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Literature summary for 1.3.1.9 extracted from

  • Neckles, C.; Pschibul, A.; Lai, C.T.; Hirschbeck, M.; Kuper, J.; Davoodi, S.; Zou, J.; Liu, N.; Pan, P.; Shah, S.; Daryaee, F.; Bommineni, G.R.; Lai, C.; Simmerling, C.; Kisker, C.; Tonge, P.J.
    Selectivity of pyridone- and diphenyl ether-based inhibitors for the Yersinia pestis FabV enoyl-ACP reductase (2016), Biochemistry, 55, 2992-3006.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.3.1.9

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli BL21(DE3) cells Yersinia pestis

Crystallization (Commentary)

Crystallization (Comment) Organism
hanging drop vapor diffusion method, using 150 mM (NH4)2SO4, 100 mM MES (pH 5.6-5.9), and 26.5-37.5% (w/v) PEG4000 Yersinia pestis

Protein Variants

Protein Variants Comment Organism
T267A the mutation results in a reduction in the kcat/KM value compared to the wild type enzyme Yersinia pestis
T267C inactive Yersinia pestis
T267G the mutation results in a 40fold reduction in the kcat/KM value compared to the wild type enzyme Yersinia pestis
T267V the mutation results in a reduction in the kcat/KM value compared to the wild type enzyme Yersinia pestis
T267Y the mutation results in a reduction in the kcat/KM value compared to the wild type enzyme Yersinia pestis
T276S the mutation shows wild type catalytic efficiency but significantly reduces the affinity of diphenyl ether inhibitors for the enzyme (from 20fold to up to 100fold) Yersinia pestis

Inhibitors

Inhibitors Comment Organism Structure
1-benzyl-4-decylpyridin-2(1H)-one
-
 Yersinia pestis
1-[(2-chlorophenyl)methyl]-4-decylpyridin-2(1H)-one
-
 Yersinia pestis
1-[(3-amino-2-methylphenyl)methyl]-4-decylpyridin-2(1H)-one
-
 Yersinia pestis
2-(2-aminophenoxy)-5-decylphenol
-
 Yersinia pestis
2-(2-chlorophenoxy)-5-decylphenol
-
 Yersinia pestis
2-(4-aminophenoxy)-5-decylphenol
-
 Yersinia pestis
2-decyl-1-methyl-5-(2-methylphenoxy)pyridin-4(1H)-one
-
 Yersinia pestis
2-decyl-1-methyl-5-(4-nitrophenoxy)pyridin-4(1H)-one competitive inhibition Yersinia pestis
2-phenoxy-5-tetradecylphenol
-
 Yersinia pestis
4-decyl-1-[(2-methylphenyl)methyl]pyridin-2(1H)-one
-
 Yersinia pestis
4-decyl-1-[(4-nitrophenyl)methyl]pyridin-2(1H)-one noncompetitive inhibition Yersinia pestis
5-(4-amino-2-methylphenoxy)-2-decyl-1-methylpyridin-4(1H)-one
-
 Yersinia pestis
5-(4-aminophenoxy)-2-decyl-1-methylpyridin-4(1H)-one
-
 Yersinia pestis
5-butyl-2-phenoxyphenol
-
 Yersinia pestis
5-decyl-2-(2-fluorophenoxy)phenol
-
 Yersinia pestis
5-decyl-2-(2-methylphenoxy)phenol
-
 Yersinia pestis
5-decyl-2-(2-nitrophenoxy)phenol
-
 Yersinia pestis
5-decyl-2-(4-nitrophenoxy)phenol uncompetitive inhibition Yersinia pestis
5-decyl-2-phenoxyphenol
-
 Yersinia pestis
5-ethyl-2-phenoxyphenol
-
 Yersinia pestis
5-octyl-2-phenoxyphenol
-
 Yersinia pestis
NADH
-
 Yersinia pestis
triclosan poor inhibitor Yersinia pestis

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.006
-
 trans-2-octenoyl-[acyl-carrier protein] wild type enzyme, at pH 8.0 and 30°C Yersinia pestis
0.007
-
 trans-2-octenoyl-CoA wild type enzyme, at pH 8.0 and 30°C Yersinia pestis
0.01
-
 NADH wild type enzyme, at pH 8.0 and 30°C Yersinia pestis
0.012
-
 trans-2-dodecenoyl-CoA mutant enzyme T267W, at pH 8.0 and 30°C Yersinia pestis
0.014
-
 trans-2-dodecenoyl-CoA wild type enzyme, at pH 8.0 and 30°C Yersinia pestis
0.015
-
 trans-2-dodecenoyl-CoA mutant enzyme T267Y, at pH 8.0 and 30°C Yersinia pestis
0.017
-
 trans-2-dodecenoyl-CoA mutant enzyme T267V, at pH 8.0 and 30°C Yersinia pestis
0.018
-
 trans-2-dodecenoyl-CoA mutant enzyme T267S, at pH 8.0 and 30°C Yersinia pestis
0.023
-
 trans-2-decenoyl-CoA wild type enzyme, at pH 8.0 and 30°C Yersinia pestis
0.038
-
 trans-2-dodecenoyl-CoA mutant enzyme T267G, at pH 8.0 and 30°C Yersinia pestis
0.053
-
 trans-2-dodecenoyl-CoA mutant enzyme T267A, at pH 8.0 and 30°C Yersinia pestis

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
an acyl-[acyl-carrier protein] + NAD+ Yersinia pestis
-
 a trans-2,3-dehydroacyl-[acyl-carrier protein] + NADH + H+
-
 ?
an acyl-[acyl-carrier protein] + NAD+ Yersinia pestis A1122
-
 a trans-2,3-dehydroacyl-[acyl-carrier protein] + NADH + H+
-
 ?

Organism

Organism UniProt Comment Textmining
Yersinia pestis Q8Z9U1
-
-
Yersinia pestis A1122 Q8Z9U1
-
-

Purification (Commentary)

Purification (Comment) Organism
His-bind Ni2+-NTA resin column chromatography Yersinia pestis

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
an acyl-[acyl-carrier protein] + NAD+
-
 Yersinia pestis a trans-2,3-dehydroacyl-[acyl-carrier protein] + NADH + H+
-
 ?
an acyl-[acyl-carrier protein] + NAD+
-
 Yersinia pestis A1122 a trans-2,3-dehydroacyl-[acyl-carrier protein] + NADH + H+
-
 ?
trans-2-decenoyl-CoA + NADH + H+
-
 Yersinia pestis ?
-
 ?
trans-2-decenoyl-CoA + NADH + H+
-
 Yersinia pestis A1122 ?
-
 ?
trans-2-dodecenoyl-CoA + NADH + H+
-
 Yersinia pestis ?
-
 ?
trans-2-dodecenoyl-CoA + NADH + H+
-
 Yersinia pestis A1122 ?
-
 ?
trans-2-octenoyl-CoA + NADH + H+
-
 Yersinia pestis ?
-
 ?
trans-2-octenoyl-CoA + NADH + H+
-
 Yersinia pestis A1122 ?
-
 ?
trans-2-octenoyl-[acyl-carrier protein] + NADH + H+
-
 Yersinia pestis ?
-
 ?
trans-2-octenoyl-[acyl-carrier protein] + NADH + H+
-
 Yersinia pestis A1122 ?
-
 ?

Synonyms

Synonyms Comment Organism
enoyl-ACP reductase
-
 Yersinia pestis
enoyl-acyl carrier protein reductase
-
 Yersinia pestis
FabV
-
 Yersinia pestis

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.08
-
 trans-2-dodecenoyl-CoA mutant enzyme T267Y, at pH 8.0 and 30°C Yersinia pestis
0.25
-
 trans-2-dodecenoyl-CoA mutant enzyme T267V, at pH 8.0 and 30°C Yersinia pestis
0.27
-
 trans-2-octenoyl-CoA wild type enzyme, at pH 8.0 and 30°C Yersinia pestis
2.2
-
 trans-2-dodecenoyl-CoA mutant enzyme T267A, at pH 8.0 and 30°C Yersinia pestis
5.53
-
 trans-2-decenoyl-CoA wild type enzyme, at pH 8.0 and 30°C Yersinia pestis
6
-
 trans-2-dodecenoyl-CoA mutant enzyme T267G, at pH 8.0 and 30°C Yersinia pestis
14.92
-
 trans-2-octenoyl-[acyl-carrier protein] wild type enzyme, at pH 8.0 and 30°C Yersinia pestis
64.4
-
 trans-2-dodecenoyl-CoA mutant enzyme T267W, at pH 8.0 and 30°C Yersinia pestis
83.9
-
 trans-2-dodecenoyl-CoA mutant enzyme T267S, at pH 8.0 and 30°C Yersinia pestis
91.13
-
 trans-2-dodecenoyl-CoA wild type enzyme, at pH 8.0 and 30°C Yersinia pestis

Cofactor

Cofactor Comment Organism Structure
NAD+
-
 Yersinia pestis
NADH
-
 Yersinia pestis

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0001
-
 5-decyl-2-(4-nitrophenoxy)phenol wild type enzyme, at pH 8.0 and 30°C Yersinia pestis
0.0002
-
 2-decyl-1-methyl-5-(4-nitrophenoxy)pyridin-4(1H)-one IC50 above 0.05 mM, wild type enzyme, at pH 8.0 and 30°C Yersinia pestis
0.008
-
 4-decyl-1-[(4-nitrophenyl)methyl]pyridin-2(1H)-one wild type enzyme, at pH 8.0 and 30°C Yersinia pestis
0.022
-
 NADH wild type enzyme, at pH 8.0 and 30°C Yersinia pestis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0001
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 5-decyl-2-(2-fluorophenoxy)phenol
0.0002
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 5-butyl-2-phenoxyphenol
0.0002
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 5-decyl-2-(4-nitrophenoxy)phenol
0.0002
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 5-(4-aminophenoxy)-2-decyl-1-methylpyridin-4(1H)-one
0.0003
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 2-decyl-1-methyl-5-(2-methylphenoxy)pyridin-4(1H)-one
0.001
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 5-octyl-2-phenoxyphenol
0.001
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 5-decyl-2-(2-nitrophenoxy)phenol
0.002
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 2-phenoxy-5-tetradecylphenol
0.002
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 2-(2-aminophenoxy)-5-decylphenol
0.003
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 5-decyl-2-phenoxyphenol
0.003
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 2-(4-aminophenoxy)-5-decylphenol
0.003
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 5-decyl-2-(2-methylphenoxy)phenol
0.004
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 2-(2-chlorophenoxy)-5-decylphenol
0.02
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 5-ethyl-2-phenoxyphenol
0.021
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 4-decyl-1-[(4-nitrophenyl)methyl]pyridin-2(1H)-one
0.03
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 5-(4-amino-2-methylphenoxy)-2-decyl-1-methylpyridin-4(1H)-one
0.042
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 1-benzyl-4-decylpyridin-2(1H)-one
0.05
-
 IC50 above 0.05 mM, wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 2-decyl-1-methyl-5-(4-nitrophenoxy)pyridin-4(1H)-one
0.055
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 1-[(2-chlorophenyl)methyl]-4-decylpyridin-2(1H)-one
0.056
-
 wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 4-decyl-1-[(2-methylphenyl)methyl]pyridin-2(1H)-one
0.1
-
 IC50 above 0.1 mM, wild type enzyme, at pH 8.0 and 30°C Yersinia pestis 1-[(3-amino-2-methylphenyl)methyl]-4-decylpyridin-2(1H)-one

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
5
-
 trans-2-dodecenoyl-CoA mutant enzyme T267Y, at pH 8.0 and 30°C Yersinia pestis
17
-
 trans-2-dodecenoyl-CoA mutant enzyme T267A, at pH 8.0 and 30°C Yersinia pestis
17
-
 trans-2-dodecenoyl-CoA mutant enzyme T267V, at pH 8.0 and 30°C Yersinia pestis
33
-
 trans-2-octenoyl-CoA wild type enzyme, at pH 8.0 and 30°C Yersinia pestis
167
-
 trans-2-dodecenoyl-CoA mutant enzyme T267G, at pH 8.0 and 30°C Yersinia pestis
233
-
 trans-2-decenoyl-CoA wild type enzyme, at pH 8.0 and 30°C Yersinia pestis
2500
-
 trans-2-octenoyl-[acyl-carrier protein] wild type enzyme, at pH 8.0 and 30°C Yersinia pestis
4667
-
 trans-2-dodecenoyl-CoA mutant enzyme T267S, at pH 8.0 and 30°C Yersinia pestis
5817
-
 trans-2-dodecenoyl-CoA mutant enzyme T267W, at pH 8.0 and 30°C Yersinia pestis
6500
-
 trans-2-dodecenoyl-CoA wild type enzyme, at pH 8.0 and 30°C Yersinia pestis