Chemoenzymatic Synthesis of Trehalose Analogues: Rapid Access to Chemical Probes for Investigating Mycobacteria |
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| Authors: | Bailey L. Urbanek Douglas C. Wing Krystal S. Haislop Chelsey J. Hamel Dr. Rainer Kalscheuer Prof. Peter J. Woodruff Prof. Benjamin M. Swarts |
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| Affiliation: | 1. Department of Chemistry, Central Michigan University, Mount Pleasant, MI 48859 (USA);2. Department of Chemistry, University of Southern Maine, Portland, ME 04104 (USA);3. Institute for Medical Microbiology and Hospital Hygiene, Heinrich‐Heine‐University Duesseldorf, 40225 Duesseldorf (Germany) |
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| Abstract: | Trehalose analogues are emerging as valuable tools for investigating Mycobacterium tuberculosis, but progress in this area is slow due to the difficulty in synthesizing these compounds. Here, we report a chemoenzymatic synthesis of trehalose analogues that employs the heat‐stable enzyme trehalose synthase (TreT) from the hyperthermophile Thermoproteus tenax. By using TreT, various trehalose analogues were prepared quickly (1 h) in high yield (up to >99 % by HPLC) in a single step from readily available glucose analogues. To demonstrate the utility of this method in mycobacteria research, we performed a simple “one‐pot metabolic labeling” experiment that accomplished probe synthesis, metabolic labeling, and imaging of M. smegmatis in a single day with only TreT and commercially available materials. |
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| Keywords: | chemoenzymatic synthesis click chemistry glycolipids mycobacteria trehalose |
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