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Literature summary for 3.5.1.108 extracted from

  • Jana, S.; Loeppenberg, M.; Daniliuc, C.; Holl, R.
    C-Triazolyl beta-D-furanosides as LpxC inhibitors: stereoselective synthesis and biological valuation (2014), Tetrahedron, 70, 6569-6577.
No PubMed abstract available
Search for more literature for 3.5.1.108

Inhibitors

Inhibitors Comment Organism Structure
(2S,3R,4S,5S)-5-(1-benzyl-1H-1,2,3-triazol-4-yl)-N,3,4-trihydroxytetrahydrofuran-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5S)-5-[1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl]-N,3,4-trihydroxytetrahydrofuran-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(1-phenethyl-1H-1,2,3-triazol-4-yl)tetrahydrofuran-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(1-phenyl-1H-1,2,3-triazol-4-yl)tetrahydrofuran-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(1-[4-(trifluoromethyl)benzyl]-1H-1,2,3-triazol-4-yl)tetrahydrofuran-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]tetrahydrofuran-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-[4-(4-phenylbuta-1,3-diyn-1-yl)phenyl]oxolane-2-carboxamide
-
 Escherichia coli
additional information C-triazolyl beta-D-furanosides as LpxC inhibitors, stereoselective synthesis and evaluation, biological activity against Escherichia coli strains BL21(DE3) and D22, overview Escherichia coli
N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-((4-[(morpholin-4-yl)methyl]phenyl)ethynyl)benzamide
-
 Escherichia coli

Metals/Ions

Metals/Ions Comment Organism Structure
Zn2+ Zn2+-dependent enzyme Escherichia coli

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine + H2O Escherichia coli
-
 UDP-3-O-[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + acetate
-
 ?

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
 gene lpxC
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine + H2O
-
 Escherichia coli UDP-3-O-[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + acetate
-
 ?

Synonyms

Synonyms Comment Organism
LpxC
-
 Escherichia coli

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000008
-
 N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-((4-[(morpholin-4-yl)methyl]phenyl)ethynyl)benzamide pH 6.0, 37°C Escherichia coli
0.0044
-
 (2S,3R,4S,5S)-N,3,4-trihydroxy-5-[4-(4-phenylbuta-1,3-diyn-1-yl)phenyl]oxolane-2-carboxamide pH 6.0, 37°C Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00006
-
 pH 6.0, 37°C Escherichia coli N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-((4-[(morpholin-4-yl)methyl]phenyl)ethynyl)benzamide
0.032
-
 pH 6.0, 37°C Escherichia coli (2S,3R,4S,5S)-N,3,4-trihydroxy-5-[4-(4-phenylbuta-1,3-diyn-1-yl)phenyl]oxolane-2-carboxamide
0.2
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5S)-5-(1-benzyl-1H-1,2,3-triazol-4-yl)-N,3,4-trihydroxytetrahydrofuran-2-carboxamide
0.2
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5S)-5-[1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl]-N,3,4-trihydroxytetrahydrofuran-2-carboxamide
0.2
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5S)-N,3,4-trihydroxy-5-(1-phenethyl-1H-1,2,3-triazol-4-yl)tetrahydrofuran-2-carboxamide
0.2
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5S)-N,3,4-trihydroxy-5-(1-phenyl-1H-1,2,3-triazol-4-yl)tetrahydrofuran-2-carboxamide
0.2
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5S)-N,3,4-trihydroxy-5-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]tetrahydrofuran-2-carboxamide
0.2
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5S)-N,3,4-trihydroxy-5-(1-[4-(trifluoromethyl)benzyl]-1H-1,2,3-triazol-4-yl)tetrahydrofuran-2-carboxamide

General Information

General Information Comment Organism
metabolism the enzyme plays an important role in the biosynthesis of lipid A Escherichia coli