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Literature summary for 4.1.3.27 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)

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

Inhibitors

Inhibitors Comment Organism Structure
(3-carbamoylphenoxy)acetic acid
-
Salmonella enterica subsp. enterica serovar Typhimurium
(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
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
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
3-(carboxymethoxy)benzoic acid
-
Salmonella enterica subsp. enterica serovar Typhimurium
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
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
N6-[3-(carboxymethoxy)benzoyl]-N2-(2,6-dimethoxybenzoyl)-L-lysyl-3-hydroxy-4-nitro-L-phenylalaninamide
-
Salmonella enterica subsp. enterica serovar Typhimurium
N6-[3-(carboxymethoxy)benzoyl]-N2-(3-hydroxy-4-methyl-2-nitrobenzoyl)-L-lysyl-3-chloro-L-phenylalaninamide
-
Salmonella enterica subsp. enterica serovar Typhimurium
N6-[3-(carboxymethoxy)benzoyl]-N2-(3-hydroxy-4-methyl-2-nitrobenzoyl)-L-lysyl-4-cyano-L-phenylalaninamide
-
Salmonella enterica subsp. enterica serovar Typhimurium
[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
[3-([(5S)-6-[(1-carbamoylcyclohexyl)amino]-5-[(3,5-dihydroxybenzoyl)amino]-6-oxohexyl]carbamoyl)phenoxy]acetic acid
-
Salmonella enterica subsp. enterica serovar Typhimurium
[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]

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

Metals/Ions

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

Organism

Organism UniProt Comment Textmining
Salmonella enterica subsp. enterica serovar Typhimurium
-
-
-

Purification (Commentary)

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

Substrates and Products (Substrate)

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

Subunits

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

Synonyms

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

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
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
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
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
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
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
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
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
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
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
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
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
0.21
-
3-(carboxymethoxy)benzoic acid inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
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
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
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
0.55
-
3-(carboxymethoxy)benzoic acid inhibitor binding to the enzyme-chorismate complex, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
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
0.76
-
(3-carbamoylphenoxy)acetic acid inhibition with respect to chorismate binding, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium
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
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
2.6
-
(3-carbamoylphenoxy)acetic acid inhibitor binding to the enzyme-chorismate complex, pH 7.8, 25°C Salmonella enterica subsp. enterica serovar Typhimurium