Figure 4.

Mycobacterium Tuberculosis TreS Converts the α Anomers of Deoxyfluoromaltose Analogs

(A) The conversion of pre-equilibrated 2-deoxy-2-fluoro-α/β-maltose (10 mM) by TreS (2 μM) was monitored using ¹⁹F-NMR spectroscopy (see Figure S3A for spectra). The times taken to produce 2 mM 2-deoxy-2-fluorotrehalose and consume 50% of the maltose analog were 25 and 125 min, respectively, both ∼2-fold longer than with maltose.

(B) Corresponding data with 3-deoxy-3-fluoro-α/β-maltose (Figure S3B). The time taken to consume 50% of the maltose analog was 1,100 min, 20-fold longer than with maltose. No 3-deoxy-3-fluorotrehalose was detected.

(C) Corresponding data with 6-deoxy-6-fluoro-α/β-maltose (Figure S3C). The times taken to produce 2 mM 6-deoxy-6-fluorotrehalose and consume 50% of the maltose analog were 2,500 and 1,500 min, respectively, 180- and 27-fold longer than with maltose.

(D) Proposed reaction scheme to account for the conversion of deoxyfluoromaltoses by TreS.