Chemical synthesis of the organoarsenical antibiotic arsinothricin

Authors

A. Hasan Howlader, Florida International University
Sazzad H. Suzol, Florida International University
Venkadesh Sarkarai Nadar, Herbert Wertheim College of Medicine
Adriana Emilce Galván, Herbert Wertheim College of Medicine
Aleksandra Nedovic, Florida Atlantic University
Predrag Cudic, Florida Atlantic University
Barry P. Rosen, Herbert Wertheim College of Medicine
Masafumi Yoshinaga, Herbert Wertheim College of Medicine
Stanislaw F. Wnuk, Florida International University

Date of this Version

10-25-2021

Document Type

Article

Abstract

We report two routes of chemical synthesis of arsinothricin (AST), the novel organoarsenical antibiotic. One is by condensation of the 2-chloroethyl(methyl)arsinic acid with acetamidomalonate, and the second involves reduction of the N-acetyl protected derivative of hydroxyarsinothricin (AST-OH) and subsequent methylation of a trivalent arsenic intermediate with methyl iodide. The enzyme AST N-acetyltransferase (ArsN1) was utilized to purify l-AST from racemic AST. This chemical synthesis provides a source of this novel antibiotic for future drug development.

DOI

10.1039/d1ra06770b

Recommended Citation

Howlader, A. Hasan; Suzol, Sazzad H.; Nadar, Venkadesh Sarkarai; Galván, Adriana Emilce; Nedovic, Aleksandra; Cudic, Predrag; Rosen, Barry P.; Yoshinaga, Masafumi; and Wnuk, Stanislaw F., "Chemical synthesis of the organoarsenical antibiotic arsinothricin" (2021). All Faculty. 310.
https://digitalcommons.fiu.edu/all_faculty/310