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Literature summary for 3.5.1.108 extracted from

  • Jana, S.; Loeppenberg, M.; Daniliuc, C.; Jose, J.; Holl, R.
    Development of novel LpxC inhibitors: chiral-pool synthesis of C-triazolyl glycosides (2013), Tetrahedron, 69, 9434-9442.
No PubMed abstract available
Search for more literature for 3.5.1.108

Inhibitors

Inhibitors Comment Organism Structure
(2S,3R,4S,5R)-5-(1-benzyl-1H-1,2,3-triazol-4-yl)-N,3,4-trihydroxyoxolane-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5R)-5-(1-hexyl-1H-1,2,3-triazol-4-yl)-N,3,4-trihydroxyoxolane-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5R)-5-[1-[(4-fluorophenyl)methyl]-1H-1,2,3-triazol-4-yl]-N,3,4-trihydroxyoxolane-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(1-phenyl-1H-1,2,3-triazol-4-yl)oxolane-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(1-[[4-(trifluoromethyl)phenyl]methyl]-1H-1,2,3-triazol-4-yl)oxolane-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-[1-(2-phenylethyl)-1H-1,2,3-triazol-4-yl]oxolane-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]oxolane-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-[4-([4-[(morpholin-4-yl)methyl]phenyl]ethynyl)phenyl]oxolane-2-carboxamide
-
 Escherichia coli
additional information development of novel LpxC inhibitors, chiral-pool synthesis of C-triazolyl glycosides, 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

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
0.2
-
 pH 6.0, 37°C Escherichia coli (2S,3R,4S,5R)-5-(1-benzyl-1H-1,2,3-triazol-4-yl)-N,3,4-trihydroxyoxolane-2-carboxamide
0.2
-
 pH 6.0, 37°C Escherichia coli (2S,3R,4S,5R)-5-(1-hexyl-1H-1,2,3-triazol-4-yl)-N,3,4-trihydroxyoxolane-2-carboxamide
0.2
-
 pH 6.0, 37°C Escherichia coli (2S,3R,4S,5R)-5-[1-[(4-fluorophenyl)methyl]-1H-1,2,3-triazol-4-yl]-N,3,4-trihydroxyoxolane-2-carboxamide
0.2
-
 pH 6.0, 37°C Escherichia coli (2S,3R,4S,5R)-N,3,4-trihydroxy-5-(1-phenyl-1H-1,2,3-triazol-4-yl)oxolane-2-carboxamide
0.2
-
 pH 6.0, 37°C Escherichia coli (2S,3R,4S,5R)-N,3,4-trihydroxy-5-(1-[[4-(trifluoromethyl)phenyl]methyl]-1H-1,2,3-triazol-4-yl)oxolane-2-carboxamide
0.2
-
 pH 6.0, 37°C Escherichia coli (2S,3R,4S,5R)-N,3,4-trihydroxy-5-[1-(2-phenylethyl)-1H-1,2,3-triazol-4-yl]oxolane-2-carboxamide
0.2
-
 pH 6.0, 37°C Escherichia coli (2S,3R,4S,5R)-N,3,4-trihydroxy-5-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]oxolane-2-carboxamide
0.2
-
 pH 6.0, 37°C Escherichia coli (2S,3R,4S,5S)-N,3,4-trihydroxy-5-[4-([4-[(morpholin-4-yl)methyl]phenyl]ethynyl)phenyl]oxolane-2-carboxamide