To synthesize octyl β-d-glucopyranoside (OG) and decyl β-d-glucopyranoside (DG) in three non-aqueous reaction systems, namely organic solvents, ionic liquids and co-solvent mixtures, via reverse hydrolysis reactions catalyzed by the N189F dalcochinase mutant. The highest yield of OG (67 mol%) was obtained in the reaction containing 0.5 M glucose, 3 unit ml−1 enzyme in 20% (v/v) octanol and 70% (v/v) [BMIm][PF6] at 30 °C. On the other hand, the highest yield of DG (64 mol%) was obtained in the reaction containing 0.5 M glucose, 3 unit ml−1 enzyme in 20% (v/v) decanol, 20% (v/v) acetone and 50% (v/v) [BMIm][PF6] at 30 °C. The identities of OG and DG products were confirmed by HRMS and NMR. This is the first report of enzymatic synthesis of OG and DG via reverse hydrolysis reactions in ionic liquids and co-solvent mixtures. The N189F dalcochinase mutant and the non-aqueous reaction systems described here show great potential for future commercial production of long-chain alkyl glucosides.

中文翻译：

---

在有机溶剂和离子液体中改进由工程化 β-葡萄糖苷酶催化的长链烷基葡萄糖苷合成

在有机溶剂、离子液体和共溶剂混合物三种非水反应体系中，通过N189F dalcochinaase催化的逆水解反应合成辛基β-d-吡喃葡萄糖苷（OG）和癸基β-d-吡喃葡萄糖苷（DG）突变体。在含有 0.5 M 葡萄糖、20% (v/v) 辛醇和 70% (v/v) [BMIm][PF6] 中的 3 个单位 ml-1 酶的反应中获得最高的 OG 产率（67 mol%） 30℃。另一方面，在含有 0.5 M 葡萄糖、3 单位 ml-1 酶的 20% (v/v) 癸醇、20% (v/v) 丙酮和50% (v/v) [BMIm][PF6] 在 30 °C。OG 和 DG 产品的身份通过 HRMS 和 NMR 确认。这是通过离子液体和共溶剂混合物中的反向水解反应酶促合成 OG 和 DG 的第一份报告。