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Literature summary extracted from

  • Ziebart, K.T.; Dixon, S.M.; Avila, B.; El-Badri, M.H.; Guggenheim, K.G.; Kurth, M.J.; Toney, M.D.
    Targeting multiple chorismate-utilizing enzymes with a single inhibitor: validation of a three-stage design (2010), J. Med. Chem., 53, 3718-3729.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.1.3.27 partial complex anthranilate synthase expressed in Escherichia coli CB694 Salmonella enterica subsp. enterica serovar Typhimurium

Inhibitors

EC Number Inhibitors Comment Organism Structure
4.1.3.27 (3-carbamoylphenoxy)acetic acid
-
Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 (3-[[(5S)-6-([2-[6-(3-amino-3-oxopropyl)dibenzo[b,d]furan-4-yl]ethyl]amino)-5-[[2-(4-nitrophenyl)propanoyl]amino]-6-oxohexyl]carbamoyl]phenoxy)acetic acid
-
Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 2-(3-(-(S)-5-((S)-1-amino-3-(3-chlorophenyl)-1-oxopropan-2-ylamino)-4-(3-hydroxy-4-methyl-2-nitrobenzamido)-5-oxopentylcarbamoyl)-phenoxy)acetic acid
-
Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 2-(3-(3-((R)-3-((S)-1-amino-3-(3-chlorophenyl)-1-oxopropan-2-ylamino)-2-(3-hydroxy-4-methyl-2-nitrobenzamido)-3-oxopropylthio) propylcarbamoyl)phenoxy)acetic acid
-
Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 3-(carboxymethoxy)benzoic acid
-
Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 N-((S)-1-((S)-1-amino-3-(3-chlorophenyl)-1-oxopropan-2-ylamino)-1-oxopropan-2-yl)-3-hydroxy-4-methyl-2-nitrobenzamide
-
Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 N-((S)-6-amino-1-((S)-1-amino-3-(3-chlorophenyl)-1-oxopropan-2-ylamino)-1-oxohexan-2-yl)-3-hydroxy-4-methyl-2-nitrobenzamide
-
Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 N6-[3-(carboxymethoxy)benzoyl]-N2-(2,6-dimethoxybenzoyl)-L-lysyl-3-hydroxy-4-nitro-L-phenylalaninamide
-
Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 N6-[3-(carboxymethoxy)benzoyl]-N2-(3-hydroxy-4-methyl-2-nitrobenzoyl)-L-lysyl-3-chloro-L-phenylalaninamide
-
Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 N6-[3-(carboxymethoxy)benzoyl]-N2-(3-hydroxy-4-methyl-2-nitrobenzoyl)-L-lysyl-4-cyano-L-phenylalaninamide
-
Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 [3-([(5S)-5-[[(3-benzoylpyridin-2-yl)carbonyl]amino]-6-[(1-carbamoylcyclohexyl)amino]-6-oxohexyl]carbamoyl)phenoxy]acetic acid
-
Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 [3-([(5S)-6-[(1-carbamoylcyclohexyl)amino]-5-[(3,5-dihydroxybenzoyl)amino]-6-oxohexyl]carbamoyl)phenoxy]acetic acid
-
Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 [3-([(5S)-6-[(4-carbamoyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)amino]-6-oxo-5-[(4-phenoxybenzoyl)amino]hexyl]carbamoyl)phenoxy]acetic acid
-
Salmonella enterica subsp. enterica serovar Typhimurium

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
4.1.3.27 0.0039
-
chorismate saturating Mg2+, pH 7.0, 25°C Salmonella enterica subsp. enterica serovar Typhimurium

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
4.1.3.27 Mg2+
-
Salmonella enterica subsp. enterica serovar Typhimurium

Organism

EC Number Organism UniProt Comment Textmining
4.1.3.27 Salmonella enterica subsp. enterica serovar Typhimurium
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
4.1.3.27 ammonium sulfate precipitation, ion exchange chromatography Salmonella enterica subsp. enterica serovar Typhimurium

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.1.3.27 chorismate + L-glutamine
-
Salmonella enterica subsp. enterica serovar Typhimurium anthranilate + pyruvate + L-glutamate
-
?

Subunits

EC Number Subunits Comment Organism
4.1.3.27 More partial complex anthranilate synthase consists of two TrpE:TrpG heterodimers Salmonella enterica subsp. enterica serovar Typhimurium

Synonyms

EC Number Synonyms Comment Organism
4.1.3.27 anthranilate synthase
-
Salmonella enterica subsp. enterica serovar Typhimurium

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
4.1.3.27 0.02
-
N6-[3-(carboxymethoxy)benzoyl]-N2-(3-hydroxy-4-methyl-2-nitrobenzoyl)-L-lysyl-3-chloro-L-phenylalaninamide inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.028
-
N6-[3-(carboxymethoxy)benzoyl]-N2-(3-hydroxy-4-methyl-2-nitrobenzoyl)-L-lysyl-4-cyano-L-phenylalaninamide inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.041
-
2-(3-(-(S)-5-((S)-1-amino-3-(3-chlorophenyl)-1-oxopropan-2-ylamino)-4-(3-hydroxy-4-methyl-2-nitrobenzamido)-5-oxopentylcarbamoyl)-phenoxy)acetic acid inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.054
-
N6-[3-(carboxymethoxy)benzoyl]-N2-(3-hydroxy-4-methyl-2-nitrobenzoyl)-L-lysyl-3-chloro-L-phenylalaninamide inhibitor binding to the enzyme-chorismate complex, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.08
-
N6-[3-(carboxymethoxy)benzoyl]-N2-(2,6-dimethoxybenzoyl)-L-lysyl-3-hydroxy-4-nitro-L-phenylalaninamide inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.081
-
N6-[3-(carboxymethoxy)benzoyl]-N2-(3-hydroxy-4-methyl-2-nitrobenzoyl)-L-lysyl-4-cyano-L-phenylalaninamide inhibitor binding to the enzyme-chorismate complex, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.096
-
2-(3-(3-((R)-3-((S)-1-amino-3-(3-chlorophenyl)-1-oxopropan-2-ylamino)-2-(3-hydroxy-4-methyl-2-nitrobenzamido)-3-oxopropylthio) propylcarbamoyl)phenoxy)acetic acid inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.11
-
N-((S)-6-amino-1-((S)-1-amino-3-(3-chlorophenyl)-1-oxopropan-2-ylamino)-1-oxohexan-2-yl)-3-hydroxy-4-methyl-2-nitrobenzamide inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.11
-
(3-[[(5S)-6-([2-[6-(3-amino-3-oxopropyl)dibenzo[b,d]furan-4-yl]ethyl]amino)-5-[[2-(4-nitrophenyl)propanoyl]amino]-6-oxohexyl]carbamoyl]phenoxy)acetic acid inhibitor binding to the enzyme-chorismate complex, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.16
-
[3-([(5S)-6-[(1-carbamoylcyclohexyl)amino]-5-[(3,5-dihydroxybenzoyl)amino]-6-oxohexyl]carbamoyl)phenoxy]acetic acid inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.2
-
N-((S)-1-((S)-1-amino-3-(3-chlorophenyl)-1-oxopropan-2-ylamino)-1-oxopropan-2-yl)-3-hydroxy-4-methyl-2-nitrobenzamide inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.21
-
3-(carboxymethoxy)benzoic acid inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.25
-
(3-[[(5S)-6-([2-[6-(3-amino-3-oxopropyl)dibenzo[b,d]furan-4-yl]ethyl]amino)-5-[[2-(4-nitrophenyl)propanoyl]amino]-6-oxohexyl]carbamoyl]phenoxy)acetic acid inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.389
-
[3-([(5S)-6-[(1-carbamoylcyclohexyl)amino]-5-[(3,5-dihydroxybenzoyl)amino]-6-oxohexyl]carbamoyl)phenoxy]acetic acid inhibitor binding to the enzyme-chorismate complex, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.49
-
[3-([(5S)-5-[[(3-benzoylpyridin-2-yl)carbonyl]amino]-6-[(1-carbamoylcyclohexyl)amino]-6-oxohexyl]carbamoyl)phenoxy]acetic acid inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.55
-
3-(carboxymethoxy)benzoic acid inhibitor binding to the enzyme-chorismate complex, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.57
-
[3-([(5S)-6-[(4-carbamoyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)amino]-6-oxo-5-[(4-phenoxybenzoyl)amino]hexyl]carbamoyl)phenoxy]acetic acid inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 0.76
-
(3-carbamoylphenoxy)acetic acid inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 1.02
-
[3-([(5S)-6-[(4-carbamoyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)amino]-6-oxo-5-[(4-phenoxybenzoyl)amino]hexyl]carbamoyl)phenoxy]acetic acid inhibitor binding to the enzyme-chorismate complex, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 1.081
-
[3-([(5S)-5-[[(3-benzoylpyridin-2-yl)carbonyl]amino]-6-[(1-carbamoylcyclohexyl)amino]-6-oxohexyl]carbamoyl)phenoxy]acetic acid inhibitor binding to the enzyme-chorismate complex, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
4.1.3.27 2.6
-
(3-carbamoylphenoxy)acetic acid inhibitor binding to the enzyme-chorismate complex, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium