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Reactive extraction of fructose for efficient separation of sucrose-derived glucosides produced by enzymatic glycosylation
Green Chemistry ( IF 9.3 ) Pub Date : 2020-06-30 , DOI: 10.1039/d0gc01408g Andreas Kruschitz 1, 2, 3 , Bernd Nidetzky 1, 2, 3, 4, 5
Green Chemistry ( IF 9.3 ) Pub Date : 2020-06-30 , DOI: 10.1039/d0gc01408g Andreas Kruschitz 1, 2, 3 , Bernd Nidetzky 1, 2, 3, 4, 5
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The disaccharide sucrose (α-D-glucopyranosyl-1,2-β-D-fructofuranoside) is a highly efficient donor substrate for enzymatic glucosylation reactions. A large number of commercially relevant glucosides are produced via this general route. Every sucrose-based glucosylation involves co-production of D-fructose in amounts corresponding to the target glucoside. A separation technology for selective removal, and efficient recovery, of the D-fructose co-product would be highly desirable as a generic platform for downstream process development. Here, we demonstrate organoboronate-complex reactive extraction of D-fructose into an 1-octanol/hexane (4/1, v/v) solvent using methyltrioctyl ammonium chloride as phase transfer catalyst and extractant. We show separation of the D-fructose co-product (100 mM) from equimolar mixture with 2-α-D-glucosyl-glycerol, a cosmetic ingredient that is manufactured industrially from sucrose and glycerol using sucrose phosphorylase. With the main parameters of extraction, stripping and organic phase recycling identified and their effect on product/co-product yield and purity characterized, we developed a three-step extraction process with alternating extraction and stripping stages that removed the D-fructose efficiently at 50 ml operating scale. 2-α-D-glucosyl-glycerol and D-fructose were cleanly separated and obtained in excellent purity (≥90%) at a recovery of 90% and 83%, respectively. Reactive extraction appears to be faster and more selective and resource-efficient than applicable alternatives for separation, including chromatography and membrane nanofiltration. Thus, the established extraction process is promising for industrial application. It could be generically useful to separate D-fructose from glucosides.
中文翻译：
反应性提取果糖可有效分离酶促糖基化作用产生的蔗糖衍生糖苷
二糖蔗糖（α - D-吡喃葡萄糖基-1,2-β- D-果糖呋喃糖苷）是用于酶促糖基化反应的高效供体底物。通过该一般途径可生产大量与商业相关的葡糖苷。每种基于蔗糖的葡萄糖基化都涉及与目标糖苷相对应的D-果糖的联合生产。作为用于下游工艺开发的通用平台，非常需要用于选择性除去和有效回收D-果糖副产物的分离技术。在这里，我们展示了D的有机硼酸酯-络合物反应萃取使用甲基三辛基氯化铵作为相转移催化剂和萃取剂，将果糖转化为1-辛醇/己烷（4/1，v / v）溶剂。我们示出了分离d从等摩尔混合物与2-α--fructose共产物（100毫摩尔）d -glucosyl甘油中，从蔗糖工业制造和使用蔗糖磷酸甘油的化妆品成分。确定了萃取，汽提和有机相再循环的主要参数，并表征了它们对产物/副产物收率和纯度的影响，我们开发了一种三步萃取工艺，具有交替的萃取和汽提阶段，可在50℃下有效去除D-果糖。毫升操作规模。2-α- D-葡萄糖基甘油和D干净地分离出果糖，并以优异的纯度（≥90％）得到回收率分别为90％和83％的果糖。反应性萃取似乎比适用于色谱分离和膜纳米过滤的替代方法更快，更具选择性和资源效率。因此，已建立的提取方法有望用于工业应用。从糖苷中分离D-果糖可能通常是有用的。
更新日期：2020-08-04
中文翻译：
反应性提取果糖可有效分离酶促糖基化作用产生的蔗糖衍生糖苷
二糖蔗糖（α - D-吡喃葡萄糖基-1,2-β- D-果糖呋喃糖苷）是用于酶促糖基化反应的高效供体底物。通过该一般途径可生产大量与商业相关的葡糖苷。每种基于蔗糖的葡萄糖基化都涉及与目标糖苷相对应的D-果糖的联合生产。作为用于下游工艺开发的通用平台，非常需要用于选择性除去和有效回收D-果糖副产物的分离技术。在这里，我们展示了D的有机硼酸酯-络合物反应萃取使用甲基三辛基氯化铵作为相转移催化剂和萃取剂，将果糖转化为1-辛醇/己烷（4/1，v / v）溶剂。我们示出了分离d从等摩尔混合物与2-α--fructose共产物（100毫摩尔）d -glucosyl甘油中，从蔗糖工业制造和使用蔗糖磷酸甘油的化妆品成分。确定了萃取，汽提和有机相再循环的主要参数，并表征了它们对产物/副产物收率和纯度的影响，我们开发了一种三步萃取工艺，具有交替的萃取和汽提阶段，可在50℃下有效去除D-果糖。毫升操作规模。2-α- D-葡萄糖基甘油和D干净地分离出果糖，并以优异的纯度（≥90％）得到回收率分别为90％和83％的果糖。反应性萃取似乎比适用于色谱分离和膜纳米过滤的替代方法更快，更具选择性和资源效率。因此，已建立的提取方法有望用于工业应用。从糖苷中分离D-果糖可能通常是有用的。
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