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Synthesis of long-chain alkyl glucosides via reverse hydrolysis reactions catalyzed by an engineered β-glucosidase.

Abstract：

: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.

journal_name

Enzyme Microb Technol

journal_title

Enzyme and microbial technology

authors

Thenchartanan P,Pitchayatanakorn P,Wattana-Amorn P,Ardá A,Svasti J,Jiménez-Barbero J,Kongsaeree PT

doi

10.1016/j.enzmictec.2020.109591

subject

Has Abstract

pub_date

2020-10-01 00:00:00

pages

109591

eissn

0141-0229

issn

1879-0909

pii

S0141-0229(20)30084-3

journal_volume

140

pub_type

杂志文章

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