Carbohydrate-active enzyme-catalyzed stereoselective glycosylation of complex natural product glycosides

IF 3.4 3区生物学 Q2 BIOTECHNOLOGY & APPLIED MICROBIOLOGY

Enzyme and Microbial Technology Pub Date : 2025-01-22 DOI:10.1016/j.enzmictec.2025.110589

Daijing Wei , Jiawei Hu , Xudong Wu , Yi Li , Wenlin Wu , Ying Xu , Xuefei Wang , Yinggang Luo

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引用次数: 0

Abstract

Natural products and their derivatives are precious resources with extensive applications in various industrial fields. Enzymatic glycosylation is an efficient approach for chemical structure diversification and biological activity alternation of natural products. Herein, we reported a stereoselective glycosylation of complex natural product glycosides catalyzed by two carbohydrate-active enzymes (CAZys). ASP OleD, a mutant of glycosyltransferase OleD from Streptomyces antibioticus, catalyzed an explicit β-1,x-linkage glycosylation of the OH group of the glycosyl moiety of the representative plant-derived complex natural product glycosides, protodioscin (1) and epimedin C (2), producing two complex glycoside derivatives. The glycoside hydrolase Δ27ThCGT, a truncated cyclodextrin glucanotransferase from Thermoanaerobacter sp., exhibited a definite α-1,x-linkage glycosylation of the OH group of the glycosyl moiety of the glycosides 1, 2, and astragaloside IV (3), generating four complex glycoside derivatives. The chemical structures and absolute configurations of these enzymatic glycosylation products were determined by analysis of their HRMS and NMR data. The present study expands the enzymatic glycosylation diversification of complex glycosides catalyzed by the CAZys.

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来源期刊

Enzyme and Microbial Technology 生物-生物工程与应用微生物

CiteScore

7.60

自引率

5.90%

发文量

142

审稿时长

38 days

期刊介绍： Enzyme and Microbial Technology is an international, peer-reviewed journal publishing original research and reviews, of biotechnological significance and novelty, on basic and applied aspects of the science and technology of processes involving the use of enzymes, micro-organisms, animal cells and plant cells. We especially encourage submissions on: Biocatalysis and the use of Directed Evolution in Synthetic Biology and Biotechnology Biotechnological Production of New Bioactive Molecules, Biomaterials, Biopharmaceuticals, and Biofuels New Imaging Techniques and Biosensors, especially as applicable to Healthcare and Systems Biology New Biotechnological Approaches in Genomics, Proteomics and Metabolomics Metabolic Engineering, Biomolecular Engineering and Nanobiotechnology Manuscripts which report isolation, purification, immobilization or utilization of organisms or enzymes which are already well-described in the literature are not suitable for publication in EMT, unless their primary purpose is to report significant new findings or approaches which are of broad biotechnological importance. Similarly, manuscripts which report optimization studies on well-established processes are inappropriate. EMT does not accept papers dealing with mathematical modeling unless they report significant, new experimental data.