Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 3.5.1.108 extracted from

  • Jana, S.; Loeppenberg, M.; Daniliuc, C.; Holl, R.
    Synthesis and biological evaluation of C-ethynyl furanosides as LpxC inhibitors (2015), Tetrahedron, 71, 956-966.
No PubMed abstract available
Search for more literature for 3.5.1.108

Cloned(Commentary)

Cloned (Comment) Organism
gene lpxC, recombinant expression of enzyme mutant LpxC C63A Escherichia coli

Protein Variants

Protein Variants Comment Organism
C63A site-directed mutagenesis, the C63A mutation lowers the undesired influence of Zn2+-concentration on enzymatic activity Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
(2R)-N-hydroxy-2-(methanesulfonyl)-2-methyl-4-(4-oxo-7-phenylquinazolin-3(4H)-yl)butanamide
-
 Escherichia coli
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(2-(4-[2-(4-methoxyphenyl)ethynyl]phenyl)ethynyl)tetrahydrofuran-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(octa-1,3-diyn-1-yl)tetrahydrofuran-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(phenylbuta-1,3-diyn-1-yl)tetrahydrofuran-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-([4-(phenylethynyl)phenyl]ethynyl)tetrahydrofuran-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-[2-(4-(2-[4-(trifluoromethyl)phenyl]ethynyl)phenyl)ethynyl]tetrahydrofuran-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-((4-[(4-methoxyphenyl)ethynyl]phenyl)ethynyl)tetrahydrofuran-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(phenylbuta-1,3-diyn-1-yl)tetrahydrofuran-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-([4-(phenylethynyl)phenyl]ethynyl)tetrahydrofuran-2-carboxamide
-
 Escherichia coli
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-[(4-([4-(trifluoromethyl)phenyl]ethynyl)phenyl)ethynyl]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 synthesis and biological evaluation of C-ethynyl furanosides as enzyme LpxC inhibitors, 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
-

Purification (Commentary)

Purification (Comment) Organism
recombinant enzyme mutant LpxC C63A by two different steps of anion exchange chromatography, and gel filtration Escherichia coli

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

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Escherichia coli

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6
-
 aassay at 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
0.00402
-
 (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
0.0147
-
 (2S,3R,4S,5R)-N,3,4-trihydroxy-5-([4-(phenylethynyl)phenyl]ethynyl)tetrahydrofuran-2-carboxamide above, 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
0.0305
-
 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
0.107
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5R)-N,3,4-trihydroxy-5-([4-(phenylethynyl)phenyl]ethynyl)tetrahydrofuran-2-carboxamide
0.2
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5R)-N,3,4-trihydroxy-5-(octa-1,3-diyn-1-yl)tetrahydrofuran-2-carboxamide
0.2
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5R)-N,3,4-trihydroxy-5-(phenylbuta-1,3-diyn-1-yl)tetrahydrofuran-2-carboxamide
0.2
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5S)-N,3,4-trihydroxy-5-(phenylbuta-1,3-diyn-1-yl)tetrahydrofuran-2-carboxamide
0.2
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5S)-N,3,4-trihydroxy-5-([4-(phenylethynyl)phenyl]ethynyl)tetrahydrofuran-2-carboxamide
0.2
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5R)-N,3,4-trihydroxy-5-[2-(4-(2-[4-(trifluoromethyl)phenyl]ethynyl)phenyl)ethynyl]tetrahydrofuran-2-carboxamide
0.2
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5S)-N,3,4-trihydroxy-5-[(4-([4-(trifluoromethyl)phenyl]ethynyl)phenyl)ethynyl]tetrahydrofuran-2-carboxamide
0.2
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5R)-N,3,4-trihydroxy-5-(2-(4-[2-(4-methoxyphenyl)ethynyl]phenyl)ethynyl)tetrahydrofuran-2-carboxamide
0.2
-
 above, pH 6.0, 37°C Escherichia coli (2S,3R,4S,5S)-N,3,4-trihydroxy-5-((4-[(4-methoxyphenyl)ethynyl]phenyl)ethynyl)tetrahydrofuran-2-carboxamide

General Information

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