Abstract
Genomic studies revealed the absence of glutaminyl-tRNA synthetase and/or asparaginyl-tRNA synthetase in many bacteria and all known archaea. In these microorganisms, glutaminyl-tRNA Gln (Gln-tRNA Gln) and/or asparaginyl-tRNA Asn (Asn-tRNA Asn) are synthesized via an indirect pathway involving side chain amidation of misacylated glutamyl-tRNA Gln (Glu-tRNA Gln) and/or aspartyl-tRNA Asn (Asp-tRNA Asn) by an amidotransferase. A series of chloramphenicol analogs have been synthesized and evaluated as inhibitors of Helicobacter pylori GatCAB amidotransferase. Compound 7a was identified as the most active competitive inhibitor of the transamidase activity with respect to Asp-tRNA Asn ( K m = 2 μM), with a K i value of 27 μM.
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