Fig. 1 (a) Structure and biosynthesis of mycolate-containing components of the mycomembrane, including
TDM, AGM, and O-mycoloylated proteins. (b) Schemes for metabolic labeling of live mycobacteria with
trehalose-based probes via one- and two-step approaches. AG arabinogalactan, MM mycomembrane, PG
peptidoglycan, PM plasma membrane, X bioorthogonal functional group being metabolically incorporated into
the bacterium, Y complementary bioorthogonal functional group undergoing selective reaction with X, green
star functionality being delivered to the bacterium (e.g., fluorophore, affinity tag, photoactivatable group,
diagnostic or therapeutic cargo)
Fig. 2 Examples of synthetic (a) trehalose-mimicking and (b) TMM-mimicking probes for metabolic labeling of
mycobacteria and comments on their labeling characteristics. Presently, 6-TreAz and O-AlkTMM-C7 are
commercially available. The remaining probes can be synthesized according to the references given for each
Trehalose Probe Labeling
387
TDM, AGM, and O-mycoloylated proteins. (b) Schemes for metabolic labeling of live mycobacteria with
trehalose-based probes via one- and two-step approaches. AG arabinogalactan, MM mycomembrane, PG
peptidoglycan, PM plasma membrane, X bioorthogonal functional group being metabolically incorporated into
the bacterium, Y complementary bioorthogonal functional group undergoing selective reaction with X, green
star functionality being delivered to the bacterium (e.g., fluorophore, affinity tag, photoactivatable group,
diagnostic or therapeutic cargo)
Fig. 2 Examples of synthetic (a) trehalose-mimicking and (b) TMM-mimicking probes for metabolic labeling of
mycobacteria and comments on their labeling characteristics. Presently, 6-TreAz and O-AlkTMM-C7 are
commercially available. The remaining probes can be synthesized according to the references given for each
Trehalose Probe Labeling
387