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Literature summary for 4.1.99.5 extracted from

  • Das, D.; Ellington, B.; Paul, B.; Marsh, E.N.
    Mechanistic insights from reaction of alpha-oxiranyl-aldehydes with cyanobacterial aldehyde deformylating oxygenase (2014), ACS Chem. Biol., 9, 570-577.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 4.1.99.5

Cloned(Commentary)

Cloned (Comment) Organism
recombinant expression in Escherichia coli Nostoc punctiforme

Inhibitors

Inhibitors Comment Organism Structure
additional information trans-3-nonyloxirane-2-carbaldehyde and trans-3-pentadecanyloxirane-2-carbaldehyde are no inhibitors of the enzyme Nostoc punctiforme

Metals/Ions

Metals/Ions Comment Organism Structure
Fe2+ dependent on Nostoc punctiforme

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
long-chain aldehyde + O2 + 2 NADPH + 2 H+ Nostoc punctiforme
-
 alkane + formate + H2O + 2 NADP+
-
 ?

Organism

Organism UniProt Comment Textmining
Nostoc punctiforme
-
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant enzyme from Escherichia coli Nostoc punctiforme

Reaction

Reaction Comment Organism Reaction ID
octadecanal + O2 + 2 NADPH + 2 H+ = heptadecane + formate + H2O + 2 NADP+ proposed mechanism of cADO involving homolytic cleavage of the C1-C2 bond of aldehyde by di-iron peroxo species, and proposed mechanism for deformylation involving heterolytic cleavage of the C1-C2 bond Nostoc punctiforme
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
dodecanal + O2 + 2 NADH + 2 H+ with reducing system NADH/phenazine methosulfate Nostoc punctiforme undecane + formate + H2O + 2 NAD+
-
 ?
long-chain aldehyde + O2 + 2 NADPH + 2 H+
-
 Nostoc punctiforme alkane + formate + H2O + 2 NADP+
-
 ?
additional information the enzyme is more active with either long-chain (C18-C14) or short-chain (C9-C5) aldehydes whereas medium chain aldehydes, including dodecanal, are turned over considerably more slowly Nostoc punctiforme ?
-
 ?
octadecanal + O2 + 2 NADH + 2 H+ with reducing system NADH/phenazine methosulfate Nostoc punctiforme heptadecane + formate + H2O + 2 NAD+
-
 ?
trans-3-nonyloxirane-2-carbaldehyde + 2 NADH + 2 H+ with reducing system NADH/phenazine methosulfate Nostoc punctiforme 2-nonyloxirane + formate + H2O + 2 NAD+
-
 ?
trans-3-pentadecanyloxirane-2-carbaldehyde + 2 NADH + O2 + 2 H+ with reducing system NADH/phenazine methosulfate Nostoc punctiforme 2-pentadecanyloxirane + formate + 2 NAD+ + H2O
-
 ?

Synonyms

Synonyms Comment Organism
aldehyde deformylating oxygenase
-
 Nostoc punctiforme
cADO
-
 Nostoc punctiforme
cyanobacterial aldehyde decarbonylase
-
 Nostoc punctiforme

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Nostoc punctiforme

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.00027
-
 trans-3-nonyloxirane-2-carbaldehyde pH 7.2, 37°C Nostoc punctiforme
0.00048
-
 trans-3-pentadecanyloxirane-2-carbaldehyde pH 7.2, 37°C Nostoc punctiforme
0.0018
-
 octadecanal pH 7.2, 37°C Nostoc punctiforme

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.2
-
 assay at Nostoc punctiforme

Cofactor

Cofactor Comment Organism Structure
NADH
-
 Nostoc punctiforme
NADPH physiological cofactor Nostoc punctiforme

General Information

General Information Comment Organism
metabolism in cyanobacteria, aldehyde deformylating oxygenase catalyzes the decarbonylation of fatty aldehydes to the corresponding alkanes or alkenes, last step in the biosynthesis of long-chain aliphatic hydrocarbons, which are derived from fatty acids Nostoc punctiforme