Inhibitors of bacterial tyrosyl tRNA synthetase: synthesis of four stereoisomeric analogues of the natural product SB-219383

Bioorganic & Medicinal Chemistry Letters
2000.0

Abstract

Synthetic analogues of the microbial metabolite SB-219383 have been synthesised with defined stereochemistry. Densely functionalised hydroxylamine containing amino acids were prepared by the addition of a glycine anion equivalent to sugar-derived cyclic nitrones. One of four stereoisomeric dipeptides incorporating these novel amino acids was found to be a potent and selective inhibitor of bacterial tyrosyl tRNA synthetase, suggesting analogous stereochemistry of the natural product.

Knowledge Graph

Similar Paper

Inhibitors of bacterial tyrosyl tRNA synthetase: synthesis of four stereoisomeric analogues of the natural product SB-219383
Bioorganic & Medicinal Chemistry Letters 2000.0
Inhibitors of Bacterial Tyrosyl tRNA Synthetase: Synthesis of Carbocyclic Analogues of the Natural Product SB-219383
Bioorganic & Medicinal Chemistry Letters 2001.0
SB-219383, a Novel Tyrosyl tRNA Synthetase Inhibitor from a Micromonospora sp. II. Structure Determination.
The Journal of Antibiotics 2000.0
SB-219383, a Novel Tyrosyl tRNA Synthetase Inhibitor from a Micromonospora sp. I. Fermentation, Isolation and Properties.
The Journal of Antibiotics 2000.0
A Potent Seryl tRNA Synthetase Inhibitor SB-217452 Isolated from a Streptomyces species.
The Journal of Antibiotics 2000.0
Analogues of SB-203207 as inhibitors of tRNA synthetases
Bioorganic & Medicinal Chemistry Letters 2000.0
SB-203207 and SB-203208, Too Novel Isoleucyl tRNA Synthetase Inhibitors from a Streptomyces sp. II. Structure Determination.
The Journal of Antibiotics 2000.0
Structure-activity dependency of new bacterial tryptophanyl tRNA synthetase inhibitors
Bioorganic & Medicinal Chemistry Letters 1996.0
Tyrosyl-tRNA synthetase inhibitors as antibacterial agents: Synthesis, molecular docking and structure–activity relationship analysis of 3-aryl-4-arylaminofuran-2(5H)-ones
European Journal of Medicinal Chemistry 2011.0
Synthesis and evaluation of new tyrosyl-tRNA synthetase inhibitors as antibacterial agents based on a N2-(arylacetyl)glycinanilide scaffold
European Journal of Medicinal Chemistry 2015.0