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 |
PMCID: | PMC7367610 |
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 |