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Literature summary extracted from

  • Pieroni, M.; Annunziato, G.; Beato, C.; Wouters, R.; Benoni, R.; Campanini, B.; Pertinhez, T.A.; Bettati, S.; Mozzarelli, A.; Costantino, G.
    Rational design, synthesis, and preliminary structure-activity relationships of alpha-substituted-2-phenylcyclopropane carboxylic acids as inhibitors of Salmonella typhimurium O-acetylserine sulfhydrylase (2016), J. Med. Chem., 59, 2567-2578.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.5.1.47 (1R,2R)-1-(4-chlorobenzyl)-2-phenylcyclopropanecarboxylic acid
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 (1R,2R)-1-(4-methylbenzyl)-2-phenylcyclopropanecarboxylic acid
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 (1R,2R)-1-benzyl-2-phenylcyclopropanecarboxylic acid
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 (1R,2S)-1-ethyl-2-phenylcyclopropanecarboxylic acid
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 (1S,2R)-1-ethyl-2-phenylcyclopropanecarboxylic acid
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 (1S,2S)-1-(4-chlorobenzyl)-2-phenylcyclopropanecarboxylic acid
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 (1S,2S)-1-(4-methylbenzyl)-2-phenylcyclopropanecarboxylic acid
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 (1S,2S)-1-benzyl-2-phenylcyclopropanecarboxylic acid
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 additional information computational and spectroscopic approaches to rationally design, synthesize, and test a series of substituted 2-phenylcyclopropane carboxylic acids that bind to the two Salmonella typhymurium OASS isoforms at nanomolar concentrations, Kd values and binding structures, molecular modeling and docking study, overview; computational and spectroscopic approaches to rationally design, synthesize, and test a series of substituted 2-phenylcyclopropane carboxylic acids that bind to the two Salmonella typhymurium OASS isoforms at nanomolar concentrations, Kd values and binding structures, molecular modeling and docking study, overview Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 trans-1-(4-chlorobenzyl)-2-phenylcyclopropanecarboxylic acid
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 trans-1-(4-methylbenzyl)-2-phenylcyclopropanecarboxylic acid
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 trans-1-benzyl-2-phenylcyclopropanecarboxylic acid
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 trans-1-ethyl-2-phenylcyclopropanecarboxylic acid
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 trans-1-phenethyl-2-phenylcyclopropanecarboxylic acid
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 trans-2-phenylcyclopropanecarboxylic acid
-
 Salmonella enterica subsp. enterica serovar Typhimurium

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.5.1.47 O-acetyl-L-serine + hydrogen sulfide Salmonella enterica subsp. enterica serovar Typhimurium
-
 L-cysteine + acetate
-
 ?
2.5.1.47 O-acetyl-L-serine + hydrogen sulfide Salmonella enterica subsp. enterica serovar Typhimurium ATCC 700720
-
 L-cysteine + acetate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.47 Salmonella enterica subsp. enterica serovar Typhimurium P0A1E3 isozyme OASS-A
-
2.5.1.47 Salmonella enterica subsp. enterica serovar Typhimurium P29848 isozyme OASS-B
-
2.5.1.47 Salmonella enterica subsp. enterica serovar Typhimurium ATCC 700720 P0A1E3 isozyme OASS-A
-
2.5.1.47 Salmonella enterica subsp. enterica serovar Typhimurium ATCC 700720 P29848 isozyme OASS-B
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.47 O-acetyl-L-serine + hydrogen sulfide
-
 Salmonella enterica subsp. enterica serovar Typhimurium L-cysteine + acetate
-
 ?
2.5.1.47 O-acetyl-L-serine + hydrogen sulfide
-
 Salmonella enterica subsp. enterica serovar Typhimurium ATCC 700720 L-cysteine + acetate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.5.1.47 cysK
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 CysM
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 cysteine synthase A
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 cysteine synthase B
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 O-acetylserine sulfhydrylase
-
 Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 OASS
-
 Salmonella enterica subsp. enterica serovar Typhimurium

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.5.1.47 20 25 assay at Salmonella enterica subsp. enterica serovar Typhimurium

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.5.1.47 7
-
 assay at Salmonella enterica subsp. enterica serovar Typhimurium

Cofactor

EC Number Cofactor Comment Organism Structure
2.5.1.47 pyridoxal 5'-phosphate dependent on Salmonella enterica subsp. enterica serovar Typhimurium

General Information

EC Number General Information Comment Organism
2.5.1.47 evolution O-acetylserine sulfydrylase, a highly conserved pyridoxal 5'-phosphate-dependent enzyme, present in different isoforms in bacteria, plants, and nematodes, but absent in mammals Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 metabolism the enzyme catalyzes the last step of cysteine biosynthesis. Cysteine is a building block for several biomolecules that are crucial for living organisms Salmonella enterica subsp. enterica serovar Typhimurium
2.5.1.47 physiological function beside the biosynthesis of cysteine, enzyme OASS exerts a series of moonlighting activities in bacteria, such as transcriptional regulation, contact-dependent growth inhibition, swarming motility, and induction of antibiotic resistance Salmonella enterica subsp. enterica serovar Typhimurium