BRENDA - Enzyme Database show
show all sequences of 4.1.99.5

Solvent isotope effects on alkane formation by cyanobacterial aldehyde deformylating oxygenase and their mechanistic implications

Waugh, M.W.; Marsh, E.N.; Biochemistry 53, 5537-5543 (2014)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
gene PMT_1231, recombinant expression in Escherichia coli
Prochlorococcus marinus
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
additional information
-
additional information
the rate of alkane formation is the same in D2O or H2O, implying that proton transfer is not a kinetically significant step. When the ratio of protium to deuterium in the product alkane is measured as a function of the mole fraction of D2O, a D2OSIEobs of 2.19 is observed. The SIE is invariant with the mole fraction of D2O, indicating the involvement of a single protic site in the reaction. An iron-bound water molecule is the proton donor to the alkane in the reaction
Prochlorococcus marinus
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
Fe2+
essential, di-iron center
Prochlorococcus marinus
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
a long-chain aldehyde + O2 + 2 NADPH + 2 H+
Prochlorococcus marinus
-
an alkane + formate + H2O + 2 NADP+
-
-
?
a long-chain aldehyde + O2 + 2 NADPH + 2 H+
Prochlorococcus marinus MIT9313
-
an alkane + formate + H2O + 2 NADP+
-
-
?
Organic Solvent Stability
Organic Solvent
Commentary
Organism
additional information
solvent isotope effects on alkane formation by the enzyme have mechanistic implications
Prochlorococcus marinus
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Prochlorococcus marinus
Q7V6D4
-
-
Prochlorococcus marinus MIT9313
Q7V6D4
-
-
Purification (Commentary)
Commentary
Organism
recombinant enzyme from Escherichia coli
Prochlorococcus marinus
Reaction
Reaction
Commentary
Organism
a long-chain aldehyde + O2 + 2 NADPH + 2 H+ = an alkane + formate + H2O + 2 NADP+
proposed mechanism for deformylation of aldehydes by cADO, overview. The rate of alkane formation is the same in D2O or H2O, implying that proton transfer is not a kinetically significant step. When the ratio of protium to deuterium in the product alkane is measured as a function of the mole fraction of D2O, a D2OSIEobs of 2.19 is observed. The SIE is invariant with the mole fraction of D2O, indicating the involvement of a single protic site in the reaction. An iron-bound water molecule is the proton donor to the alkane in the reaction
Prochlorococcus marinus
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
a long-chain aldehyde + O2 + 2 NADPH + 2 H+
-
747074
Prochlorococcus marinus
an alkane + formate + H2O + 2 NADP+
-
-
-
?
a long-chain aldehyde + O2 + 2 NADPH + 2 H+
-
747074
Prochlorococcus marinus MIT9313
an alkane + formate + H2O + 2 NADP+
-
-
-
?
additional information
enzyme assay in anaerobic conditions, quantification of hydrocarbon products by GC-MS
747074
Prochlorococcus marinus
?
-
-
-
-
additional information
enzyme assay in anaerobic conditions, quantification of hydrocarbon products by GC-MS
747074
Prochlorococcus marinus MIT9313
?
-
-
-
-
n-octadecanal + O2 + 2 NADPH + 2 H+
-
747074
Prochlorococcus marinus
n-heptadecane + formate + H2O + 2 NADP+
-
-
-
?
n-octadecanal + O2 + 2 NADPH + 2 H+
-
747074
Prochlorococcus marinus MIT9313
n-heptadecane + formate + H2O + 2 NADP+
-
-
-
?
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
37
-
assay at
Prochlorococcus marinus
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6.8
-
-
Prochlorococcus marinus
Cofactor
Cofactor
Commentary
Organism
Structure
NADPH
-
Prochlorococcus marinus
Cloned(Commentary) (protein specific)
Commentary
Organism
gene PMT_1231, recombinant expression in Escherichia coli
Prochlorococcus marinus
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADPH
-
Prochlorococcus marinus
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
additional information
-
additional information
the rate of alkane formation is the same in D2O or H2O, implying that proton transfer is not a kinetically significant step. When the ratio of protium to deuterium in the product alkane is measured as a function of the mole fraction of D2O, a D2OSIEobs of 2.19 is observed. The SIE is invariant with the mole fraction of D2O, indicating the involvement of a single protic site in the reaction. An iron-bound water molecule is the proton donor to the alkane in the reaction
Prochlorococcus marinus
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
Fe2+
essential, di-iron center
Prochlorococcus marinus
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
a long-chain aldehyde + O2 + 2 NADPH + 2 H+
Prochlorococcus marinus
-
an alkane + formate + H2O + 2 NADP+
-
-
?
a long-chain aldehyde + O2 + 2 NADPH + 2 H+
Prochlorococcus marinus MIT9313
-
an alkane + formate + H2O + 2 NADP+
-
-
?
Organic Solvent Stability (protein specific)
Organic Solvent
Commentary
Organism
additional information
solvent isotope effects on alkane formation by the enzyme have mechanistic implications
Prochlorococcus marinus
Purification (Commentary) (protein specific)
Commentary
Organism
recombinant enzyme from Escherichia coli
Prochlorococcus marinus
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
a long-chain aldehyde + O2 + 2 NADPH + 2 H+
-
747074
Prochlorococcus marinus
an alkane + formate + H2O + 2 NADP+
-
-
-
?
a long-chain aldehyde + O2 + 2 NADPH + 2 H+
-
747074
Prochlorococcus marinus MIT9313
an alkane + formate + H2O + 2 NADP+
-
-
-
?
additional information
enzyme assay in anaerobic conditions, quantification of hydrocarbon products by GC-MS
747074
Prochlorococcus marinus
?
-
-
-
-
additional information
enzyme assay in anaerobic conditions, quantification of hydrocarbon products by GC-MS
747074
Prochlorococcus marinus MIT9313
?
-
-
-
-
n-octadecanal + O2 + 2 NADPH + 2 H+
-
747074
Prochlorococcus marinus
n-heptadecane + formate + H2O + 2 NADP+
-
-
-
?
n-octadecanal + O2 + 2 NADPH + 2 H+
-
747074
Prochlorococcus marinus MIT9313
n-heptadecane + formate + H2O + 2 NADP+
-
-
-
?
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
37
-
assay at
Prochlorococcus marinus
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6.8
-
-
Prochlorococcus marinus
General Information
General Information
Commentary
Organism
additional information
solvent isotope effects on alkane formation by cyanobacterial aldehyde deformylating oxygenase and their mechanistic implications, overview
Prochlorococcus marinus
General Information (protein specific)
General Information
Commentary
Organism
additional information
solvent isotope effects on alkane formation by cyanobacterial aldehyde deformylating oxygenase and their mechanistic implications, overview
Prochlorococcus marinus
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
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, Synechococcus elongatus PCC 7942 R2, Synechocystis sp. PCC 6803
BMC Biotechnol.
17
31-39
2017
-
-
-
-
21
-
-
8
-
2
-
3
-
9
-
-
-
-
-
-
-
-
11
1
-
-
-
28
-
-
-
1
-
-
-
-
-
-
1
-
21
-
-
-
-
8
-
2
-
3
-
-
-
-
-
-
-
-
11
1
-
-
-
28
-
-
-
-
-
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
-
-
4
-
5
-
-
-
-
-
-
6
-
13
-
-
-
-
-
-
-
-
30
-
-
-
-
-
-
-
-
4
-
-
-
-
-
4
4
-
5
-
-
-
-
-
-
-
-
6
-
-
-
-
-
-
-
-
30
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
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
-
-
-
-
-
-
-
3
-
5
-
-
-
-
-
-
-
-
6
2
2
-
-
-
2
-
-
2
-
-
-
-
2
2
2
2
-
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
6
2
2
-
-
-
2
-
-
-
-
4
4
-
-
-
747351
Bao
Structure-oriented substrate ...
Synechococcus elongatus PCC 7942, Synechococcus elongatus PCC 7942 R2
Biotechnol. Biofuels
9
185
2016
-
-
1
-
13
-
-
7
-
-
-
2
-
6
-
-
1
-
-
-
-
-
14
-
1
-
-
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
-
-
-
-
-
-
-
-
4
-
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
-
1
-
-
-
-
-
-
-
-
1
1
-
-
-
747081
Warui
Efficient delivery of long-ch ...
Nostoc punctiforme, Nostoc punctiforme ATCC 29133 / PCC 73102
Biochemistry
54
1006-1015
2015
-
-
-
-
-
-
-
-
-
-
-
2
-
9
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
1
-
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1
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2
-
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-
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-
-
2
-
-
-
-
-
-
-
-
-
-
2
2
-
-
-
748027
Rajakovich
Rapid reduction of the diferr ...
Nostoc punctiforme, Nostoc punctiforme ATCC 29133 / PCC 73102
J. Am. Chem. Soc.
137
11695-11709
2015
-
-
-
-
-
-
-
-
-
1
-
2
-
8
-
-
-
1
-
-
-
-
10
-
1
-
-
-
1
-
-
2
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
1
-
2
-
-
-
-
-
-
-
-
10
-
1
-
-
-
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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1
-
2
-
6
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1
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8
1
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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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8
1
-
-
-
-
-
-
-
-
-
2
2
-
-
-
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
-
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1
-
-
-
-
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10
-
1
-
5
-
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1
-
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1
1
-
8
-
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1
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1
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2
-
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1
-
-
-
-
10
-
1
-
5
-
-
-
-
-
-
3
3
-
-
-
749212
Jia
Structural insights into the ...
Synechococcus elongatus PCC 7942, Synechococcus elongatus PCC 7942 R2
Protein Cell
6
55-67
2015
-
-
1
1
3
-
-
-
-
1
-
2
-
6
-
-
1
1
-
-
-
-
6
1
1
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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
-
-
-
1
-
-
-
-
4
4
-
-
-
726552
Das
Mechanistic insights from reac ...
Nostoc punctiforme
ACS Chem. Biol.
9
570-577
2014
-
-
1
-
-
-
1
-
-
1
-
1
-
2
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1
1
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6
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1
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3
1
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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
-
-
-
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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1
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1
1
1
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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
-
-
-
-
1
-
1
-
2
1
3
-
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1
1
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6
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1
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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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1
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2
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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1
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8
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1
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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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8
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1
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1
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727215
Zhang
Conversion of fatty aldehydes ...
Synechococcus elongatus
Biotechnol. Biofuels
6
86
2013
-
-
1
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1
-
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1
1
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3
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1
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5
1
1
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1
1
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3
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1
3
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1
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1
1
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1
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-
5
1
1
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-
1
1
-
-
-
-
-
-
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-
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727312
Khara
Production of propane and othe ...
Prochlorococcus marinus, Prochlorococcus marinus MIT9313
ChemBioChem
14
1204-1208
2013
-
-
1
-
4
-
-
-
-
1
-
2
-
3
-
-
1
1
-
-
-
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8
-
1
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1
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1
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1
1
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4
-
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1
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2
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1
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8
-
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
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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
-
-
-
-
-
-
1
-
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3
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1
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727001
Li
Evidence for only oxygenative ...
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3
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1
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1
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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
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Conversion of fatty aldehydes ...
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726957
Eser
Oxygen-independent alkane form ...
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4
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4
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15
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4
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4
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4
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713511
Schirmer
Microbial biosynthesis of alka ...
Nostoc punctiforme
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1
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4
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4
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7
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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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Cobalt proteins ...
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A cobalt-porphyrin enzyme conv ...
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1
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648391
Cheesbrough
Alkane biosynthesis by decarbo ...
Pisum sativum
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1
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1
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