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. Author manuscript; available in PMC: 2023 Feb 9.
Published in final edited form as: Chem Rev. 2021 Dec 14;122(3):3336–3413. doi: 10.1021/acs.chemrev.1c00729

Figure 38.

Figure 38.

O- and N-linked TMM derivatives for selective labeling of mycolate-containing components of the mycomembrane. (A) O-linked TMM derivatives (modified with an unnatural R group) mimic the mycoloyl donor function of TMM and are proposed to undergo periplasmic mycoloyltransferase-catalyzed transfer of their unnatural acyl chain onto mycoloyl acceptors, producing labeled TDM, AGM, proteins, and potentially other mycolate-containing products. (B) N-linked TMM derivatives (modified with an unnatural R group) mimic the mycoloyl acceptor function of TMM and are proposed to undergo periplasmic mycoloyltransferase-catalyzed mycoloylation of their free 6-position hydroxyl group, producing only a labeled version of TDM. Enz, enzyme with mycoloyltransferase activity (e.g., Ag85). (C and D) Structures of published O-linked (C) and N-linked (D) TMM derivatives bearing bioorthogonal functional groups, fluorophores, and photo-cross-linking tags.