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Assessing biocatalysis using dihydrolevoglucosenone (Cyrene™) as versatile bio-based (co)solvent
Molecular Catalysis ( IF 3.9 ) Pub Date : 2020-02-13 , DOI: 10.1016/j.mcat.2020.110813
Nadia Guajardo , Pablo Domínguez de María

An emerging biogenic aprotic solvent is the cellulose-derived dihydrolevoglucosenone, or 6,8-dioxabicyclooctanone (Cyrene™). This paper explores the use of Cyrene in lipase-catalyzed biotransformations, both in aqueous solutions – as co-solvent – as well as non-conventional media for synthesis. Cyrene is useful as organic solvent for lipophilizations using benzoic acid and glycerol as a model system for substrates with unpaired solubilities. The immobilized lipase B from Candida antarctica is active in Cyrene, yielding up to ∼ 10 g product L−1. Interestingly, crosslinked aggregates immobilized lipases (CLEA) remain significantly stable in Cyrene, enabling its use along several catalytic cycles. Cyrene is highly hygroscopic and forms geminal-diol structures with water, leading to solvent mixtures with a (tailored) gradient of polarities, what may be promising for biocatalysis in aqueous solutions. CALB displays hydrolytic reactions with different proportions of Cyrene as cosolvent, and CLEA derivatives remain fully active over 6 cycles at 30 % v/v Cyrene.



中文翻译:

使用二氢左旋葡糖醛酮(Cyrene™)作为通用的生物基(共)溶剂评估生物催化

一种新兴的生物非质子溶剂是纤维素衍生的二氢左旋葡糖醛酮,或6,8-二氧杂双环辛酮(Cyrene™)。本文探讨了C在脂肪酶催化的生物转化中的用途,包括水溶液(作为助溶剂)以及非常规合成介质。yr可用作使用苯甲酸和甘油作为不配对溶解度的底物的模型系统进行脂化的有机溶剂。来自南极假丝酵母的固定化脂肪酶B在Cyrene中具有活性,最多可产生约10 g的产物L -1。有趣的是,固定化交联的脂肪酶的交联聚集体(CLEA)在C中保持显着稳定,从而使其可以在多个催化循环中使用。yr具有高度吸湿性,可与水形成双晶二醇结构,从而导致溶剂混合物的极性梯度(量身定做),有望在水溶液中进行生物催化。CALB显示出不同比例的C作为助溶剂的水解反应,CLEA衍生物在30%v / v的C下经过6个循环仍保持完全活性。

更新日期:2020-02-20
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