Reactive extraction of fructose for efficient separation of sucrose-derived glucosides produced by enzymatic glycosylation

We provide here the underlying data of the scientific publication "Reactive extraction of fructose for efficient separation of sucrose-derived glucosides produced by enzymatic glycosylation". Please find the abstract below: 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本数据集配套于科学出版物《酶法糖基化制备蔗糖衍生糖苷的果糖反应萃取高效分离》（原文标题：Reactive extraction of fructose for efficient separation of sucrose-derived glucosides produced by enzymatic glycosylation），其摘要如下：二糖蔗糖（α-D-吡喃葡萄糖基-1,2-β-D-呋喃果糖苷）是酶法糖基化反应的高效供体底物。目前诸多具备商业应用价值的糖苷均通过该通用工艺路线制备。每一轮以蔗糖为底物的糖基化反应，都会联产与目标糖苷物质的量相等的D-果糖。开发可选择性脱除并高效回收该D-果糖副产物的分离技术，将成为下游工艺开发的理想通用平台。本研究采用三辛基甲基氯化铵（methyltrioctyl ammonium chloride）作为相转移催化剂（phase transfer catalyst）与萃取剂（extractant），利用有机硼络合物反应萃取法将D-果糖萃取至1-辛醇/己烷（4/1，体积比）的混合溶剂体系中。我们成功实现了从与化妆品原料2-α-D-葡萄糖基甘油（2-α-D-glucosyl-glycerol）的等摩尔混合物中分离100 mM的D-果糖副产物；该化妆品原料可通过蔗糖磷酸化酶（sucrose phosphorylase）催化蔗糖与甘油的反应实现工业规模化生产。在明确萃取、反萃取（stripping）及有机相循环（organic phase recycling）的核心工艺参数，并表征其对产物/副产物收率与纯度的影响后，我们开发了一套交替进行萃取与反萃阶段的三步萃取工艺，可在50 mL的操作规模下高效脱除D-果糖。2-α-D-葡萄糖基甘油与D-果糖实现了完全分离，二者的回收率分别为90%与83%，纯度均≥90%。相较于色谱法（chromatography）、膜纳滤（membrane nanofiltration）等现有可行的替代分离技术，反应萃取法展现出更快的反应速率、更高的选择性与资源利用效率。因此，本研究建立的萃取工艺具备良好的工业应用前景，可广泛用于从糖苷混合物中分离D-果糖。