Probing the Mycobacterial Trehalome with Bioorthogonal Chemistry

[Image: see text] Mycobacteria, including the pathogen Mycobacterium tuberculosis, use the non-mammalian disaccharide trehalose as a precursor for essential cell-wall glycolipids and other metabolites. Here we describe a strategy for exploiting trehalose metabolic pathways to label glycolipids in my...

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Autores principales: Swarts, Benjamin M., Holsclaw, Cynthia M., Jewett, John C., Alber, Marina, Fox, Douglas M., Siegrist, M. Sloan, Leary, Julie A., Kalscheuer, Rainer, Bertozzi, Carolyn R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2012
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3466019/
https://www.ncbi.nlm.nih.gov/pubmed/22978752
http://dx.doi.org/10.1021/ja3062419
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author Swarts, Benjamin M.
Holsclaw, Cynthia M.
Jewett, John C.
Alber, Marina
Fox, Douglas M.
Siegrist, M. Sloan
Leary, Julie A.
Kalscheuer, Rainer
Bertozzi, Carolyn R.
author_facet Swarts, Benjamin M.
Holsclaw, Cynthia M.
Jewett, John C.
Alber, Marina
Fox, Douglas M.
Siegrist, M. Sloan
Leary, Julie A.
Kalscheuer, Rainer
Bertozzi, Carolyn R.
author_sort Swarts, Benjamin M.
collection PubMed
description [Image: see text] Mycobacteria, including the pathogen Mycobacterium tuberculosis, use the non-mammalian disaccharide trehalose as a precursor for essential cell-wall glycolipids and other metabolites. Here we describe a strategy for exploiting trehalose metabolic pathways to label glycolipids in mycobacteria with azide-modified trehalose (TreAz) analogues. Subsequent bioorthogonal ligation with alkyne-functionalized probes enabled detection and visualization of cell-surface glycolipids. Characterization of the metabolic fates of four TreAz analogues revealed unique labeling routes that can be harnessed for pathway-targeted investigation of the mycobacterial trehalome.
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spelling pubmed-34660192012-10-08 Probing the Mycobacterial Trehalome with Bioorthogonal Chemistry Swarts, Benjamin M. Holsclaw, Cynthia M. Jewett, John C. Alber, Marina Fox, Douglas M. Siegrist, M. Sloan Leary, Julie A. Kalscheuer, Rainer Bertozzi, Carolyn R. J Am Chem Soc [Image: see text] Mycobacteria, including the pathogen Mycobacterium tuberculosis, use the non-mammalian disaccharide trehalose as a precursor for essential cell-wall glycolipids and other metabolites. Here we describe a strategy for exploiting trehalose metabolic pathways to label glycolipids in mycobacteria with azide-modified trehalose (TreAz) analogues. Subsequent bioorthogonal ligation with alkyne-functionalized probes enabled detection and visualization of cell-surface glycolipids. Characterization of the metabolic fates of four TreAz analogues revealed unique labeling routes that can be harnessed for pathway-targeted investigation of the mycobacterial trehalome. American Chemical Society 2012-09-14 2012-10-03 /pmc/articles/PMC3466019/ /pubmed/22978752 http://dx.doi.org/10.1021/ja3062419 Text en Copyright © 2012 American Chemical Society http://pubs.acs.org This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org.
spellingShingle Swarts, Benjamin M.
Holsclaw, Cynthia M.
Jewett, John C.
Alber, Marina
Fox, Douglas M.
Siegrist, M. Sloan
Leary, Julie A.
Kalscheuer, Rainer
Bertozzi, Carolyn R.
Probing the Mycobacterial Trehalome with Bioorthogonal Chemistry
title Probing the Mycobacterial Trehalome with Bioorthogonal Chemistry
title_full Probing the Mycobacterial Trehalome with Bioorthogonal Chemistry
title_fullStr Probing the Mycobacterial Trehalome with Bioorthogonal Chemistry
title_full_unstemmed Probing the Mycobacterial Trehalome with Bioorthogonal Chemistry
title_short Probing the Mycobacterial Trehalome with Bioorthogonal Chemistry
title_sort probing the mycobacterial trehalome with bioorthogonal chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3466019/
https://www.ncbi.nlm.nih.gov/pubmed/22978752
http://dx.doi.org/10.1021/ja3062419
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