公开的技术方案是提供一种麦芽三糖的制备方法，其方法包括以下步骤：
1)由出芽孢梗霉发酵产生的胞外多糖普鲁兰多糖(Pullulan)为原料，利用普鲁兰多糖中α-(1→6)-葡萄糖苷键比α-(1→4)-葡萄糖苷键易于断裂，使之在酸与醋酸酐混合液中发生乙酰解，其比例为：1∶100-1∶10；反应温度为-10℃-+50℃获得全乙酰化的麦芽三糖；
2)以pH＝9-10的碱强度水解掉乙酰基；
3)经普通反相柱层析过程制得麦芽三糖纯品。
所述的乙酰解含有冰乙酸，含量可达体积比为10-50％。
所述酸为浓硫酸、无水氯化锌、三氟乙酸之一种。
所述酸为浓硫酸、无水氯化锌、三氟乙酸之一种与冰乙酸的混合物。
所述水解掉乙酰基条件为室温下氨气饱和的甲醇溶液或pH值9-10的甲醇钠-甲醇溶液。
本发明的效果是由普鲁兰多糖可大量制备医药级的麦芽三糖，简化麦芽三糖的制备，对于急性胰腺疾病快速诊断试剂的生产以及具有药用前景的糖类化合物的开发都具有重要意义。
具体实施方式
结合实施例对本发明的麦芽三糖的制备方法加以说明。
本发明的麦芽三糖的制备方法其核心是由普鲁兰多糖经乙酰解，从而获得全乙酰化的麦芽三糖；全乙酰化的麦芽三糖经脱乙酰制得麦芽三糖纯品。
普鲁兰多糖(Pullulan)中文亦译为茁霉多糖、出芽短梗孢糖、普聚多糖或普鲁兰糖。它是出芽孢梗霉产生的胞外多糖，以α-(1→6)糖苷键结合麦芽糖构成同型多糖为主，即葡萄糖按α-(1→4)糖苷键结合成麦芽三糖，两端再以α-(1→6)-糖苷键同另外的麦芽三糖结合，如此反复连接而成高分子多糖。
本发明麦芽三糖的制备方法的实现过程如下：
1、在250毫升圆底烧瓶中，将普鲁兰多糖(pullulan)15g溶于乙酸酐50ml和吡啶75ml的混合液中，置于60℃的恒温浴中搅拌两天，将溶剂在BUCHI旋转蒸发仪上减压蒸干，然后将此蒸干的粘稠胶状体倒入稀盐酸(1N，300ml)水溶液中搅拌30分钟后，抽滤，用大量水洗，并用饱和的碳酸氢钠饱和溶液洗，直至弱碱性为止，50℃下烘干，碾碎得白色固体粉末状全乙酰普鲁兰多糖粗品23克(含量大约60-80％)。
2、在100毫升圆底烧瓶中，上述全乙酰普鲁兰多糖15克溶于含有5％浓硫酸的乙酸酐溶液中(体积比)，也可用无水氯化锌或三氟乙酸，含量1％-10％，置于40℃的恒温浴中搅拌三天，后倒入300ml冰水中，用乙酸乙酯萃取三次，再用饱和碳酸氢钠洗涤萃取，直至中性。浓缩后用柱色谱梯度分离，先以乙酸乙酯/石油醚2∶1进行粗分，再以乙酸乙酯/石油醚1∶1作为洗脱剂分离，以薄层色谱(TLC)检测，可得全乙酰麦芽三糖纯品5.5克(含量大于98％)。未反应完的原料可用乙酸乙酯/甲醇4∶1作为洗脱剂回收。
3、将30克全乙酰普鲁兰多糖溶于含有浓硫酸、冰乙酸和乙酸酐的混合溶液中体积比1∶10∶20，在0℃下反应7天，后倒入400ml水中用乙酸乙酯萃取三次，再用饱和碳酸氢钠洗涤萃取，直至中性。浓缩后用柱色谱梯度分离，先以乙酸乙酯/石油醚2∶1进行粗分，再以乙酸乙酯/石油醚1∶1作为洗脱剂分离，得全乙酰麦芽三糖10克。
4、脱乙酰条件为室温下，氨气饱和的甲醇溶液或pH值9-10的甲醇钠-甲醇溶液(对应权5)，即，在250毫升圆底烧瓶中，将全乙酰麦芽三糖5克溶于100毫升无水甲醇中，加入1N的甲醇钠-甲醇溶液至pH10，室温下反应10小时，阳离子交换树脂(Amberlitel20H+)中和后，减压蒸干得麦芽三糖粗品(含量大于90％)。
5、将上述麦芽三糖粗品3克，溶于2毫升水中，在葡聚糖凝胶G25柱上以去离子水作溶剂除盐纯化，含有麦芽三糖的流动相在标准方法下冷冻干燥后得麦芽三糖纯品(在反相高压液相标准条件下，纯度大于99.5％)。
Claims (5)
1、一种麦芽三糖的制备方法，其方法包括以下步骤：
1)由出芽孢梗霉发酵产生的胞外多糖普鲁兰多糖为原料，利用普鲁兰多糖中α-(1→6)-葡萄糖苷键比α-(1→4)-葡萄糖苷键易于断裂，使之在酸与醋酸酐混合液中发生乙酰解，酸与醋酸酐的比例为：1∶100-1∶10；反应温度为-10℃-+50℃获得全乙酰化的麦芽三糖；
2)以pH＝9-10的碱强度水解掉乙酰基；
3)经普通反相柱层析过程制得麦芽三糖纯品。
2、根据权利要求1所述的制备方法，其特征是：所述的乙酰解含有冰乙酸，含量可达体积比为10-50％。
3、根据权利要求1所述的制备方法，其特征是：所述酸为浓硫酸、无水氯化锌、三氟乙酸之一种。
4、根据权利要求1所述的制备方法，其特征是：所述酸为浓硫酸、无水氯化锌、三氟乙酸之一种与冰乙酸的混合物。
5、根据权利要求1所述的制备方法，其特征是：所述水解掉乙酰基条件为室温下氨气饱和的甲醇溶液或pH值9-10的甲醇钠-甲醇溶液。
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101438782B (zh) * | 2008-12-31 | 2011-04-13 | 保龄宝生物股份有限公司 | 一种保湿糖浆及其制备方法 |
| CN105713051A (zh) * | 2014-12-04 | 2016-06-29 | 中国科学院生态环境研究中心 | 一种制备麦芽三糖的新方法 |
| US10568839B2 (en) | 2011-01-11 | 2020-02-25 | Capsugel Belgium Nv | Hard capsules |
| US11319566B2 (en) | 2017-04-14 | 2022-05-03 | Capsugel Belgium Nv | Process for making pullulan |
| US11576870B2 (en) | 2017-04-14 | 2023-02-14 | Capsugel Belgium Nv | Pullulan capsules |
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2005
- 2005-01-17 CN CN 200510013106 patent/CN1680571A/zh active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101438782B (zh) * | 2008-12-31 | 2011-04-13 | 保龄宝生物股份有限公司 | 一种保湿糖浆及其制备方法 |
| US10568839B2 (en) | 2011-01-11 | 2020-02-25 | Capsugel Belgium Nv | Hard capsules |
| CN105713051A (zh) * | 2014-12-04 | 2016-06-29 | 中国科学院生态环境研究中心 | 一种制备麦芽三糖的新方法 |
| US11319566B2 (en) | 2017-04-14 | 2022-05-03 | Capsugel Belgium Nv | Process for making pullulan |
| US11576870B2 (en) | 2017-04-14 | 2023-02-14 | Capsugel Belgium Nv | Pullulan capsules |
| US11878079B2 (en) | 2017-04-14 | 2024-01-23 | Capsugel Belgium Nv | Pullulan capsules |
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