1241048-43-0Relevant articles and documents
Rational Design, Synthesis, and Preliminary Structure-Activity Relationships of α-Substituted-2-Phenylcyclopropane Carboxylic Acids as Inhibitors of Salmonella typhimurium O-Acetylserine Sulfhydrylase
Pieroni, Marco,Annunziato, Giannamaria,Beato, Claudia,Wouters, Randy,Benoni, Roberto,Campanini, Barbara,Pertinhez, Thelma A.,Bettati, Stefano,Mozzarelli, Andrea,Costantino, Gabriele
, p. 2567 - 2578 (2016/04/10)
Cysteine is a building block for several biomolecules that are crucial for living organisms. The last step of cysteine biosynthesis is catalyzed by O-acetylserine sulfydrylase (OASS), a highly conserved pyridoxal 5′-phosphate (PLP)-dependent enzyme, present in different isoforms in bacteria, plants, and nematodes, but absent in mammals. Beside the biosynthesis of cysteine, OASS exerts a series of moonlighting activities in bacteria, such as transcriptional regulation, contact-dependent growth inhibition, swarming motility, and induction of antibiotic resistance. Therefore, the discovery of molecules capable of inhibiting OASS would be a valuable tool to unravel how this protein affects the physiology of unicellular organisms. As a continuation of our efforts toward the synthesis of OASS inhibitors, in this work we have used a combination of computational and spectroscopic approaches to rationally design, synthesize, and test a series of substituted 2-phenylcyclopropane carboxylic acids that bind to the two S. typhymurium OASS isoforms at nanomolar concentrations.
Stereocontrolled synthesis of quaternary cyclopropyl esters
Bray, Christopher D.,Minicone, Fabrizio
supporting information; experimental part, p. 5867 - 5869 (2010/10/21)
Treatment of a variety of enantiopure terminal epoxides with the anion of a range of 2-substituted triethylphosphonoacetates leads to an array of quaternary cyclopropyl esters with high yield and diastereocontrol.
