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Sequence-specific Labeling of Nucleic Acids and Proteins with Methyltransferases and Cofactor Analogues

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Intercepting a Mycobacterial Biosynthetic Pathway with Covalent Labeling.

Theodore C Warner¹, Victoria M Marando¹, Omar A Santiago-Reyes¹

¹Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society

|March 24, 2025

Summary

We developed a novel probegenic strategy using the AzLac probe to label mycobacterial cell envelopes. This method allows for selective covalent labeling and tracking of mycobacteria, aiding in infection dynamics studies.

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Area of Science:

Microbiology
Chemical Biology
Biochemistry

Background:

The mycobacterial cell envelope is vital for infection and protection, but its glycan components are difficult to modify.
Existing labeling methods have limitations in probe delivery and effectiveness.

Purpose of the Study:

To develop a new, effective strategy for labeling mycobacterial cell envelopes.
To create a small molecule probe that exploits enzyme-substrate relationships for targeted modification.

Main Methods:

Synthesized an azide-substituted trans-β-lactone probe (AzLac).
Utilized a probegenic approach where enzyme activity reveals probe functionality.
Incorporated AzLac into mycobacterial cell envelope glycans using mycolyltransferases.
Investigated probe targeting using Corynebacterium glutamicum deletion strains.

Main Results:

AzLac selectively labels the inner leaflet of the mycomembrane in mycobacteria, including Mycobacterium tuberculosis.
Cmt2 was identified as a primary mycolyltransferase target for AzLac.
Demonstrated AzLac's utility in attaching DNA barcodes to mycobacteria for infection tracking.

Conclusions:

The AzLac probe offers a valuable tool for monitoring and tracking the mycobacterial cell envelope.
The probegenic strategy of masking and revealing recognition motifs has broad applicability for diverse cellular targets.