ArticleNature communications2018
Revealing the mechanism for covalent inhibition of glycoside hydrolases by carbasugars at an atomic level.
Article in Nature communications, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 43 citations in OpenAlex.
- Catalyzing Carbohydrate Cleavage: Glycosidases and Their Mechanisms.Chemical reviews · 2026Review
- Licorice-derived prenylated chalcones alleviate knee osteoarthritis via multi-target modulation of PI3K-Akt, MAPK and HIF-1α signaling: an integrative UPLC-Q-TOF-MS/MS, network pharmacology and molecular dynamics study.Frontiers in bioinformatics · 2026Article
- A gram-scale synthesis of β-L-carbafucose for engineering antibody glycans.Communications chemistry · 2025Article
- From Mechanism-Based Retaining Glycosidase Inhibitors to Activity-Based Glycosidase Profiling.Journal of the American Chemical Society · 2024Review
- Activity-based metaproteomics driven discovery and enzymological characterization of potential α-galactosidases in the mouse gut microbiome.Communications chemistry · 2024Article
- A metabolic inhibitor blocks cellular fucosylation and enables production of afucosylated antibodies.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- Chemoselective Nozaki-Hiyama-Takai-Kishi and Grignard reaction: short synthesis of some carbahexopyranoses.RSC advances · 2023Article
- Article
- (Glycan Binding) Activity-Based Protein Profiling in Cells Enabled by Mass Spectrometry-Based Proteomics.Israel journal of chemistry · 2023Article
- Structural insight into the hydrolase and synthase activities of an alkaline α-galactosidase from Arabidopsis from complexes with substrate/product.Acta crystallographica. Section D, Structural biology · 2023Article
- Synergy of R-(-)carvone and cyclohexenone-based carbasugar precursors with antibiotics to enhance antibiotic potency and inhibit biofilm formation.Scientific reports · 2022Article
- Synthesis of CFrontiers in chemistry · 2022Article
- Diversity-oriented synthesis of glycomimetics.Communications chemistry · 2021Article
- Anatomy of noncovalent interactions between the nucleobases or ribose and π-containing amino acids in RNA-protein complexes.Nucleic acids research · 2021Article
- Development of an active site titration reagent for α-amylases.Chemical science · 2020Article
- Glycoside hydrolase stabilization of transition state charge: new directions for inhibitor design.Chemical science · 2020Article
- Gram-scale carbasugar synthesisRSC advances · 2019Article
Corrections and comments
- Erratum issued
Authors and funding
14 authors at 3 institutions in 3 countries.
Funding
Abstract
Mechanism-based glycoside hydrolase inhibitors are carbohydrate analogs that mimic the natural substrate's structure. Their covalent bond formation with the glycoside hydrolase makes these compounds excellent tools for chemical biology and potential drug candidates. Here we report the synthesis of cyclohexene-based α-galactopyranoside mimics and the kinetic and structural characterization of their inhibitory activity toward an α-galactosidase from Thermotoga maritima (TmGalA). By solving the structures of several enzyme-bound species during mechanism-based covalent inhibition of TmGalA, we show that the Michaelis complexes for intact inhibitor and product have half-chair (
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.