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Exploiting thioether reactivity to label mycobacterial glycans.

Stephanie R Smelyansky^1,2, Chi-Wang Ma^1,2, Victoria M Marando¹

¹Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139.

Proceedings of the National Academy of Sciences of the United States of America

|May 5, 2025

Summary

Researchers developed a new method to label Mycobacterium tuberculosis (Mtb) cell envelope glycans using a unique sugar called methylthioxylofuranose (MTX). This allows visualization of ManLAM in live cells, aiding the study of Mtb infection.

Keywords:

Mycobacterium tuberculosis bioconjugation glycans mannose-capped lipoarabinomannan mycobacteria

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Mass Spectrometric Analysis of Glycosphingolipid Antigens

Mass Spectrometric Analysis of Glycosphingolipid Antigens

Published on: April 16, 2013

Area of Science:

Microbiology
Glycobiology
Chemical Biology

Background:

Mycobacterium tuberculosis (Mtb) poses a significant global health threat, with its cell envelope glycans acting as crucial virulence factors.
Studying Mtb glycans is challenging due to the lack of methods for site-selective modification and labeling.
Mannose-capped lipoarabinomannan (ManLAM) is a key Mtb glycolipid involved in immune evasion.

Purpose of the Study:

To develop a novel bioconjugation strategy for site-selective labeling of Mtb glycans.
To exploit the unique thioether in methylthioxylofuranose (MTX) for selective glycan modification.
To visualize ManLAM localization and dynamics during infection.

Main Methods:

Utilized an oxaziridine probe to target the thioether in MTX-containing glycans.
Performed selective labeling of MTX-glycans in vitro and in live Mtb cells.
Visualized ManLAM localization in live cells and a macrophage infection model.

Main Results:

Demonstrated selective labeling of MTX-glycans, even in the presence of protein methionine.
Successfully visualized ManLAM localization in live cells and during macrophage infection.
Showcased the stability of the label and Mtb cell envelope in an infection model.

Conclusions:

Developed a novel and efficient method for site-selective glycan labeling in Mtb.
The MTX thioether serves as a valuable handle for glycan bioconjugation.
This approach enables dynamic studies of Mtb cell envelope components during infection.