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Literature summary for 4.1.99.5 extracted from

  • Warui, D.M.; Li, N.; N?rgaard, H.; Krebs, C.; Bollinger, J.M.; Booker, S.J.
    Detection of formate, rather than carbon monoxide, as the stoichiometric coproduct in conversion of fatty aldehydes to alkanes by a cyanobacterial aldehyde decarbonylase (2011), J. Am. Chem. Soc., 133, 3316-3319.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

Cloned (Comment) Organism
His-tagged version expressed in Escherichia coli Nostoc punctiforme
recombinant overexpression in Escherichia coli Nostoc punctiforme

Metals/Ions

Metals/Ions Comment Organism Structure
Fe2+ a ferritin-like protein with a dinuclear metal cofactor Nostoc punctiforme

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Nostoc punctiforme the aldehyde hydrogen is retained in the HCO2- and the hydrogen in the nascent methyl group of the alkane originates, at least in part, from solvent. The reaction appears to be formally hydrolytic, but the improbability of a hydrolytic mechanism having the primary carbanion as the leaving group, the structural similarity of the aldehyde decarbonylases to other O2-activating non-heme di-iron proteins, and the dependence of in vitro aldehyde decarbonylase activity on the presence of a reducing system implicate some type of redox mechanism. Two possible resolutions to this conundrum, overview ?
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?
octadecanal + O2 + 2 NADPH + 2 H+ Nostoc punctiforme
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heptadecane + formate + H2O + 2 NADP+
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?

Organism

Organism UniProt Comment Textmining
Nostoc punctiforme
-
-
-

Purification (Commentary)

Purification (Comment) Organism
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Nostoc punctiforme

Reaction

Reaction Comment Organism Reaction ID
octadecanal + O2 + 2 NADPH + 2 H+ = heptadecane + formate + H2O + 2 NADP+ possible reaction mechanism, overview. Formate is the coproduct of alkane production by the Np AD, (ii) the aldehyde hydrogen of the substrate is retained in the formate, and (iii) the hydrogen added to C2 derives (at least in part) from solvent Nostoc punctiforme

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information the aldehyde hydrogen is retained in the HCO2- and the hydrogen in the nascent methyl group of the alkane originates, at least in part, from solvent. The reaction appears to be formally hydrolytic, but the improbability of a hydrolytic mechanism having the primary carbanion as the leaving group, the structural similarity of the aldehyde decarbonylases to other O2-activating non-heme di-iron proteins, and the dependence of in vitro aldehyde decarbonylase activity on the presence of a reducing system implicate some type of redox mechanism. Two possible resolutions to this conundrum, overview Nostoc punctiforme ?
-
?
octadecanal + NADPH + O2 activity depends on the presence of a reducing system (NADPH, ferredoxin and ferredoxin reductase) Nostoc punctiforme heptadecane + formate + H2O + NADP+
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?
octadecanal + O2 + 2 NADPH + 2 H+
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Nostoc punctiforme heptadecane + formate + H2O + 2 NADP+
-
?
octadecanal + O2 + 2 NADPH + 2 H+ the in vitro activity of the enzyme depends on the presence of a reducing system, i.e. NADPH, ferredoxin, and ferredoxin reductase Nostoc punctiforme heptadecane + formate + H2O + 2 NADP+
-
?

Synonyms

Synonyms Comment Organism
aldehyde decarbonylase
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Nostoc punctiforme
More the cyanobacterial aldehyde decarbonylases belong to the family of alpha-helical ferritin-like proteins that harbor carboxylate-bridged dimetal (most often diiron) cofactors Nostoc punctiforme

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
22
-
assay at Nostoc punctiforme

Cofactor

Cofactor Comment Organism Structure
additional information carboxylate bridged dimetal cofactor (diiron?) Nostoc punctiforme

General Information

General Information Comment Organism
physiological function saturated fatty acids are converted to alkanes (and unsaturated fatty acids to alkenes) in cyanobacteria entailing scission of the C1-C2 bond of a fatty aldehyde intermediate by the enzyme aldehyde decarbonylase. The in vitro activity of the enzyme depends on the presence of a reducing system, i.e. NADPH, ferredoxin, and ferredoxin reductase Nostoc punctiforme