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Literature summary for 1.5.1.B7 extracted from

  • McFarlane, J.S.; Davis, C.L.; Lamb, A.L.
    Staphylopine, pseudopaline, and yersinopine dehydrogenases A structural and kinetic analysis of a new functional class of opine dehydrogenase (2018), J. Biol. Chem., 293, 8009-8019 .
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

Crystallization (Comment) Organism
purified recombinant wild-type PaODH complexed with NADP+, X-ray diffraction structure determination and analysis, single wavelength anomalous dispersion, at 1.95 A resolution, molecular replacement and modelling Pseudomonas aeruginosa

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
additional information steady-state kinetic analysis, overview Pseudomonas aeruginosa
14
-
2-oxoglutarate recombinant enzyme, with NADPH and L-histidine nicotianamine, pH 8.0, 22┬░C Pseudomonas aeruginosa
61
-
2-oxoglutarate recombinant enzyme, with NADH and L-histidine nicotianamine, pH 8.0, 22┬░C Pseudomonas aeruginosa

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+ Pseudomonas aeruginosa
-
pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+ Pseudomonas aeruginosa ATCC 15692
-
pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+ Pseudomonas aeruginosa 1C
-
pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+ Pseudomonas aeruginosa PRS 101
-
pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+ Pseudomonas aeruginosa DSM 22644
-
pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+ Pseudomonas aeruginosa CIP 104116
-
pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+ Pseudomonas aeruginosa LMG 12228
-
pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+ Pseudomonas aeruginosa JCM 14847
-
pseudopaline + NADP+ + H2O
-
?

Organism

Organism UniProt Comment Textmining
Pseudomonas aeruginosa Q9HUX5
-
-
Pseudomonas aeruginosa 1C Q9HUX5
-
-
Pseudomonas aeruginosa ATCC 15692 Q9HUX5
-
-
Pseudomonas aeruginosa CIP 104116 Q9HUX5
-
-
Pseudomonas aeruginosa DSM 22644 Q9HUX5
-
-
Pseudomonas aeruginosa JCM 14847 Q9HUX5
-
-
Pseudomonas aeruginosa LMG 12228 Q9HUX5
-
-
Pseudomonas aeruginosa PRS 101 Q9HUX5
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+
-
Pseudomonas aeruginosa pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+
-
Pseudomonas aeruginosa ATCC 15692 pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+
-
Pseudomonas aeruginosa 1C pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+
-
Pseudomonas aeruginosa PRS 101 pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+
-
Pseudomonas aeruginosa DSM 22644 pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+
-
Pseudomonas aeruginosa CIP 104116 pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+
-
Pseudomonas aeruginosa LMG 12228 pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + 2-oxoglutarate + NADPH + H+
-
Pseudomonas aeruginosa JCM 14847 pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa pseudopaline + NAD+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa ATCC 15692 pseudopaline + NAD+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa 1C pseudopaline + NAD+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa PRS 101 pseudopaline + NAD+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa DSM 22644 pseudopaline + NAD+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa CIP 104116 pseudopaline + NAD+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa LMG 12228 pseudopaline + NAD+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa JCM 14847 pseudopaline + NAD+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADPH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADPH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa ATCC 15692 pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADPH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa 1C pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADPH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa PRS 101 pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADPH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa DSM 22644 pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADPH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa CIP 104116 pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADPH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa LMG 12228 pseudopaline + NADP+ + H2O
-
?
(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + oxaloacetate + NADPH + H+ i.e. N-[(3S)-3-amino-3-carboxypropyl]-L-histidine Pseudomonas aeruginosa JCM 14847 pseudopaline + NADP+ + H2O
-
?
additional information L-histidine nicotianamine is preferred over D-histidine nicotianamine, poor activity with D-histidine nicotianamine Pseudomonas aeruginosa ?
-
-
additional information L-histidine nicotianamine is preferred over D-histidine nicotianamine, poor activity with D-histidine nicotianamine Pseudomonas aeruginosa ATCC 15692 ?
-
-
additional information L-histidine nicotianamine is preferred over D-histidine nicotianamine, poor activity with D-histidine nicotianamine Pseudomonas aeruginosa 1C ?
-
-
additional information L-histidine nicotianamine is preferred over D-histidine nicotianamine, poor activity with D-histidine nicotianamine Pseudomonas aeruginosa PRS 101 ?
-
-
additional information L-histidine nicotianamine is preferred over D-histidine nicotianamine, poor activity with D-histidine nicotianamine Pseudomonas aeruginosa DSM 22644 ?
-
-
additional information L-histidine nicotianamine is preferred over D-histidine nicotianamine, poor activity with D-histidine nicotianamine Pseudomonas aeruginosa CIP 104116 ?
-
-
additional information L-histidine nicotianamine is preferred over D-histidine nicotianamine, poor activity with D-histidine nicotianamine Pseudomonas aeruginosa LMG 12228 ?
-
-
additional information L-histidine nicotianamine is preferred over D-histidine nicotianamine, poor activity with D-histidine nicotianamine Pseudomonas aeruginosa JCM 14847 ?
-
-

Synonyms

Synonyms Comment Organism
cntM
-
Pseudomonas aeruginosa
ODH
-
Pseudomonas aeruginosa
PA4835
-
Pseudomonas aeruginosa
PaODH
-
Pseudomonas aeruginosa
pseudopaline synthase
-
Pseudomonas aeruginosa

Temperature Optimum [┬░C]

Temperature Optimum [┬░C] Temperature Optimum Maximum [┬░C] Comment Organism
22
-
assay at Pseudomonas aeruginosa

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.33
-
NADPH recombinant enzyme, with 2-oxoglutarate and L-histidine nicotianamine, pH 8.0, 22┬░C Pseudomonas aeruginosa
0.42
-
2-oxoglutarate recombinant enzyme, with NADPH and L-histidine nicotianamine, pH 8.0, 22┬░C Pseudomonas aeruginosa
0.71
-
NADH recombinant enzyme, with 2-oxoglutarate and L-histidine nicotianamine, pH 8.0, 22┬░C Pseudomonas aeruginosa
0.92
-
2-oxoglutarate recombinant enzyme, with NADH and L-histidine nicotianamine, pH 8.0, 22┬░C Pseudomonas aeruginosa

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
assay at Pseudomonas aeruginosa

Cofactor

Cofactor Comment Organism Structure
additional information significant catalysis is also observed for PaODH with NADH, the kcat of PaODH is 2.2fold higher than the kcat for NADPH. PaODH is nonspecific for the NAD(P)H substrate Pseudomonas aeruginosa
NADH
-
Pseudomonas aeruginosa
NADP+ binding structure, overview Pseudomonas aeruginosa
NADPH
-
Pseudomonas aeruginosa

General Information

General Information Comment Organism
metabolism opine dehydrogenases (ODHs) from the bacterial pathogens, e.g. Staphylococcus aureus, Pseudomonas aeruginosa, and Yersinia pestis, perform the final enzymatic step in the biosynthesis of the class of opine metallophores, which includes staphylopine, pseudopaline, and yersinopine, respectively. Comparison of structure-function relationships, overview Pseudomonas aeruginosa
additional information structure-function analysis, stereochemic reaction, overview. Active site structure involving Asp153 and substrate binding analysis. The histidine is positioned to act as a general acid/general base deprotonating the nucleophile and then donating the proton back to the 2-carbon hydroxyl leading to water release and Schiff base formation. HisNA is oriented with the imidazole moiety deep in the active site to confer stereoselectivity. This places the primary amine of the aminobutyrate proximal to the plane between the hydride and His242, positioning the substrate for nucleophilic attack. The nicotinamide ring hydride is 8.5 A distant from the histidine proton, too far for catalysis, further supporting the necessity of domain closure Pseudomonas aeruginosa
physiological function opine dehydrogenases (ODHs) from the bacterial pathogens, e.g. Staphylococcus aureus, Pseudomonas aeruginosa, and Yersinia pestis, perform the final enzymatic step in the biosynthesis of the class of opine metallophores, which includes staphylopine, pseudopaline, and yersinopine, respectively. Important role for this pathway in metal acquisition and virulence in humans, including in lung and burn-wound infections (Pseudomonas aeruginosa) and in blood and heart infections (Staphylococcus aureus) Pseudomonas aeruginosa

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.015
-
2-oxoglutarate recombinant enzyme, with NADH and L-histidine nicotianamine, pH 8.0, 22┬░C Pseudomonas aeruginosa
0.03
-
2-oxoglutarate recombinant enzyme, with NADPH and L-histidine nicotianamine, pH 8.0, 22┬░C Pseudomonas aeruginosa