Gram-scale preparation of the antibiotic lead compound salicyl-AMS, a potent inhibitor of bacterial salicylate adenylation enzymes.

Salicyl-AMS (1) is a potent inhibitor of salicylate adenylation enzymes used in bacterial siderophore biosynthesis and a promising lead compound for the treatment of tuberculosis. An optimized, multigram synthesis is presented, which provides salicyl-AMS as its sodium salt (1·Na) in three synthetic steps followed by a two-step salt formation process. The synthesis proceeds in 11.6% overall yield from commercially available adenosine 2',3'-acetonide and provides highly purified material. © 2020 Elsevier Inc. All rights reserved.

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Nihar Kinarivala, Lisa C Standke, Tezcan Guney, Cheng Ji, Naoyoshi Noguchi, Yasutomi Asano, Derek S Tan. Gram-scale preparation of the antibiotic lead compound salicyl-AMS, a potent inhibitor of bacterial salicylate adenylation enzymes. Methods in enzymology. 2020;638:69-87

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PMID: 32416922

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