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Bioorthogonal Chemical Reporters for Selective In Situ Probing of Mycomembrane Components in Mycobacteria
Author(s) -
Foley Hannah N.,
Stewart Jessica A.,
Kavunja Herbert W.,
Rundell Sarah R.,
Swarts Benjamin M.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201509216
Subject(s) - bioorthogonal chemistry , covalent bond , context (archaeology) , chemistry , arabinogalactan , mycobacterium tuberculosis , mycobacterium , biochemistry , glycolipid , cell wall , biology , tuberculosis , combinatorial chemistry , click chemistry , bacteria , organic chemistry , pathology , medicine , paleontology , genetics
The global pathogen Mycobacterium tuberculosis and other species in the suborder Corynebacterineae possess a distinctive outer membrane called the mycomembrane (MM). The MM is composed of mycolic acids, which are either covalently linked to an underlying arabinogalactan layer or incorporated into trehalose glycolipids that associate with the MM non‐covalently. These structures are generated through a process called mycolylation, which is central to mycobacterial physiology and pathogenesis and is an important target for tuberculosis drug development. Current approaches to investigating mycolylation rely on arduous analytical methods that occur outside the context of a whole cell. Herein, we describe mycobacteria‐specific chemical reporters that can selectively probe either covalent arabinogalactan mycolates or non‐covalent trehalose mycolates in live mycobacteria. These probes, in conjunction with bioorthogonal chemistry, enable selective in situ detection of the major MM components.