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


Authors: Kinarivala, N.; Standke, L. C.; Guney, T.; Ji, C.; Noguchi, N.; Asano, Y.; Tan, D. S.
Article Title: Gram-scale preparation of the antibiotic lead compound salicyl-AMS, a potent inhibitor of bacterial salicylate adenylation enzymes
Abstract: 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.
Keywords: unclassified drug; drug structure; enzyme inhibitor; drug development; drug synthesis; biosynthesis; adenosine; sodium; bacterium; tuberculosis; adenylation; drug purification; salicylic acid; antibiotic; siderophore; tuberculostatic agent; n hydroxysuccinimide; adenosine 2 3 acetonide; salicylams
Journal Title: Methods in Enzymology
Volume: 638
ISSN: 0076-6879
Publisher: Academic Press  
Date Published: 2020-01-01
Start Page: 69
End Page: 87
Language: English
DOI: 10.1016/bs.mie.2020.04.051
PUBMED: 32416922
PROVIDER: scopus
DOI/URL:
Notes: Book Chapter 4 in " Chemical Tools for Imaging, Manipulating, and Tracking Biological Systems: Diverse Methods for Prokaryotic and Eukaryotic Systems" Chenoweth DM, ed (ISBN: 978-0-12-820145-9)-- Export Date: 1 June 2020 -- Source: Scopus
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MSK Authors
  1. Derek S Tan
    74 Tan
  2. Cheng   Ji
    4 Ji
  3. Tezcan   Guney
    5 Guney