Synthesis of Long-Chain Alkyl Glucosides via Reverse Hydrolysis Reactions Catalyzed by an Engineered β-Glucosidase,Enzyme and Microbial Technology

当前位置： X-MOL 学术 › Enzyme Microb. Technol. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Synthesis of Long-Chain Alkyl Glucosides via Reverse Hydrolysis Reactions Catalyzed by an Engineered β-Glucosidase
Enzyme and Microbial Technology ( IF 3.4 ) Pub Date : 2020-10-01 , DOI: 10.1016/j.enzmictec.2020.109591
Pornpanna Thenchartanan ₁ , Phiraya Pitchayatanakorn ₁ , Pakorn Wattana-Amorn ₂ , Ana Ardá ₃ , Jisnuson Svasti ₄ , Jesús Jiménez-Barbero ₅ , Prachumporn T Kongsaeree ₁

Affiliation

Long-chain alkyl glucosides, such as octyl and decyl β-d-glucopyranosides (OG and DG, respectively), are regarded as a new generation of biodegradable, non-ionic surfactants. Previously, the mutants of Dalbergia cochinchinensis Pierre dalcochinase showed potential in the synthesis of oligosaccharides and alkyl glucosides. In this study, the N189F dalcochinase mutant gave the highest yields of OG and DG synthesis under reverse hydrolysis conditions. The optimized yield of OG (57.5 mol%) was obtained in the reactions containing 0.25 M glucose and 0.3 units of the N189 F mutant in buffer-saturated octanol at 30 °C. The identity of OG and DG products was confirmed by high resolution mass spectrometry (HRMS) and NMR. Consistent with its capability for synthesis, the reactivation kinetics and ITC analysis revealed that the aglycone binding pocket of the N189F mutant was more favorable for long-chain alkyl alcohols than the wild-type dalcochinase, while their glycone binding pockets showed similar affinity for the glucosyl moiety. STD NMR revealed higher interactions at the aglycone sites than the glycone sites. Our results demonstrated a promising potential of the N189F dalcochinase mutant in the future commercial production of long-chain alkyl glucosides via reverse hydrolysis reactions.

更新日期：2020-10-01

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南

全部期刊列表>>