title: Chemoenzymatic synthesis of trehalose analogues: rapid access to chemical probes for investigating mycobacteria.
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.
authors.affiliation: Department of Chemistry, Central Michigan University, Mount Pleasant, MI 48859 (USA).
authors.forename: Bailey L
authors.initials: BL
authors.lastname: Urbanek
authors.forename: Douglas C
authors.initials: DC
authors.lastname: Wing
authors.forename: Krystal S
authors.initials: KS
authors.lastname: Haislop
authors.forename: Chelsey J
authors.initials: CJ
authors.lastname: Hamel
authors.forename: Rainer
authors.initials: R
authors.lastname: Kalscheuer
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Woodruff
authors.forename: Benjamin M
authors.initials: BM
authors.lastname: Swarts
mesh_terms: D057930:Click Chemistry; D005964:Glucosyltransferases / Q000378:metabolism*; D006801:Humans; D008856:Microscopy, Fluorescence; D009161:Mycobacterium / Q000166:cytology* / Q000378:metabolism*; D009164:Mycobacterium Infections / Q000382:microbiology*; D020102:Mycobacterium smegmatis / Q000166:cytology / Q000378:metabolism; D009169:Mycobacterium tuberculosis / Q000166:cytology / Q000378:metabolism; D041542:Thermoproteus / Q000201:enzymology*; D014199:Trehalose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism*
chemical_list: D014199:Trehalose; D005964:Glucosyltransferases; C099692:trehalose synthase
keywords: chemoenzymatic synthesis; click chemistry; glycolipids; mycobacteria; trehalose