CN100379872C - 具有延长链和低血糖指数的异麦芽糖寡糖的制备方法 - Google Patents
具有延长链和低血糖指数的异麦芽糖寡糖的制备方法 Download PDFInfo
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Abstract
本发明涉及延长链长的异麦芽糖寡糖的制备方法。在glucansucrase存在下将异麦芽糖寡糖直接转化成延长链长的异麦芽糖寡糖。所述产品可以运用于食品、饲料、饮料、化妆品或药品中，尤其是用作缓慢消化或不易消化的寡糖、低热供给者、益生元、矿物质吸收促进剂、非龋齿药剂和/或低血糖指数调节糖浆。
Description
技术领域
本发明涉及具有延长的链长和低血糖指数的异麦芽糖寡糖的制备方法。
发明背景
异麦芽糖寡糖如异麦芽三糖和异麦芽四糖作为促进双歧杆菌(bifid bacteria)生长的糖是已知的，且它们在大肠中刺激认为对个体健康有益的细菌的生长。尤其是，已知双歧杆菌属(Bifidobacteria)对一般健康状况具有正面影响。
进一步描述了将富含异麦芽糖(二糖)的糖浆转化成含有异麦芽三糖和异麦芽四糖的糖浆时，提高的双歧杆菌刺激效果(即，口服每重量单位异麦芽糖寡糖增加的双歧杆菌数量)。
因此最有效的双歧杆菌刺激异麦芽糖寡糖糖浆由高含量的较长链支链寡糖如异麦芽三糖、异麦芽四糖、异麦芽五糖、异麦芽六糖和更高类似物组成。
US4,649,058涉及延长链葡萄糖寡糖的制备方法，通过将单糖或二糖作为受体在α-葡糖基转移酶存在下和蔗糖反应。
迄今，现有方法通常从低分子量的纯受体开始，所述受体至多为二糖。
因此需要可以使用混合物的方法，其中受体不受限于其分子量。本发明人提供了这样的方法。
发明概述
本发明涉及延长异麦芽糖寡糖链长的方法，特征在于所述方法包括存在于糖类糖浆中的蔗糖和异麦芽糖寡糖之间的酶转移反应。该酶转移反应在葡聚糖蔗糖酶(glucansucrase)存在下进行，其中该葡聚糖蔗糖酶优选选自右旋糖酐蔗糖酶(dextransucrase)、alternansucrase、齿斑葡聚糖蔗糖酶(mutansucrase)及其混合物。
本发明进一步涉及包括以下步骤的方法：
a)使用一种或多种生产异麦芽糖寡糖的酶将麦芽糖寡糖糖浆转化成含有异麦芽糖寡糖的糖类糖浆，
b)将蔗糖加入含有异麦芽糖寡糖的糖类糖浆中，
c)加入glucansucrase，
d)将糖类糖浆中的异麦芽糖寡糖转化成延长链的异麦芽糖寡糖，用于获得糖浆混合物。
尤其是，本发明涉及其中生产异麦芽糖寡糖的酶是转葡糖苷酶的方法。
优选，本发明涉及方法，其中步骤a)和b)之间，将含有异麦芽糖寡糖的糖类糖浆通过色谱纯化，以便从中除去葡萄糖。
本发明进一步涉及方法，包括将含有延长链长的异麦芽糖寡糖的糖浆混合物进行色谱纯化。
特定实施方案中，在可重复使用的载体上进行一种或多种生产异麦芽糖寡糖的酶存在下的工艺步骤和/或glucansucrase存在下的工艺步骤。
此外，本发明涉及通过之前所述方法可获得的含有延长链长异麦芽糖寡糖的糖浆。
此外，本发明涉及含有延长链长异麦芽糖寡糖的糖浆在食品、饮料、饲料、化妆品或药品中的用途。
其可以用作缓慢消化或不易消化的寡糖、低热供给者、益生元(prebiotic)、矿物质吸收促进剂、非龋齿药剂和/或低血糖指数调节糖浆。
详述
本发明涉及延长异麦芽糖寡糖链长的方法，特征在于所述方法包括存在于糖类糖浆中的蔗糖和异麦芽糖寡糖之间的酶转移反应。在此所用的术语“异麦芽糖寡糖”指的是含有三个或更多单糖单体的异麦芽糖寡糖。异麦芽糖寡糖的直接转移反应直接生成延长链长的异麦芽糖寡糖。
在glucansucrase存在下进行酶转移反应。glucansucrase优选选自葡聚糖蔗糖酶、alternansucrase、齿斑葡聚糖蔗糖酶及其混合物。通过使用alternansucrase或齿斑葡聚糖蔗糖酶，可以获得不同连接的寡糖。
本发明进一步涉及包括以下步骤的方法：
a)使用一种或多种生产异麦芽糖寡糖的酶将麦芽糖寡糖糖浆转化成含有异麦芽糖寡糖的糖类糖浆，
b)将蔗糖加入糖类糖浆中，
c)加入glucansucrase，
d)将糖类糖浆中的异麦芽糖寡糖转化成延长链长的异麦芽糖寡糖来生产糖浆混合物。
异麦芽糖寡糖生产酶可以选自曲霉属(Aspergillus)菌株(例如，黑曲霉(niger)、米曲霉(oryzae)、臭曲霉(foetidus)、炭黑曲霉(carbonarius)和arvamori)、短梗霉属(Aureobasidium)菌株(例如，出芽短梗霉(Pullulans))、念珠菌属(Moniella)菌株、酒香酵母属(Brettanomyces)菌株、德巴利酵母属(Debaryomyces)菌株、曲霉属(Aspergillus)菌株、根霉属(Rhizopus)菌株、酵母属(Saccharomyces)菌株、明串珠菌属(Leuconostoc)菌株和链球菌属(Streptococcus)菌株。实际上，可以使用可将麦芽糖寡糖转化成异麦芽糖寡糖的任何葡糖基转移酶或α-葡糖苷酶。
尤其是，本发明涉及其中生产异麦芽糖寡糖的酶是转葡糖苷酶的方法，其中步骤a)可以和描述于EP 0875585中的酶反应相似。
第一步中，该方法包括使用作用于麦芽糖寡糖糖浆(即，含有麦芽糖和/或麦芽三糖的糖浆)的转葡糖苷酶来生产异麦芽糖寡糖。在转葡糖苷酶存在下从麦芽糖糖浆合成异麦芽糖寡糖的过程中，产生了相当大量(总糖类重量的15-40％)的葡萄糖。当获得所需组成的异麦芽糖寡糖时，将蔗糖和葡聚糖蔗糖酶加入糖类糖浆中来生产较长的异麦芽糖寡糖分子(从存在于糖类糖浆中的异麦芽糖寡糖开始)。
由于蔗糖不是转葡糖苷酶的底物，只有葡聚糖蔗糖酶利用蔗糖来延长异麦芽糖寡糖。
为了纯化异麦芽糖寡糖和除去转移反应过程中形成的相当量的葡萄糖，可以在该方法的步骤a)和b)之间使用色谱。
本发明进一步涉及方法，包括将含有延长链长异麦芽糖寡糖的糖浆混合物用色谱纯化。
特定实施方案中，在可重复使用的载体上进行一种或多种生产异麦芽糖寡糖的酶存在下的工艺步骤和/或葡聚糖蔗糖酶存在下的工艺步骤。实际上，通过使用固定化形式的一种或多种异麦芽糖寡糖生产酶和/或glucansucrase可以进一步提高工业实用性。酶可以是固定化形式的如交联酶晶体。酶可以固定于载体上，更优选固定于可重复使用的载体上。
对于该目的，可重复使用意思是载体可以以一定方式被除去酶或酶活性，而载体材料保持完整。载体可以连续或间隔再生。载体材料可以重复装载酶和重复使用。例如，可以用酸或碱溶液洗涤来进行载体的清洗。可以分批或在柱上完成该清洗。加入盐是有利的。另一可能性是使用蛋白降解酶。另一方法是将材料加热。
优选，载体是惰性的，理解为不会影响底物转化成转化产物。此外，优选描述成多孔和基本上不可压缩的载体。术语“多孔”指的是固体载体含有提供大的表面积的多个洞和孔。采用多孔材料的实例是磁稳定的流化床酶反应器。术语“基本上不可压缩的”意思是固体载体在转化过程中可能经常用到的压力下不会变形至任何明显的程度。
优选，所用的材料具有阴离子交换基团。这样的材料可以基于纤维素。其它更优选的载体是基于聚丙烯酸酯或聚苯乙烯的具有弱碱性基团的载体。弱碱性阴离子交换剂是具有伯和/或仲或叔氨基的材料。它们在酸性溶液中解离并具有交换能力。具有叔氨基的材料具有相当的碱性，还将其称为中等碱性的阴离子交换剂。优选，使用基于酚醛树脂的载体，如可购得的DuoliteTMA568(Rohm和Hass)。
优选，载体是阴离子交换树脂并通过吸附即非共价方式将酶固定于其上。这使得易于除去失活的酶并随后再装载新鲜的酶。载体的再装载导致偶联物活性的完全恢复。这意味着在其被替换之前载体材料可以使用相当长的时间。还有，用交联剂处理，如戊二醛可以稳定固定化酶。
此外，本发明涉及通过之前所述方法可获得的含有延长链长的异麦芽糖寡糖的糖浆。
此外，本发明涉及含有延长链长的异麦芽糖寡糖的糖浆在食品、饮料、饲料、化妆品或药品中的用途。
其可以用作缓慢消化或不易消化的寡糖、低热供给者、益生元、矿物质吸收促进剂、非龋齿药剂和/或低血糖指数调节糖浆。
将含有延长链长的异麦芽糖寡糖的特定糖浆定义为糖类原料，和麦芽糖相比较，其提供了较慢的释放并因此在通过小肠传送的过程中较慢地将葡萄糖吸收入体内。
所述特定糖浆的运用是多倍，即，它们可以用于将足够的碳水化合物传送至糖尿病患者而血清葡萄糖水平无显著升高。此外，将特定糖浆加入葡萄糖耐受力降低的老年人的膳食中具有有益效果。
在运动营养方面，所述特定糖浆具有令人感兴趣的运用。所述糖浆可以给运动员提供身体训练过程中的稳定和恒定的碳水化合物供给。有利的，因此糖浆可以用作运动或能量饮料的成分。
本发明还提供了所述糖浆在食品或饮用组合物(＝饮料)中的用途。通常，食品组合物可以是糖尿病食品、婴儿食品、规定食物，例如用于坐着不动的人群，或用于葡萄糖耐受力降低人群例如老年人的特定配制食品。
所述糖浆在食品和饮料组合物中的存在提供了之前所述的较慢释放，并因此较慢地将葡萄糖吸收入体内。这和低血糖指数相关。
本发明具有以下优势：
-通过简单方法可以制得延长链长的异麦芽糖寡糖，
-不需要使用纯的受体来生产延长链长的异麦芽糖寡糖，
-异麦芽糖寡糖直接反应来获得延长链长的异麦芽糖寡糖，
-通过本方法可荻得的产物显示出数个健康有益效果，其在食品、饮料、饲料、化妆品和药品中是有用的。
通过以下实施例来说明本发明.
实施例1
将糖浆(IMO，组成：20.4％DP1，26.0％DP2，31.2％DP3，11.7％DP4，3.9％DP5，1.6％DP6，0.8％DP7，0.5％DP8，0.3％DP9，0.2％DP10，3.4％DP＞10，根据EP 0 875 585 的方法可获得)浓缩至33％w/w，以80/20至50/50(v/v)范围内的不同比例加入33％w/w蔗糖溶液。使用0.1N HC l将溶液的pH调节至5.2。所有溶液在30℃温热20分钟，将2ml活性3.7U/ml的葡聚糖蔗糖酶溶液加至20ml制得的异麦芽糖寡糖/蔗糖溶液中。
将溶液在30℃培育，然后在培育48小时后取样。用3ml软化水稀释样品并放入沸水浴中10分钟。使用0.45μm滤器过滤溶液并通过HPLC分析。获得的结果显示于表1中。
表1：最终组成以％表示(HPLC结果)
当底物具有高浓度DP2-DP3时，反应48小时后，在DP4-DP5范围(＝延长链长的异麦芽糖寡糖)观察到高浓度。
实施例2
将糖浆(IMO，组成：20.4％DP1，26.0％DP2，31.2％DP3，11.7％DP4，3.9％DP5，1.6％DP6，0.8％DP7，0.5％DP8，0.3％DP9，0.2％DP10，3.4％DP＞10，根据EP0875585的方法可获得)浓缩至33％(w/w)，以80/20至50/50(v/v)范围内的不同比例加入33％蔗糖溶液(w/w)。使用0.1N HCl将溶液的pH调节至5.2。所有溶液在30℃温热20分钟，并加入2ml活性6.6U/ml的alternansucrase溶液(Leuconostocmesenteroides NRRL B-1355)。
将溶液在30℃培育，然后在培育48小时后取样。用3ml软化水稀释样品并放入沸水浴中10分钟。使用0.45μm滤器过滤溶液并通过HPLC分析。获得的结果显示于表2中。
表2：最终组成以％表示(HPLC结果)
当底物具有高浓度DP2-DP3时，反应48小时后，在DP4-DP6范围(＝延长链长的异麦芽糖寡糖)观察到高浓度。
体外消化实施例2中制得的糖浆
将IMO糖浆(组成：20.4％DP1，26.0％DP2，31.2％DP3，11.7％DP4，3.9％DP5，1.6％DP6，0.8％DP7，0.5％DP8，0.3％DP9，0.2％DP10，3.4％DP＞10；根据EP 0 875 585的方法可获得)和实施例2通过50/50IMO蔗糖(v/v)溶液中葡聚糖蔗糖酶的作用获得的糖浆，用猪肠丙酮粉在37℃和pH6培育2小时。
麦芽糖作为参照。结果显示于表3中。
表3：
| 糖浆 | 和参照相比较释放的葡萄糖％ |
| 麦芽糖 | 100 |
| IMO | 26 |
| 延长的IMO(实施例2) | 15.5 |
结果清楚地证明了本发明获得的糖浆消化性慢。
Claims (15)
1.延长异麦芽糖寡糖链长的方法，特征在于所述方法包括存在于糖类糖浆中的蔗糖和异麦芽糖寡糖之间的酶转移反应，其中在葡聚糖蔗糖酶存在下进行酶转移反应。
2.根据权利要求1的方法，特征在于葡聚糖蔗糖酶选自右旋糖酐蔗糖酶、alternansucrase、齿斑葡聚糖蔗糖酶及其混合物。
3.根据权利要求1或2的方法，特征在于所述方法包括以下步骤：
a)使用一种或多种生产异麦芽糖寡糖的酶将麦芽糖寡糖糖浆转化成含有异麦芽糖寡糖的糖类糖浆，
b)将蔗糖加入所述糖类糖浆中，
c)加入葡聚糖蔗糖酶，
d)将糖类糖浆中的异麦芽糖寡糖转化成具有延长链长的异麦芽糖寡糖来生产糖浆混合物。
4.根据权利要求3的方法，特征在于步骤a)中生产异麦芽糖寡糖的酶是转葡糖苷酶。
5.根据权利要求4的方法，特征在于步骤a)和b)之间，通过色谱纯化从糖类糖浆中除去葡萄糖。
6.根据权利要求3的方法，特征在于进一步包括对步骤d)的糖浆混合物进行色谱纯化。
7.根据权利要求3的方法，特征在于在可重复使用载体上进行一种或多种生产异麦芽糖寡糖的酶存在下的工艺步骤和/或葡聚糖蔗糖酶存在下的工艺步骤。
8.根据权利要求1至7任一项获得的含有具有延长链长的异麦芽糖寡糖的糖浆。
9.根据权利要求8的糖浆在食品、饮料、饲料、化妆品或药品中的用途。
10.根据权利要求8的糖浆作为缓慢消化或不易消化寡糖的用途。
11.根据权利要求8的糖浆作为低热量供给品的用途。
12.根据权利要求8的糖浆作为益生元的用途。
13.根据权利要求8的糖浆作为矿物质吸收促进剂的用途。
14.根据权利要求8的糖浆作为非龋齿剂的用途。
15.根据权利要求8的糖浆作为低血糖指数调节糖浆的用途。
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| DE102006014543A1 (de) * | 2006-03-21 | 2007-09-27 | Südzucker AG Mannheim/Ochsenfurt | Funktionelle Lebensmittel gegen Tumore |
| US20090060943A1 (en) * | 2007-08-31 | 2009-03-05 | O'mara Brendan Joseph | Syndrome X Composition and Method of Lowering Blood Pressure and Glycemic Index |
| KR101091138B1 (ko) | 2009-03-26 | 2011-12-09 | 한국생명공학연구원 | 류코노스톡 락티스로부터 유래된 글루칸수크라제 및 그 제조방법 |
| US8617636B2 (en) | 2009-10-01 | 2013-12-31 | Roquette Freres | Carbohydrate compositions having a greater impact on the insulinemic response than on the glycemic response, their preparation and their uses |
| CN102796783B (zh) * | 2012-08-23 | 2015-02-11 | 江南大学 | 一种聚合度为3-8功能葡聚糖的生物加工方法 |
| CA2958712C (en) | 2014-09-22 | 2019-11-26 | Nihon Shokuhin Kako Co., Ltd. | Slowly digestible, sustained-type energy supplying agent |
| JP7208924B2 (ja) | 2017-05-23 | 2023-01-19 | ニュートリション・アンド・バイオサイエンシーズ・ユーエスエー・フォー，インコーポレイテッド | α－１，３－グルカンの酵素的製造 |
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| CN108384822A (zh) * | 2018-02-13 | 2018-08-10 | 江南大学 | 一种新型葡聚三糖及其多酶法制备方法 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4649058A (en) * | 1984-06-15 | 1987-03-10 | Pfeifer & Langen | Gluco-oligosaccharide mixture and a process for its manufacture |
| CN1205843A (zh) * | 1997-05-02 | 1999-01-27 | 塞里斯塔控股有限公司 | 一种富含异麦芽低聚糖糖浆的制备方法 |
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|---|---|---|---|---|
| DE3422246C1 (de) * | 1984-06-15 | 1986-03-27 | Pfeifer & Langen, 5000 Köln | Verfahren zur Herstellung monovalenter Haptene |
| JP4273277B2 (ja) * | 1999-06-30 | 2009-06-03 | 大塚製薬株式会社 | オリゴ糖補給組成物 |
| WO2002018614A1 (fr) * | 2000-08-30 | 2002-03-07 | Amano Enzyme Inc. | Methode visant a augmenter le rendement d'oligosaccharides contenant $g(a)-galactosyle et compositions anti-candida |
| CA2421201A1 (en) * | 2000-09-05 | 2002-03-14 | Lion Nathan Brands Company Limited | High soluble dietary fibre fermented beverage and process for its production |
| US7435564B2 (en) * | 2003-09-29 | 2008-10-14 | Instituto Technologico Y De Estudios Superiores De Monterrey | Production of invert syrup from sugarcane juice using immobilized invertase |
-
2003
- 2003-02-08 GB GBGB0302894.1A patent/GB0302894D0/en not_active Ceased
-
2004
- 2004-02-05 EP EP04708319A patent/EP1589831B1/en not_active Expired - Lifetime
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- 2004-02-05 CN CNB2004800035946A patent/CN100379872C/zh not_active Expired - Lifetime
- 2004-02-05 WO PCT/EP2004/001060 patent/WO2004068966A1/en active IP Right Grant
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-
2011
- 2011-06-07 JP JP2011127028A patent/JP2011167209A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4649058A (en) * | 1984-06-15 | 1987-03-10 | Pfeifer & Langen | Gluco-oligosaccharide mixture and a process for its manufacture |
| CN1205843A (zh) * | 1997-05-02 | 1999-01-27 | 塞里斯塔控股有限公司 | 一种富含异麦芽低聚糖糖浆的制备方法 |
Non-Patent Citations (1)
| Title |
|---|
| "功能性异麦芽低聚糖的开发和应用". 李光伟，汪钊.广州食品工业科技，第126卷第4期. 2000 * |
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| GB0302894D0 (en) | 2003-03-12 |
| ATE392818T1 (de) | 2008-05-15 |
| DE602004013276T2 (de) | 2008-07-24 |
| EP1589831A1 (en) | 2005-11-02 |
| DK1589831T3 (da) | 2008-08-18 |
| US20060148040A1 (en) | 2006-07-06 |
| EP1589831B1 (en) | 2008-04-23 |
| DE602004013276D1 (de) | 2008-06-05 |
| WO2004068966A1 (en) | 2004-08-19 |
| JP2011167209A (ja) | 2011-09-01 |
| JP2006518200A (ja) | 2006-08-10 |
| CN1747659A (zh) | 2006-03-15 |
| PT1589831E (pt) | 2008-05-14 |
| US7670811B2 (en) | 2010-03-02 |
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