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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 22.

Figure 22.

MandiNAc-based chemical reporters for labeling L. pneumophila LPS O-antigen. (A) Structure of the L. pneumophila LPS O-antigen. (B) Biosynthesis of O-antigen precursor CMP-Leg5Ac7Ac, which arises from a MandiNAc intermediate. Subsequent polymerization of the O-antigen subunit and assembly into mature LPS is shown in Figure 18. (C) Structures and (D) chemical synthesis of azide-modified MandiNAc analogues as chemical reporters for the L. pneumophila LPS O-antigen. Bz, benzoyl; CAN, ceric ammonium nitrate; Ms, mesyl; PMP, para-methoxyphenyl.