N-Alkoxysulfamide, N-hydroxysulfamide, and sulfamate analogues of methionyl and isoleucyl adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases

  • Bioorg Med Chem Lett. 2003 Mar 24;13(6):1087-92. doi: 10.1016/s0960-894x(03)00020-9.
Jeewoo Lee  1 ,  Sung Eun Kim ,  Ji Young Lee ,  Su Yeon Kim ,  Sang Uk Kang ,  Seung Hwan Seo ,  Moon Woo Chun ,  Taehee Kang ,  Soo Young Choi ,  Hea Ok Kim
Affiliations
  • 1. Laboratory of Medicinal Chemistry, RIPS, College of Pharmacy, Seoul National University, Seoul 151-742, South Korea.
PMID: 12643918 DOI: 10.1016/s0960-894x(03)00020-9
Abstract

A series of sulfamate surrogates of methionyl and isoleucyl adenylate have been investigated as MetRS and IleRS inhibitors by modifications of the sulfamate linker and adenine moieties. The discovery of 2-iodo Ile-NHSO(2)-AMP (58) as a potent Escherichia coli IleRS inhibitor revealed that a significant hydrophobic interaction between the 2-substituent of Ile-NHSO(2)-AMP and the adenine binding site of IleRS provided its high potency to the enzyme.

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