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Literature summary for 3.4.21.105 extracted from

  • Pierrat, O.A.; Strisovsky, K.; Christova, Y.; Large, J.; Ansell, K.; Bouloc, N.; Smiljanic, E.; Freeman, M.
    Monocyclic beta-lactams are selective, mechanism-based inhibitors of rhomboid intramembrane proteases (2011), ACS Chem. Biol., 6, 325-335.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli C43(DE3) cells Escherichia coli
expressed in Escherichia coli C43(DE3) cells Providencia stuartii

Protein Variants

Protein Variants Comment Organism
S150A inactive Providencia stuartii
S201A inactive Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
(3S,4S)-1-[(4-chlorophenyl)sulfonyl]-3-methyl-4-phenylazetidin-2-one
-
Escherichia coli
(3S,4S)-1-[(4-chlorophenyl)sulfonyl]-3-methyl-4-phenylazetidin-2-one
-
Providencia stuartii
(3S,4S)-3-methyl-1-[(4-methylphenyl)sulfonyl]-4-phenylazetidin-2-one
-
Providencia stuartii
1-(2,3-dihydro-4H-1,4-benzoxazin-4-yl)-3,3,3-trifluoro-2-(trifluoromethyl)propan-1-one
-
Escherichia coli
1-(2,3-dihydro-4H-1,4-benzoxazin-4-yl)-3,3,3-trifluoro-2-(trifluoromethyl)propan-1-one
-
Providencia stuartii
1-(biphenyl-3-ylsulfonyl)-4-phenylazetidin-2-one
-
Escherichia coli
1-(biphenyl-3-ylsulfonyl)-4-phenylazetidin-2-one
-
Providencia stuartii
1-(biphenyl-4-ylsulfonyl)-4-phenylazetidin-2-one
-
Escherichia coli
1-(biphenyl-4-ylsulfonyl)-4-phenylazetidin-2-one
-
Providencia stuartii
1-[(3'-methylbiphenyl-4-yl)sulfonyl]-4-phenylazetidin-2-one
-
Escherichia coli
1-[(3'-methylbiphenyl-4-yl)sulfonyl]-4-phenylazetidin-2-one
-
Providencia stuartii
1-[(3-bromophenyl)sulfonyl]-4-phenylazetidin-2-one
-
Escherichia coli
1-[(3-bromophenyl)sulfonyl]-4-phenylazetidin-2-one
-
Providencia stuartii
1-[(3-chlorophenyl)sulfonyl]-4-(2-phenylethyl)azetidin-2-one
-
Escherichia coli
1-[(3-chlorophenyl)sulfonyl]-4-(2-phenylethyl)azetidin-2-one
-
Providencia stuartii
1-[(3-chlorophenyl)sulfonyl]-4-(propan-2-yl)azetidin-2-one
-
Escherichia coli
1-[(3-chlorophenyl)sulfonyl]-4-(propan-2-yl)azetidin-2-one
-
Providencia stuartii
1-[(4'-chlorobiphenyl-4-yl)sulfonyl]-4-phenylazetidin-2-one
-
Escherichia coli
1-[(4'-chlorobiphenyl-4-yl)sulfonyl]-4-phenylazetidin-2-one
-
Providencia stuartii
1-[(4-bromophenyl)sulfonyl]-4-phenylazetidin-2-one
-
Escherichia coli
1-[(4-bromophenyl)sulfonyl]-4-phenylazetidin-2-one
-
Providencia stuartii
1-[(4-chlorophenyl)sulfonyl]-3-methylazetidin-2-one
-
Escherichia coli
1-[(4-chlorophenyl)sulfonyl]-3-methylazetidin-2-one
-
Providencia stuartii
1-[(4-methylphenyl)sulfonyl]-4-phenylazetidin-2-one
-
Escherichia coli
1-[(4-methylphenyl)sulfonyl]-4-phenylazetidin-2-one
-
Providencia stuartii
3,3,3-trifluoro-N-[(5-methyl-2-phenyl-2H-1,2,3-triazol-4-yl)methyl]-2-(trifluoromethyl)propanamide
-
Escherichia coli
3,3,3-trifluoro-N-[(5-methyl-2-phenyl-2H-1,2,3-triazol-4-yl)methyl]-2-(trifluoromethyl)propanamide
-
Providencia stuartii
3,3,3-trifluoro-N-[2-(propan-2-yloxy)phenyl]-2-(trifluoromethyl)propanamide
-
Escherichia coli
3,3,3-trifluoro-N-[2-(propan-2-yloxy)phenyl]-2-(trifluoromethyl)propanamide
-
Providencia stuartii
3-methyl-1-[(4-methylphenyl)sulfonyl]-4-phenylazetidin-2-one
-
Escherichia coli
4-(2-chlorophenyl)-1-[(3-chlorophenyl)sulfonyl]azetidin-2-one
-
Escherichia coli
4-(2-chlorophenyl)-1-[(3-chlorophenyl)sulfonyl]azetidin-2-one
-
Providencia stuartii
4-(3-bromophenyl)-1-[(3-chlorophenyl)sulfonyl]azetidin-2-one
-
Escherichia coli
4-(3-bromophenyl)-1-[(3-chlorophenyl)sulfonyl]azetidin-2-one
-
Providencia stuartii
4-[(3-methyl-2-oxoazetidin-1-yl)sulfonyl]benzonitrile
-
Escherichia coli
4-[(3-methyl-2-oxoazetidin-1-yl)sulfonyl]benzonitrile
-
Providencia stuartii
benzyl (2S)-1-[(4-methylphenyl)sulfonyl]-4-oxoazetidine-2-carboxylate
-
Escherichia coli
benzyl (2S)-1-[(4-methylphenyl)sulfonyl]-4-oxoazetidine-2-carboxylate
-
Providencia stuartii
N-(2,6-dimethylphenyl)-3,3,3-trifluoro-2-(trifluoromethyl)propanamide
-
Escherichia coli
N-(2,6-dimethylphenyl)-3,3,3-trifluoro-2-(trifluoromethyl)propanamide
-
Providencia stuartii
N-[2-(cyclopentyloxy)phenyl]-3,3,3-trifluoro-2-(trifluoromethyl)propanamide
-
Escherichia coli
N-[2-(cyclopentyloxy)phenyl]-3,3,3-trifluoro-2-(trifluoromethyl)propanamide
-
Providencia stuartii
N-[2-(cyclopropylmethoxy)phenyl]-3,3,3-trifluoro-2-(trifluoromethyl)propanamide
-
Escherichia coli
N-[2-(cyclopropylmethoxy)phenyl]-3,3,3-trifluoro-2-(trifluoromethyl)propanamide
-
Providencia stuartii
phenyl 2-oxo-4-phenylazetidine-1-carboxylate
-
Escherichia coli
phenyl 2-oxo-4-phenylazetidine-1-carboxylate
-
Providencia stuartii
tert-butyl 2-[[3,3,3-trifluoro-2-(trifluoromethyl)propanoyl]amino]benzoate
-
Escherichia coli
tert-butyl 2-[[3,3,3-trifluoro-2-(trifluoromethyl)propanoyl]amino]benzoate
-
Providencia stuartii

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
Gurken protein + H2O Escherichia coli
-
PQRKVRMA + HIVFSFFV
-
?
Gurken protein + H2O Providencia stuartii
-
PQRKVRMA + HIVFSFFV
-
?
Gurken protein + H2O Escherichia coli NR698
-
PQRKVRMA + HIVFSFFV
-
?
LacYTM2 protein + H2O Escherichia coli
-
DINHISKS + DTGIIFAA
-
?
LacYTM2 protein + H2O Providencia stuartii
-
DINHISKS + DTGIIFAA
-
?
LacYTM2 protein + H2O Escherichia coli NR698
-
DINHISKS + DTGIIFAA
-
?
TatA protein + H2O Escherichia coli
-
MESTIATA + AFGSPWQL
-
?
TatA protein + H2O Providencia stuartii
-
MESTIATA + AFGSPWQL
-
?
TatA protein + H2O Escherichia coli NR698
-
MESTIATA + AFGSPWQL
-
?

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-
Escherichia coli NR698
-
-
-
Providencia stuartii
-
-
-

Purification (Commentary)

Purification (Comment) Organism
His-Pure Cobalt affinity column chromatography Escherichia coli
His-Pure Cobalt affinity column chromatography Providencia stuartii

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
Gurken protein + H2O
-
Escherichia coli PQRKVRMA + HIVFSFFV
-
?
Gurken protein + H2O
-
Providencia stuartii PQRKVRMA + HIVFSFFV
-
?
Gurken protein + H2O
-
Escherichia coli NR698 PQRKVRMA + HIVFSFFV
-
?
LacYTM2 protein + H2O
-
Escherichia coli DINHISKS + DTGIIFAA
-
?
LacYTM2 protein + H2O
-
Providencia stuartii DINHISKS + DTGIIFAA
-
?
LacYTM2 protein + H2O
-
Escherichia coli NR698 DINHISKS + DTGIIFAA
-
?
N-acetyl-PEG4-QRKVRMAHIVFSFPC-amide + H2O i.e. peptide KSp21 Escherichia coli N-acetyl-PEG4-QRKVRMA + HIVFSFPC-amide
-
?
N-acetyl-PEG4-QRKVRMAHIVFSFPC-amide + H2O i.e. peptide KSp21 Providencia stuartii N-acetyl-PEG4-QRKVRMA + HIVFSFPC-amide
-
?
N-acetyl-PEG4-QRKVRMAHIVFSFPC-amide + H2O i.e. peptide KSp21 Escherichia coli NR698 N-acetyl-PEG4-QRKVRMA + HIVFSFPC-amide
-
?
TatA protein + H2O
-
Escherichia coli MESTIATA + AFGSPWQL
-
?
TatA protein + H2O
-
Providencia stuartii MESTIATA + AFGSPWQL
-
?
TatA protein + H2O
-
Escherichia coli NR698 MESTIATA + AFGSPWQL
-
?

Synonyms

Synonyms Comment Organism
AarA
-
Providencia stuartii
GlpG
-
Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.001
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii N-[2-(cyclopropylmethoxy)phenyl]-3,3,3-trifluoro-2-(trifluoromethyl)propanamide
0.0013
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii tert-butyl 2-[[3,3,3-trifluoro-2-(trifluoromethyl)propanoyl]amino]benzoate
0.0018
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii N-[2-(cyclopentyloxy)phenyl]-3,3,3-trifluoro-2-(trifluoromethyl)propanamide
0.0023
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 3,3,3-trifluoro-N-[2-(propan-2-yloxy)phenyl]-2-(trifluoromethyl)propanamide
0.0033
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 3,3,3-trifluoro-N-[(5-methyl-2-phenyl-2H-1,2,3-triazol-4-yl)methyl]-2-(trifluoromethyl)propanamide
0.0038
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 1-(2,3-dihydro-4H-1,4-benzoxazin-4-yl)-3,3,3-trifluoro-2-(trifluoromethyl)propan-1-one
0.0068
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 4-(3-bromophenyl)-1-[(3-chlorophenyl)sulfonyl]azetidin-2-one
0.014
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 1-(biphenyl-3-ylsulfonyl)-4-phenylazetidin-2-one
0.016
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 1-[(3-bromophenyl)sulfonyl]-4-phenylazetidin-2-one
0.017
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii N-(2,6-dimethylphenyl)-3,3,3-trifluoro-2-(trifluoromethyl)propanamide
0.0183
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 4-(2-chlorophenyl)-1-[(3-chlorophenyl)sulfonyl]azetidin-2-one
0.02
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 4-[(3-methyl-2-oxoazetidin-1-yl)sulfonyl]benzonitrile
0.026
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 1-[(4-bromophenyl)sulfonyl]-4-phenylazetidin-2-one
0.026
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 1-[(4-chlorophenyl)sulfonyl]-3-methylazetidin-2-one
0.029
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii benzyl (2S)-1-[(4-methylphenyl)sulfonyl]-4-oxoazetidine-2-carboxylate
0.03
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii (3S,4S)-3-methyl-1-[(4-methylphenyl)sulfonyl]-4-phenylazetidin-2-one
0.033
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 1-[(3-chlorophenyl)sulfonyl]-4-(2-phenylethyl)azetidin-2-one
0.041
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 1-(biphenyl-4-ylsulfonyl)-4-phenylazetidin-2-one
0.043
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 1-[(3'-methylbiphenyl-4-yl)sulfonyl]-4-phenylazetidin-2-one
0.047
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 1-[(4'-chlorobiphenyl-4-yl)sulfonyl]-4-phenylazetidin-2-one
0.07
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii (3S,4S)-1-[(4-chlorophenyl)sulfonyl]-3-methyl-4-phenylazetidin-2-one
0.074
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 1-[(4-methylphenyl)sulfonyl]-4-phenylazetidin-2-one
0.085
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii 1-[(3-chlorophenyl)sulfonyl]-4-(propan-2-yl)azetidin-2-one
0.182
-
25 mM HEPES, pH 7.4, 5 mM EDTA, 5% (v/v) glycerol, 0.5% (w/v) DDM, 20% (v/v) DMSO, at 25°C Providencia stuartii phenyl 2-oxo-4-phenylazetidine-1-carboxylate