ArticleThe Journal of organic chemistry2014
Synthesis of a poly-hydroxypyrolidine-based inhibitor of Mycobacterium tuberculosis GlgE.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 29 citations in OpenAlex.
- Structure based discovery of VMP-7 as a promising GlgE targeting lead againstFrontiers in microbiology · 2026Article
- Carbohydrate-Based Chiral Ligands for the Enantioselective Addition of Diethylzinc to Aldehydes.Pharmaceuticals (Basel, Switzerland) · 2025Article
- Multigram-Scale Synthesis of 2,5-Dideoxy-2,5-imino-d-mannitol (DMDP) and 2,5-Dideoxy-2,5-imino-d-glucitol (DGDP) from d-Fructose and l-Sorbose Using a Regioselective Appel Reaction.The Journal of organic chemistry · 2025Article
- Direct Synthesis of Glycosyl Chlorides from Thioglycosides.The Journal of organic chemistry · 2024Article
- Activation of thioglycosides under mild alkylation conditions.Carbohydrate research · 2023Article
- Activation of Thioglycosides with Copper(II) Bromide.Molecules (Basel, Switzerland) · 2022Article
- Synthesis of CFrontiers in chemistry · 2022Article
- Stereoselective synthesis of a 4-⍺-glucoside of valienamine and its X-ray structure in complex with Streptomyces coelicolor GlgE1-V279S.Scientific reports · 2021Article
- Palladium(II)-assisted activation of thioglycosides.Organic & biomolecular chemistry · 2021Article
- Synthesis of Oligosaccharide Components of the Outer Core Domain of P. aeruginosa Lipopolysaccharide Using a Multifunctional Hydroquinone-Derived Reducing-End Capping Group.Organic letters · 2018Article
- Zwitterionic pyrrolidene-phosphonates: inhibitors of the glycoside hydrolase-like phosphorylase Streptomyces coelicolor GlgEI-V279S.Organic & biomolecular chemistry · 2017Article
- Ligand-bound Structures and Site-directed Mutagenesis Identify the Acceptor and Secondary Binding Sites of Streptomyces coelicolor Maltosyltransferase GlgE.The Journal of biological chemistry · 2016Article
- Structure of Mycobacterium thermoresistibile GlgE defines novel conformational states that contribute to the catalytic mechanism.Scientific reports · 2015Article
- Crystal structures of Mycobacterium tuberculosis GlgE and complexes with non-covalent inhibitors.Scientific reports · 2015Article
- Synthesis of 2-deoxy-2,2-difluoro-α-maltosyl fluoride and its X-ray structure in complex with Streptomyces coelicolor GlgEI-V279S.Organic & biomolecular chemistry · 2015Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Long treatment times, poor drug compliance, and natural selection during treatment of Mycobacterium tuberculosis (Mtb) have given rise to extensively drug-resistant tuberculosis (XDR-TB). As a result, there is a need to identify new antituberculosis drug targets. Mtb GlgE is a maltosyl transferase involved in α-glucan biosynthesis. Mutation of GlgE in Mtb increases the concentration of maltose-1-phosphate (M1P), one substrate for GlgE, causing rapid cell death. We have designed 2,5-dideoxy-3-O-α-d-glucopyranosyl-2,5-imino-d-mannitol (9) to act as an inhibitor of GlgE. Compound 9 was synthesized using a convergent synthesis by coupling thioglycosyl donor 14 and 5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-d-fructopyranose (23) to form disaccharide 24. A reduction and intramolecular reductive amination transformed the intermediate disaccharide 24 to the desired pyrolidine 9. Compound 9 inhibited both Mtb GlgE and a variant of Streptomyces coelicolor (Sco) GlgEI with Ki = 237 ± 27 μM and Ki = 102 ± 7.52 μM, respectively. The results confirm that a Sco GlgE-V279S variant can be used as a model for Mtb GlgE. In conclusion, we designed a lead transition state inhibitor of GlgE, which will be instrumental in further elucidation of the enzymatic mechanism of Mtb GlgE.
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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.