ArticleJournal of visualized experiments : JoVE2017
Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues.
Article in Journal of visualized experiments : JoVE, 2017. 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, 12 citations in OpenAlex.
- TargetingACS infectious diseases · 2024Article
- Article
- Chemical Reporters for Bacterial Glycans: Development and Applications.Chemical reviews · 2022Review
- The role of chemoenzymatic synthesis in advancing trehalose analogues as tools for combatting bacterial pathogens.Chemical communications (Cambridge, England) · 2020Article
- Degradation-resistant trehalose analogues block utilization of trehalose by hypervirulent Clostridioides difficile.Chemical communications (Cambridge, England) · 2019Article
- Artificial Fusion of mCherry Enhances Trehalose Transferase Solubility and Stability.Applied and environmental microbiology · 2019Article
- Chemoenzymatic radiosynthesis of 2-deoxy-2-[Carbohydrate research · 2019Article
- Hepatocyte ALOXE3 is induced during adaptive fasting and enhances insulin sensitivity by activating hepatic PPARγ.JCI insight · 2018Article
- Chemoenzymatic Synthesis of Trehalosamine, an Aminoglycoside Antibiotic and Precursor to Mycobacterial Imaging Probes.The Journal of organic chemistry · 2018Article
- Tailoring Trehalose for Biomedical and Biotechnological Applications.Pure and applied chemistry. Chimie pure et appliquee · 2017Article
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Authors and funding
7 authors at 2 institutions in 1 country.
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Abstract
Chemically modified versions of trehalose, or trehalose analogues, have applications in biology, biotechnology, and pharmaceutical science, among other fields. For instance, trehalose analogues bearing detectable tags have been used to detect Mycobacterium tuberculosis and may have applications as tuberculosis diagnostic imaging agents. Hydrolytically stable versions of trehalose are also being pursued due to their potential for use as non-caloric sweeteners and bioprotective agents. Despite the appeal of this class of compounds for various applications, their potential remains unfulfilled due to the lack of a robust route for their production. Here, we report a detailed protocol for the rapid and efficient one-step biocatalytic synthesis of trehalose analogues that bypasses the problems associated with chemical synthesis. By utilizing the thermostable trehalose synthase (TreT) enzyme from Thermoproteus tenax, trehalose analogues can be generated in a single step from glucose analogues and uridine diphosphate glucose in high yield (up to quantitative conversion) in 15-60 min. A simple and rapid non-chromatographic purification protocol, which consists of spin dialysis and ion exchange, can deliver many trehalose analogues of known concentration in aqueous solution in as little as 45 min. In cases where unreacted glucose analogue still remains, chromatographic purification of the trehalose analogue product can be performed. Overall, this method provides a "green" biocatalytic platform for the expedited synthesis and purification of trehalose analogues that is efficient and accessible to non-chemists. To exemplify the applicability of this method, we describe a protocol for the synthesis, all-aqueous purification, and administration of a trehalose-based click chemistry probe to mycobacteria, all of which took less than 1 hour and enabled fluorescence detection of mycobacteria. In the future, we envision that, among other applications, this protocol may be applied to the rapid synthesis of trehalose-based probes for tuberculosis diagnostics. For instance, short-lived radionuclide-modified trehalose analogues (e.g.,
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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.