Chemoenzymatic Synthesis of Trehalose Analogues: Rapid Access to Chemical Probes for Investigating Mycobacteria

Document Type

Article

Publication Date

8-19-2014

Publication Title

ChemBioChem

Keywords

chemoenzymatic synthesis, click chemistry, glycolipids, mycobacteria, trehalose

Abstract

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."}" data-sheets-userformat="{"2":771,"3":{"1":0},"4":[null,2,16777215],"11":4,"12":0}" style="font-size: 10pt; font-family: Arial;">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.

Comments

© 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

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