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Literature summary for 3.5.1.108 extracted from

  • Clements, J.M.; Coignard, F.; Johnson, I.; Chandler, S.; Palan, S.; Waller, A.; Wijkmans, J.; Hunter, M.G.
    Antibacterial activities and characterization of novel inhibitors of LpxC (2002), Antimicrob. Agents Chemother., 46, 1793-1799.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 3.5.1.108

Protein Variants

Protein Variants Comment Organism
I38T lpxC gene Escherichia coli
additional information Escherichia coli mutants with decreased susceptibility to (R)-2-(4-bromophenylsulfonamido)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxypropanamide are selected Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
(R)-2-(4-bromophenylsulfonamido)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxypropanamide
-
 Escherichia coli
(R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide
-
 Escherichia coli
(S)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine
-
 Escherichia coli
additional information (R)-2-(4-bromophenylsulfonamido)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxypropanamide and (R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide show predominantly gram-negative activities, with activities against members of the Enterobacteriaceae, Serratia marcescens, Morganella morganii, Moraxella catarrhalis, Haemophilus influenzae, and Burkholderia cepacia. Neither compound showed activity against Pseudomonas aeruginosa; however, against a leaky Pseudomonas aeruginosa strain, some activity is seen with (R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide. (R)-2-(4-bromophenylsulfonamido)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxypropanamide and (R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide have little or no activity against the gram-positive bacteria tested Escherichia coli

Metals/Ions

Metals/Ions Comment Organism Structure
additional information metalloenzyme Escherichia coli

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Escherichia coli catalyzes the second step in the biosynthesis of lipid A ?
-
 ?
additional information Escherichia coli D22 catalyzes the second step in the biosynthesis of lipid A ?
-
 ?
UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine + H2O Escherichia coli natural substrate UDP-3-O-((R)-3-hydroxymyristoyl)-D-glucosamine + acetate
-
 ?
UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine + H2O Escherichia coli D22 natural substrate UDP-3-O-((R)-3-hydroxymyristoyl)-D-glucosamine + acetate
-
 ?

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
 D22
-
Escherichia coli D22
-
 D22
-

Purification (Commentary)

Purification (Comment) Organism
-
 Escherichia coli

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information catalyzes the second step in the biosynthesis of lipid A Escherichia coli ?
-
 ?
additional information catalyzes the second step in the biosynthesis of lipid A Escherichia coli D22 ?
-
 ?
UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine + H2O natural substrate Escherichia coli UDP-3-O-((R)-3-hydroxymyristoyl)-D-glucosamine + acetate
-
 ?
UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine + H2O natural substrate Escherichia coli D22 UDP-3-O-((R)-3-hydroxymyristoyl)-D-glucosamine + acetate
-
 ?

Synonyms

Synonyms Comment Organism
LpxC
-
 Escherichia coli
UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase
-
 Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00016
-
-
 Escherichia coli (R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide
0.0004
-
-
 Escherichia coli (R)-2-(4-bromophenylsulfonamido)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxypropanamide
0.00044
-
-
 Escherichia coli (S)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine