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Literature summary for 3.5.1.108 extracted from

  • Murphy-Benenato, K.; Olivier, N.; Choy, A.; Ross, P.; Miller, M.; Thresher, J.; Gao, N.; Hale, M.
    Synthesis, structure, and SAR of tetrahydropyran-based LpxC inhibitors (2014), ACS Med. Chem. Lett., 5, 1213-1218A.
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

Crystallization (Comment) Organism
Aquifex aeolicus LpxC with bound UDP-3-O-(acyl)-glucosamine and with 2 and 9, X-ray diffraction structure determination and analysis. Cocrystal structure of Aquifex aeolicus LpxC with bound product UDP-3-O-(acyl)-glucosamine and Pseudomonas aeruginosa with bound 27b docking model, overview Aquifex aeolicus
X-ray diffraction structure determination and analysis Pseudomonas aeruginosa

Inhibitors

Inhibitors Comment Organism Structure
4-({4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]phenoxy}methyl)-N-hydroxyoxane-4-carboxamide
-
Aquifex aeolicus
4-({4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]phenoxy}methyl)-N-hydroxyoxane-4-carboxamide
-
Escherichia coli
4-({4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]phenoxy}methyl)-N-hydroxyoxane-4-carboxamide
-
Pseudomonas aeruginosa
4-({4-[(4-{[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl}phenyl)ethynyl]phenoxy}methyl)-N-hydroxyoxane-4-carboxamide
-
Aquifex aeolicus
4-({4-[(4-{[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl}phenyl)ethynyl]phenoxy}methyl)-N-hydroxyoxane-4-carboxamide
-
Escherichia coli
4-({4-[(4-{[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl}phenyl)ethynyl]phenoxy}methyl)-N-hydroxyoxane-4-carboxamide
-
Pseudomonas aeruginosa
4-({[4-(4-chlorophenoxy)phenyl]sulfanyl}methyl)-N-hydroxyoxane-4-carboxamide
-
Aquifex aeolicus
4-({[4-(4-chlorophenoxy)phenyl]sulfanyl}methyl)-N-hydroxyoxane-4-carboxamide
-
Escherichia coli
4-({[4-(4-chlorophenoxy)phenyl]sulfanyl}methyl)-N-hydroxyoxane-4-carboxamide
-
Pseudomonas aeruginosa
4-[(4-{2-[(dimethylamino)methyl]morpholin-4-yl}phenoxy)methyl]-N-hydroxyoxane-4-carboxamide
-
Aquifex aeolicus
4-[(4-{2-[(dimethylamino)methyl]morpholin-4-yl}phenoxy)methyl]-N-hydroxyoxane-4-carboxamide
-
Escherichia coli
4-[(4-{2-[(dimethylamino)methyl]morpholin-4-yl}phenoxy)methyl]-N-hydroxyoxane-4-carboxamide
-
Pseudomonas aeruginosa
4-[(4-{[4-({2-[(dimethylamino)methyl]morpholin-4-yl}methyl)phenyl]ethynyl}phenoxy)methyl]-N-hydroxyoxane-4-carboxamide
-
Aquifex aeolicus
4-[(4-{[4-({2-[(dimethylamino)methyl]morpholin-4-yl}methyl)phenyl]ethynyl}phenoxy)methyl]-N-hydroxyoxane-4-carboxamide
-
Escherichia coli
4-[(4-{[4-({2-[(dimethylamino)methyl]morpholin-4-yl}methyl)phenyl]ethynyl}phenoxy)methyl]-N-hydroxyoxane-4-carboxamide
-
Pseudomonas aeruginosa
4-{[4-(4-acetylpiperazin-1-yl)phenoxy]methyl}-N-hydroxyoxane-4-carboxamide
-
Aquifex aeolicus
4-{[4-(4-acetylpiperazin-1-yl)phenoxy]methyl}-N-hydroxyoxane-4-carboxamide
-
Escherichia coli
4-{[4-(4-acetylpiperazin-1-yl)phenoxy]methyl}-N-hydroxyoxane-4-carboxamide
-
Pseudomonas aeruginosa
4-{[4-({4-[(4-acetylpiperazin-1-yl)methyl]phenyl}ethynyl)phenoxy]methyl}-N-hydroxyoxane-4-carboxamide
-
Aquifex aeolicus
4-{[4-({4-[(4-acetylpiperazin-1-yl)methyl]phenyl}ethynyl)phenoxy]methyl}-N-hydroxyoxane-4-carboxamide
-
Escherichia coli
4-{[4-({4-[(4-acetylpiperazin-1-yl)methyl]phenyl}ethynyl)phenoxy]methyl}-N-hydroxyoxane-4-carboxamide
-
Pseudomonas aeruginosa
additional information synthesis, structure, structure-activity relationship, and inhibitory potencies of tetrahydropyran-based LpxC inhibitors, overview Aquifex aeolicus
additional information synthesis, structure, structure-activity relationship, and inhibitory potencies of tetrahydropyran-based LpxC inhibitors, overview Escherichia coli
additional information synthesis, structure, structure-activity relationship, and inhibitory potencies of tetrahydropyran-based LpxC inhibitors, overview Pseudomonas aeruginosa
N,4-dihydroxy-1-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenoxy]methyl}cyclohexane-1-carboxamide
-
Aquifex aeolicus
N,4-dihydroxy-1-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenoxy]methyl}cyclohexane-1-carboxamide
-
Escherichia coli
N,4-dihydroxy-1-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenoxy]methyl}cyclohexane-1-carboxamide
-
Pseudomonas aeruginosa
N-hydroxy-4-({4-[(4-{[4-(propan-2-yl)piperazin-1-yl]methyl}phenyl)ethynyl]phenoxy}methyl)oxane-4-carboxamide
-
Aquifex aeolicus
N-hydroxy-4-({4-[(4-{[4-(propan-2-yl)piperazin-1-yl]methyl}phenyl)ethynyl]phenoxy}methyl)oxane-4-carboxamide
-
Escherichia coli
N-hydroxy-4-({4-[(4-{[4-(propan-2-yl)piperazin-1-yl]methyl}phenyl)ethynyl]phenoxy}methyl)oxane-4-carboxamide
-
Pseudomonas aeruginosa
N-hydroxy-4-({4-[4-(propan-2-yl)piperazin-1-yl]phenoxy}methyl)oxane-4-carboxamide
-
Aquifex aeolicus
N-hydroxy-4-({4-[4-(propan-2-yl)piperazin-1-yl]phenoxy}methyl)oxane-4-carboxamide
-
Escherichia coli
N-hydroxy-4-({4-[4-(propan-2-yl)piperazin-1-yl]phenoxy}methyl)oxane-4-carboxamide
-
Pseudomonas aeruginosa
N-hydroxy-4-({[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenyl]sulfanyl}methyl)oxane-4-carboxamide
-
Aquifex aeolicus
N-hydroxy-4-({[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenyl]sulfanyl}methyl)oxane-4-carboxamide
-
Escherichia coli
N-hydroxy-4-({[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenyl]sulfanyl}methyl)oxane-4-carboxamide
-
Pseudomonas aeruginosa
N-hydroxy-4-methoxy-1-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenoxy]methyl}cyclohexane-1-carboxamide
-
Aquifex aeolicus
N-hydroxy-4-methoxy-1-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenoxy]methyl}cyclohexane-1-carboxamide
-
Escherichia coli
N-hydroxy-4-methoxy-1-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenoxy]methyl}cyclohexane-1-carboxamide
-
Pseudomonas aeruginosa
N-hydroxy-4-[(4-{4-[2-(morpholin-4-yl)ethyl]piperazin-1-yl}phenoxy)methyl]oxane-4-carboxamide
-
Aquifex aeolicus
N-hydroxy-4-[(4-{4-[2-(morpholin-4-yl)ethyl]piperazin-1-yl}phenoxy)methyl]oxane-4-carboxamide
-
Escherichia coli
N-hydroxy-4-[(4-{4-[2-(morpholin-4-yl)ethyl]piperazin-1-yl}phenoxy)methyl]oxane-4-carboxamide
-
Pseudomonas aeruginosa
N-hydroxy-4-[(4-{[4-({4-[2-(1H-imidazol-1-yl)ethyl]piperazin-1-yl}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
-
Aquifex aeolicus
N-hydroxy-4-[(4-{[4-({4-[2-(1H-imidazol-1-yl)ethyl]piperazin-1-yl}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
-
Escherichia coli
N-hydroxy-4-[(4-{[4-({4-[2-(1H-imidazol-1-yl)ethyl]piperazin-1-yl}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
-
Pseudomonas aeruginosa
N-hydroxy-4-[(4-{[4-({4-[2-(morpholin-4-yl)-2-oxoethyl]piperazin-1-yl}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
-
Aquifex aeolicus
N-hydroxy-4-[(4-{[4-({4-[2-(morpholin-4-yl)-2-oxoethyl]piperazin-1-yl}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
-
Escherichia coli
N-hydroxy-4-[(4-{[4-({4-[2-(morpholin-4-yl)-2-oxoethyl]piperazin-1-yl}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
-
Pseudomonas aeruginosa
N-hydroxy-4-[(4-{[4-({4-[2-(morpholin-4-yl)ethyl]piperazin-1-yl}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
-
Aquifex aeolicus
N-hydroxy-4-[(4-{[4-({4-[2-(morpholin-4-yl)ethyl]piperazin-1-yl}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
-
Escherichia coli
N-hydroxy-4-[(4-{[4-({4-[2-(morpholin-4-yl)ethyl]piperazin-1-yl}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
-
Pseudomonas aeruginosa
N-hydroxy-4-[(4-{[4-({[(4-methoxyphenyl)methyl]amino}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
-
Aquifex aeolicus
N-hydroxy-4-[(4-{[4-({[(4-methoxyphenyl)methyl]amino}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
-
Escherichia coli
N-hydroxy-4-[(4-{[4-({[(4-methoxyphenyl)methyl]amino}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
-
Pseudomonas aeruginosa
N-hydroxy-4-{[4-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}ethynyl)phenoxy]methyl}oxane-4-carboxamide
-
Aquifex aeolicus
N-hydroxy-4-{[4-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}ethynyl)phenoxy]methyl}oxane-4-carboxamide
-
Escherichia coli
N-hydroxy-4-{[4-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}ethynyl)phenoxy]methyl}oxane-4-carboxamide
-
Pseudomonas aeruginosa
N-hydroxy-4-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)benzene-1-sulfinyl]methyl}oxane-4-carboxamide
-
Aquifex aeolicus
N-hydroxy-4-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)benzene-1-sulfinyl]methyl}oxane-4-carboxamide
-
Escherichia coli
N-hydroxy-4-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)benzene-1-sulfinyl]methyl}oxane-4-carboxamide
-
Pseudomonas aeruginosa
N-hydroxy-4-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenoxy]methyl}oxane-4-carboxamide
-
Aquifex aeolicus
N-hydroxy-4-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenoxy]methyl}oxane-4-carboxamide
-
Escherichia coli
N-hydroxy-4-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenoxy]methyl}oxane-4-carboxamide
-
Pseudomonas aeruginosa
N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)benzamide
-
Aquifex aeolicus
N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)benzamide
-
Escherichia coli
N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)benzamide
-
Pseudomonas aeruginosa
RS-130830
-
Aquifex aeolicus
RS-130830
-
Escherichia coli
RS-130830
-
Pseudomonas aeruginosa

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
-
r
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine + H2O Pseudomonas aeruginosa
-
UDP-3-O-[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + acetate
-
r
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine + H2O Aquifex aeolicus
-
UDP-3-O-[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + acetate
-
r
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine + H2O Escherichia coli W3110 / ATCC 27325
-
UDP-3-O-[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + acetate
-
r

Organism

Organism UniProt Comment Textmining
Aquifex aeolicus O67648 gene lpxC
-
Escherichia coli
-
gene lpxC
-
Escherichia coli W3110 / ATCC 27325
-
gene lpxC
-
Pseudomonas aeruginosa
-
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
-
r
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine + H2O
-
Pseudomonas aeruginosa UDP-3-O-[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + acetate
-
r
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine + H2O
-
Aquifex aeolicus UDP-3-O-[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + acetate
-
r
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine + H2O
-
Aquifex aeolicus UDP-3-O-[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + acetate the product diphosphate group covalently links to the glucosamine directly interacted with Lys227 and a protein loop between beta6' and alpha2' of domain II r
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine + H2O
-
Escherichia coli W3110 / ATCC 27325 UDP-3-O-[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + acetate
-
r

Synonyms

Synonyms Comment Organism
LpxC
-
Escherichia coli
LpxC
-
Pseudomonas aeruginosa
LpxC
-
Aquifex aeolicus
UDP-3-O-(acyl)-N-acetylglucosamine deacetylase
-
Escherichia coli
UDP-3-O-(acyl)-N-acetylglucosamine deacetylase
-
Pseudomonas aeruginosa
UDP-3-O-(acyl)-N-acetylglucosamine deacetylase
-
Aquifex aeolicus

General Information

General Information Comment Organism
additional information cocrystal structure of Aquifex aeolicus LpxC with bound UDP-3-O-(acyl)-glucosamine and Pseudomonas aeruginosa with bound 27b docking model, overview Pseudomonas aeruginosa
additional information cocrystal structure of Aquifex aeolicus LpxC with bound UDP-3-O-(acyl)-glucosamine and Pseudomonas. aeruginosa with bound 27b docking model, overview Aquifex aeolicus