ArticleThe Journal of organic chemistry2018
Chemoenzymatic Synthesis of Trehalosamine, an Aminoglycoside Antibiotic and Precursor to Mycobacterial Imaging Probes.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 23 citations in OpenAlex.
- Synthesis and evaluation of Trehalose-Pks13 inhibitor conjugates targeting mycobacteria.Carbohydrate research · 2025Article
- Review
- TargetingACS infectious diseases · 2024Article
- Monitoring host-pathogen interactions using chemical proteomics.RSC chemical biology · 2024Review
- AuClOrganic letters · 2022Article
- Chemical Reporters for Bacterial Glycans: Development and Applications.Chemical reviews · 2022Review
- Dismantling the bacterial glycocalyx: Chemical tools to probe, perturb, and image bacterial glycans.Bioorganic & medicinal chemistry · 2021Review
- The role of chemoenzymatic synthesis in advancing trehalose analogues as tools for combatting bacterial pathogens.Chemical communications (Cambridge, England) · 2020Article
- Anomeric Selectivity of Trehalose Transferase with Rare l-Sugars.ACS catalysis · 2020Article
- Chemoenzymatic radiosynthesis of 2-deoxy-2-[Carbohydrate research · 2019Article
Corrections and comments
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Authors and funding
9 authors at 2 institutions in 1 country.
Funding
Abstract
Trehalosamine (2-amino-2-deoxy-α,α-d-trehalose) is an aminoglycoside with antimicrobial activity against Mycobacterium tuberculosis, and it is also a versatile synthetic intermediate used to access imaging probes for mycobacteria. To overcome inefficient chemical synthesis approaches, we report a two-step chemoenzymatic synthesis of trehalosamine that features trehalose synthase (TreT)-catalyzed glycosylation as the key transformation. Soluble and recyclable immobilized forms of TreT were successfully employed. We demonstrate that chemoenzymatically synthesized trehalosamine can be elaborated to two complementary imaging probes, which label mycobacteria via distinct pathways.
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Registered trials
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