BRENDA - Enzyme Database
show all sequences of 4.1.99.5

Substrate-triggered addition of dioxygen to the diferrous cofactor of aldehyde-deformylating oxygenase to form a diferric-peroxide intermediate

Pandelia, M.E.; Li, N.; Noergaard, H.; Warui, D.M.; Rajakovich, L.J.; Chang, W.C.; Booker, S.J.; Krebs, C.; Bollinger, J.M.; J. Am. Chem. Soc. 135, 15801-15812 (2013)

Data extracted from this reference:

Activating Compound
Activating Compound
Commentary
Organism
Structure
additional information
the Nostoc punctiforme enzyme is triggered by short-chain (C6-C10) n-aldehyde substrates4 for addition of O2 to its Fe2 II/II cofactor
Nostoc punctiforme
Cloned(Commentary)
Cloned (Commentary)
Organism
gene Npun_R1711, expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
Nostoc punctiforme
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
additional information
-
additional information
complex kinetics of formation of the reaction intermediate, overview
Nostoc punctiforme
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
Fe2+
di-iron enzyme, Moessbauer spectrum of the cofactor during the reaction steps, coordinations of the different cofactor states, e.g. the peroxo-Fe2 III/III intermediate, Fe2 III/III peroxyhemiacetal complex, or a micro-oxo-Fe2 III/III cluster, detailed overview
Nostoc punctiforme
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
additional information
Nostoc punctiforme
cyanobacterial aldehyde-deformylating oxygenases catalyze conversion of saturated or monounsaturated Cn fatty aldehydes to formate and the corresponding Cn-1 alkanes or alkenes, respectively
?
-
-
-
Organism
Organism
UniProt
Commentary
Textmining
Nostoc punctiforme
B2J1M1
gene Npun_R1711
-
Purification (Commentary)
Purification (Commentary)
Organism
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) in an anaerobic chamber, further by metal affinity chromatography
Nostoc punctiforme
Reaction
Reaction
Commentary
Organism
Reaction ID
a long-chain aldehyde + O2 + 2 NADPH + 2 H+ = an alkane + formate + H2O + 2 NADP+
the catalytic mechanism involves attack on the carbonyl of the bound substrate by the reduced O2 moiety to form a Fe2 III/III peroxyhemiacetal complex, which undergoes reductive O-O-bond cleavage, leading to C1-C2 radical fragmentation and formation of the alk(a/e)ne and formate products, detailed overview
Nostoc punctiforme
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
additional information
cyanobacterial aldehyde-deformylating oxygenases catalyze conversion of saturated or monounsaturated Cn fatty aldehydes to formate and the corresponding Cn-1 alkanes or alkenes, respectively
727690
Nostoc punctiforme
?
-
-
-
-
octanal + O2 + 2 NADH + 2 H+
with reducing system NADH/phenazine methosulfate, reaction under anaerobic conditions to protect the cofactor, but the enzyme shows no differences between aerobic and anaerobic condition, meaning that the substrate does not bind tightly to the Fe2 III/III form of the enzyme or that the aldehyde binds in a manner that does not detectably alter its Moessbauer properties
727690
Nostoc punctiforme
heptane + formate + H2O + 2 NAD+
GC-MS poduct analysis
-
-
?
Synonyms
Synonyms
Commentary
Organism
ADO
-
Nostoc punctiforme
aldehyde-deformylating oxygenase
-
Nostoc punctiforme
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
-
assay at
Nostoc punctiforme
Activating Compound (protein specific)
Activating Compound
Commentary
Organism
Structure
additional information
the Nostoc punctiforme enzyme is triggered by short-chain (C6-C10) n-aldehyde substrates4 for addition of O2 to its Fe2 II/II cofactor
Nostoc punctiforme
Cloned(Commentary) (protein specific)
Commentary
Organism
gene Npun_R1711, expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
Nostoc punctiforme
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
additional information
-
additional information
complex kinetics of formation of the reaction intermediate, overview
Nostoc punctiforme
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
Fe2+
di-iron enzyme, Moessbauer spectrum of the cofactor during the reaction steps, coordinations of the different cofactor states, e.g. the peroxo-Fe2 III/III intermediate, Fe2 III/III peroxyhemiacetal complex, or a micro-oxo-Fe2 III/III cluster, detailed overview
Nostoc punctiforme
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
additional information
Nostoc punctiforme
cyanobacterial aldehyde-deformylating oxygenases catalyze conversion of saturated or monounsaturated Cn fatty aldehydes to formate and the corresponding Cn-1 alkanes or alkenes, respectively
?
-
-
-
Purification (Commentary) (protein specific)
Commentary
Organism
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) in an anaerobic chamber, further by metal affinity chromatography
Nostoc punctiforme
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
additional information
cyanobacterial aldehyde-deformylating oxygenases catalyze conversion of saturated or monounsaturated Cn fatty aldehydes to formate and the corresponding Cn-1 alkanes or alkenes, respectively
727690
Nostoc punctiforme
?
-
-
-
-
octanal + O2 + 2 NADH + 2 H+
with reducing system NADH/phenazine methosulfate, reaction under anaerobic conditions to protect the cofactor, but the enzyme shows no differences between aerobic and anaerobic condition, meaning that the substrate does not bind tightly to the Fe2 III/III form of the enzyme or that the aldehyde binds in a manner that does not detectably alter its Moessbauer properties
727690
Nostoc punctiforme
heptane + formate + H2O + 2 NAD+
GC-MS poduct analysis
-
-
?
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
-
assay at
Nostoc punctiforme
General Information
General Information
Commentary
Organism
evolution
cyanobacterial aldehyde-deformylating oxygenases belong to the ferritin-like diiron-carboxylate superfamily of dioxygen-activating proteins
Nostoc punctiforme
General Information (protein specific)
General Information
Commentary
Organism
evolution
cyanobacterial aldehyde-deformylating oxygenases belong to the ferritin-like diiron-carboxylate superfamily of dioxygen-activating proteins
Nostoc punctiforme
Other publictions for EC 4.1.99.5
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Synonyms
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
747409
Wang
Identification of residues im ...
Synechococcus elongatus PCC 7942 = FACHB-805, Synechococcus elongatus PCC 7942 = FACHB-805 R2, Synechocystis sp. PCC 6803
BMC Biotechnol.
17
31-39
2017
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21
-
-
8
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2
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3
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9
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11
1
7
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28
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1
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1
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21
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8
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2
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3
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-
11
1
-
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28
-
-
-
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-
2
2
-
9
9
748564
Patrikainen
Comparison of orthologous cya ...
Nostoc punctiforme, Nostoc punctiforme ATCC 29133 / PCC 73102, Prochlorococcus marinus, Prochlorococcus marinus MIT 9313, Synechococcus sp. RS9917, Synechocystis sp. PCC 6803
Metab. Eng. Commun.
5
9-18
2017
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-
4
-
5
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-
-
-
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6
-
13
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30
-
14
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4
-
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4
4
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5
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6
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30
-
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-
-
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-
746976
Park
Crystal structures of aldehyd ...
Limnothrix redekei, Limnothrix redekei KNUA012, Oscillatoria sp. KNUA011
Biochem. Biophys. Res. Commun.
477
395-400
2016
-
2
2
2
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3
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5
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6
2
4
2
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2
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2
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2
2
2
2
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3
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6
2
2
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2
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4
4
-
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747351
Bao
Structure-oriented substrate ...
Synechococcus elongatus PCC 7942 = FACHB-805, Synechococcus elongatus PCC 7942 = FACHB-805 R2
Biotechnol. Biofuels
9
185
2016
-
-
1
-
13
-
-
7
-
-
-
2
-
6
-
-
1
-
-
-
-
-
14
-
6
1
-
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8
1
-
-
1
-
-
-
-
-
1
1
-
13
-
-
-
-
7
-
-
-
2
-
-
-
1
-
-
-
-
14
-
1
-
-
8
1
-
-
-
-
2
2
-
8
8
747353
Zhang
Microbial synthesis of propan ...
Prochlorococcus marinus, Prochlorococcus marinus MIT 9313
Biotechnol. Biofuels
9
80
2016
-
-
1
-
3
-
-
-
-
-
-
2
-
7
-
-
-
-
-
-
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4
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3
1
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1
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1
1
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3
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2
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4
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1
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1
1
-
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-
747081
Warui
Efficient delivery of long-ch ...
Nostoc punctiforme, Nostoc punctiforme ATCC 29133 / PCC 73102
Biochemistry
54
1006-1015
2015
-
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-
-
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2
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9
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2
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2
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1
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2
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2
2
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748027
Rajakovich
Rapid reduction of the diferr ...
Nostoc punctiforme, Nostoc punctiforme ATCC 29133 / PCC 73102
J. Am. Chem. Soc.
137
11695-11709
2015
-
-
-
-
-
-
-
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-
1
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2
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8
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1
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10
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2
1
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1
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2
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2
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1
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2
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10
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1
-
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-
1
-
-
-
-
1
1
-
-
-
748032
Shokri
Conversion of aldehyde to alk ...
Prochlorococcus marinus, Prochlorococcus marinus MIT 9313
J. Am. Chem. Soc.
137
7686-7691
2015
-
1
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-
-
-
-
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1
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2
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6
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1
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8
1
3
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1
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1
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1
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2
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8
1
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-
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2
2
-
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749051
Hayashi
Role of cysteine residues in ...
Nostoc punctiforme, Nostoc punctiforme ATCC 29133 / PCC 73102
PLoS ONE
10
e0122217
2015
-
-
1
-
8
-
-
1
-
1
-
2
-
7
-
-
1
-
-
-
-
-
10
-
2
1
-
5
-
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1
-
-
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1
1
-
8
-
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1
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1
-
2
-
-
-
1
-
-
-
-
10
-
1
-
5
-
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-
-
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3
3
-
-
-
749212
Jia
Structural insights into the ...
Synechococcus elongatus PCC 7942 = FACHB-805, Synechococcus elongatus PCC 7942 = FACHB-805 R2
Protein Cell
6
55-67
2015
-
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1
1
3
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1
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2
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6
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1
1
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6
1
5
1
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1
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1
1
1
3
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1
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2
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1
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6
1
1
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1
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4
4
-
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-
726552
Das
Mechanistic insights from reac ...
Nostoc punctiforme
ACS Chem. Biol.
9
570-577
2014
-
-
1
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1
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1
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1
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2
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1
1
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6
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3
1
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3
1
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2
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1
2
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1
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1
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1
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1
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6
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1
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3
1
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1
1
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746597
Buer
Insights into substrate and m ...
Prochlorococcus marinus, Prochlorococcus marinus MIT 9313
ACS Chem. Biol.
9
2584-2593
2014
-
-
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1
1
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1
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1
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2
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6
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1
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8
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4
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1
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1
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1
1
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1
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2
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8
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1
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2
2
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747074
Waugh
Solvent isotope effects on al ...
Prochlorococcus marinus, Prochlorococcus marinus MIT9313
Biochemistry
53
5537-5543
2014
-
-
1
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1
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1
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2
1
3
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1
1
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6
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2
1
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1
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1
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1
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6
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1
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1
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1
1
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726548
Aukema
Cyanobacterial aldehyde deform ...
Prochlorococcus marinus, Prochlorococcus marinus MIT 9313
ACS Catal.
3
2228-2238
2013
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1
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6
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8
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727215
Zhang
Conversion of fatty aldehydes ...
Synechococcus elongatus, Synechococcus elongatus PCC 7942
Biotechnol. Biofuels
6
86
2013
-
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1
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1
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1
2
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4
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1
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10
1
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3
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10
1
1
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1
1
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727312
Khara
Production of propane and othe ...
Prochlorococcus marinus, Prochlorococcus marinus MIT9313
ChemBioChem
14
1204-1208
2013
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1
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4
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1
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2
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3
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1
1
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8
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1
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1
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4
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1
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8
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1
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1
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1
1
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727690
Pandelia
Substrate-triggered addition o ...
Nostoc punctiforme
J. Am. Chem. Soc.
135
15801-15812
2013
1
-
1
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1
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1
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1
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2
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1
1
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2
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1
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1
1
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727693
Paul
Probing the mechanism of cyano ...
Nostoc punctiforme
J. Am. Chem. Soc.
135
5234-5237
2013
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1
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3
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1
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727001
Li
Evidence for only oxygenative ...
Prochlorococcus marinus
Biochemistry
51
7908-7916
2012
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1
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4
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1
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3
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1
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1
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1
1
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715293
Warui
Detection of formate, rather t ...
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1
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4
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1
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1
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715300
Li
Conversion of fatty aldehydes ...
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1
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1
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726957
Eser
Oxygen-independent alkane form ...
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15
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8
4
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4
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4
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4
4
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4
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15
-
4
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4
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4
4
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713511
Schirmer
Microbial biosynthesis of alka ...
Nostoc punctiforme
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1
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1
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1
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1
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4
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1
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1
1
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2
1
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1
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4
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7
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2
1
1
1
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1
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1
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1
1
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2
1
1
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648396
Kobayashi
Cobalt proteins ...
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1
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1
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A cobalt-porphyrin enzyme conv ...
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1
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2
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1
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4
1
1
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1
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4
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1
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1
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1
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5
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1
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4
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1
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1
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Cheesbrough
Microsomal preparation from an ...
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2
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1
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1
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1
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9
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1
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1
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2
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1
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1
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1
1
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648391
Cheesbrough
Alkane biosynthesis by decarbo ...
Pisum sativum
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1984
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1
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3
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1
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1
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1
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