BRENDA - Enzyme Database
show all sequences of 1.3.7.5

Biliverdin amides reveal roles for propionate side chains in bilin reductase recognition and in holophytochrome assembly and photoconversion

Shang, L.; Rockwell, N.C.; Martin, S.S.; Lagarias, J.C.; Biochemistry 49, 6070-6082 (2010)

Data extracted from this reference:

Cloned(Commentary)
Cloned (Commentary)
Organism
recombinant expression of GST-tagged PcyA in Escherichia coli
Anabaena sp.
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
biliverdin IXalpha + reduced ferredoxin
Anabaena sp.
-
phycocyanobilin + oxidized ferredoxin
with biliverdins containing a single endovinyl group, such as BV IXalpha, PcyA can generate a mixture of 3E and 3Z products
-
?
biliverdin IXalpha + reduced ferredoxin
Anabaena sp. PCC 7120
-
phycocyanobilin + oxidized ferredoxin
with biliverdins containing a single endovinyl group, such as BV IXalpha, PcyA can generate a mixture of 3E and 3Z products
-
?
Organism
Organism
UniProt
Commentary
Textmining
Anabaena sp.
-
-
-
Anabaena sp. PCC 7120
-
-
-
Purification (Commentary)
Purification (Commentary)
Organism
recombinant GST-tagged PcyA from Escherichia coli by glutathione affinity chromatography
Anabaena sp.
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
biliverdin IXa diamide + reduced ferredoxin
activity only at pH 6.0
724287
Anabaena sp.
? + oxidized ferredoxin
-
-
-
?
biliverdin IXa diamide + reduced ferredoxin
activity only at pH 6.0
724287
Anabaena sp. PCC 7120
? + oxidized ferredoxin
-
-
-
?
biliverdin IXalpha + reduced ferredoxin
-
724287
Anabaena sp.
phycocyanobilin + oxidized ferredoxin
with biliverdins containing a single endovinyl group, such as BV IXalpha, PcyA can generate a mixture of 3E and 3Z products
-
-
?
biliverdin IXalpha + reduced ferredoxin
recombinant ferredoxin from Synechococcus sp. PCC7002
724287
Anabaena sp.
phycocyanobilin + oxidized ferredoxin
with biliverdins containing a single endovinyl group, such as BV IXalpha, PcyA can generate a mixture of 3E and 3Z products
-
-
?
biliverdin IXalpha + reduced ferredoxin
-
724287
Anabaena sp. PCC 7120
phycocyanobilin + oxidized ferredoxin
with biliverdins containing a single endovinyl group, such as BV IXalpha, PcyA can generate a mixture of 3E and 3Z products
-
-
?
biliverdin IXalpha + reduced ferredoxin
recombinant ferredoxin from Synechococcus sp. PCC7002
724287
Anabaena sp. PCC 7120
phycocyanobilin + oxidized ferredoxin
with biliverdins containing a single endovinyl group, such as BV IXalpha, PcyA can generate a mixture of 3E and 3Z products
-
-
?
biliverdin IXalpha 12-monoamide + reduced ferredoxin
-
724287
Anabaena sp.
phycocyanobilin 12-monoamide + oxidized ferredoxin
products are corresponding phycocyanobilin monoamides with a mix of the 3E and 3Z forms
-
-
?
biliverdin IXalpha 12-monoamide + reduced ferredoxin
-
724287
Anabaena sp. PCC 7120
phycocyanobilin 12-monoamide + oxidized ferredoxin
products are corresponding phycocyanobilin monoamides with a mix of the 3E and 3Z forms
-
-
?
biliverdin IXalpha 8-monoamide + reduced ferredoxin
-
724287
Anabaena sp.
phycocyanobilin 8-monoamide + oxidized ferredoxin
products are corresponding phycocyanobilin monoamides with a mix of the 3E and 3Z forms
-
-
?
biliverdin XIII + reduced ferredoxin
-
724287
Anabaena sp.
phycocyanobilin + oxidized ferredoxin
biliverdin XIII contains two endovinyl groups, so PcyA can convert either (or both) to an ethylidene
-
-
?
biliverdin XIIIalpha monoamide + reduced ferredoxin
-
724287
Anabaena sp.
? + oxidized ferredoxin
mixture of products
-
-
?
additional information
semisynthesis of mono- and diamides of biliverdin IXalpha, that function as substrates. The enzyme is accommodating to amidation of the propionic acid side chains of biliverdin IXalpha, which does not require free carboxylic acid side chains to yield its phytobilin product, phycocyanobilin. Bilin amides are assembled with BV-type apophytochromes, demonstrating a role for the 8-propionate in the formation of the spectroscopically native Pr dark states of the biliprotein photosensors. Neither ionizable propionate side chain proves to be essential to primary photoisomerization for BV-type phytochrome. No activity with biliverdin XIIIalpha diamide , but biliverdinXIII diacid is converted into the iso-PthetaB product with moderate yield
724287
Anabaena sp.
?
-
-
-
-
additional information
semisynthesis of mono- and diamides of biliverdin IXalpha, that function as substrates. The enzyme is accommodating to amidation of the propionic acid side chains of biliverdin IXalpha, which does not require free carboxylic acid side chains to yield its phytobilin product, phycocyanobilin. Bilin amides are assembled with BV-type apophytochromes, demonstrating a role for the 8-propionate in the formation of the spectroscopically native Pr dark states of the biliprotein photosensors. Neither ionizable propionate side chain proves to be essential to primary photoisomerization for BV-type phytochrome. No activity with biliverdin XIIIalpha diamide , but biliverdinXIII diacid is converted into the iso-PthetaB product with moderate yield
724287
Anabaena sp. PCC 7120
?
-
-
-
-
Synonyms
Synonyms
Commentary
Organism
PcyA
-
Anabaena sp.
phycocyanobilin:ferredoxin oxidoreductase
-
Anabaena sp.
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6
-
assay with substrate biliverdin diamide
Anabaena sp.
8.5
-
assay at
Anabaena sp.
Cofactor
Cofactor
Commentary
Organism
Structure
Ferredoxin
dependent on
Anabaena sp.
Cloned(Commentary) (protein specific)
Commentary
Organism
recombinant expression of GST-tagged PcyA in Escherichia coli
Anabaena sp.
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
Ferredoxin
dependent on
Anabaena sp.
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
biliverdin IXalpha + reduced ferredoxin
Anabaena sp.
-
phycocyanobilin + oxidized ferredoxin
with biliverdins containing a single endovinyl group, such as BV IXalpha, PcyA can generate a mixture of 3E and 3Z products
-
?
biliverdin IXalpha + reduced ferredoxin
Anabaena sp. PCC 7120
-
phycocyanobilin + oxidized ferredoxin
with biliverdins containing a single endovinyl group, such as BV IXalpha, PcyA can generate a mixture of 3E and 3Z products
-
?
Purification (Commentary) (protein specific)
Commentary
Organism
recombinant GST-tagged PcyA from Escherichia coli by glutathione affinity chromatography
Anabaena sp.
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
biliverdin IXa diamide + reduced ferredoxin
activity only at pH 6.0
724287
Anabaena sp.
? + oxidized ferredoxin
-
-
-
?
biliverdin IXa diamide + reduced ferredoxin
activity only at pH 6.0
724287
Anabaena sp. PCC 7120
? + oxidized ferredoxin
-
-
-
?
biliverdin IXalpha + reduced ferredoxin
-
724287
Anabaena sp.
phycocyanobilin + oxidized ferredoxin
with biliverdins containing a single endovinyl group, such as BV IXalpha, PcyA can generate a mixture of 3E and 3Z products
-
-
?
biliverdin IXalpha + reduced ferredoxin
recombinant ferredoxin from Synechococcus sp. PCC7002
724287
Anabaena sp.
phycocyanobilin + oxidized ferredoxin
with biliverdins containing a single endovinyl group, such as BV IXalpha, PcyA can generate a mixture of 3E and 3Z products
-
-
?
biliverdin IXalpha + reduced ferredoxin
-
724287
Anabaena sp. PCC 7120
phycocyanobilin + oxidized ferredoxin
with biliverdins containing a single endovinyl group, such as BV IXalpha, PcyA can generate a mixture of 3E and 3Z products
-
-
?
biliverdin IXalpha + reduced ferredoxin
recombinant ferredoxin from Synechococcus sp. PCC7002
724287
Anabaena sp. PCC 7120
phycocyanobilin + oxidized ferredoxin
with biliverdins containing a single endovinyl group, such as BV IXalpha, PcyA can generate a mixture of 3E and 3Z products
-
-
?
biliverdin IXalpha 12-monoamide + reduced ferredoxin
-
724287
Anabaena sp.
phycocyanobilin 12-monoamide + oxidized ferredoxin
products are corresponding phycocyanobilin monoamides with a mix of the 3E and 3Z forms
-
-
?
biliverdin IXalpha 12-monoamide + reduced ferredoxin
-
724287
Anabaena sp. PCC 7120
phycocyanobilin 12-monoamide + oxidized ferredoxin
products are corresponding phycocyanobilin monoamides with a mix of the 3E and 3Z forms
-
-
?
biliverdin IXalpha 8-monoamide + reduced ferredoxin
-
724287
Anabaena sp.
phycocyanobilin 8-monoamide + oxidized ferredoxin
products are corresponding phycocyanobilin monoamides with a mix of the 3E and 3Z forms
-
-
?
biliverdin XIII + reduced ferredoxin
-
724287
Anabaena sp.
phycocyanobilin + oxidized ferredoxin
biliverdin XIII contains two endovinyl groups, so PcyA can convert either (or both) to an ethylidene
-
-
?
biliverdin XIIIalpha monoamide + reduced ferredoxin
-
724287
Anabaena sp.
? + oxidized ferredoxin
mixture of products
-
-
?
additional information
semisynthesis of mono- and diamides of biliverdin IXalpha, that function as substrates. The enzyme is accommodating to amidation of the propionic acid side chains of biliverdin IXalpha, which does not require free carboxylic acid side chains to yield its phytobilin product, phycocyanobilin. Bilin amides are assembled with BV-type apophytochromes, demonstrating a role for the 8-propionate in the formation of the spectroscopically native Pr dark states of the biliprotein photosensors. Neither ionizable propionate side chain proves to be essential to primary photoisomerization for BV-type phytochrome. No activity with biliverdin XIIIalpha diamide , but biliverdinXIII diacid is converted into the iso-PthetaB product with moderate yield
724287
Anabaena sp.
?
-
-
-
-
additional information
semisynthesis of mono- and diamides of biliverdin IXalpha, that function as substrates. The enzyme is accommodating to amidation of the propionic acid side chains of biliverdin IXalpha, which does not require free carboxylic acid side chains to yield its phytobilin product, phycocyanobilin. Bilin amides are assembled with BV-type apophytochromes, demonstrating a role for the 8-propionate in the formation of the spectroscopically native Pr dark states of the biliprotein photosensors. Neither ionizable propionate side chain proves to be essential to primary photoisomerization for BV-type phytochrome. No activity with biliverdin XIIIalpha diamide , but biliverdinXIII diacid is converted into the iso-PthetaB product with moderate yield
724287
Anabaena sp. PCC 7120
?
-
-
-
-
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6
-
assay with substrate biliverdin diamide
Anabaena sp.
8.5
-
assay at
Anabaena sp.
General Information
General Information
Commentary
Organism
evolution
comparison and discrimination of two bilin reductase families in bilin amide usage for photoconversions of BV-type and phytobilin-type phytochromes, mechanistic differences, overview
Anabaena sp.
additional information
the NADPH-dependent biliverdin reductases, BVR and BvdR, are less accommodating to amidation of the propionic acid side chains of biliverdin IXR than PcyA, which does not require free carboxylic acid side chains to yield its phytobilin product, phycocyanobilin
Anabaena sp.
General Information (protein specific)
General Information
Commentary
Organism
evolution
comparison and discrimination of two bilin reductase families in bilin amide usage for photoconversions of BV-type and phytobilin-type phytochromes, mechanistic differences, overview
Anabaena sp.
additional information
the NADPH-dependent biliverdin reductases, BVR and BvdR, are less accommodating to amidation of the propionic acid side chains of biliverdin IXR than PcyA, which does not require free carboxylic acid side chains to yield its phytobilin product, phycocyanobilin
Anabaena sp.
Other publictions for EC 1.3.7.5
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)
742318
Ceron-Carrasco
-
First computational step towa ...
Synechocystis sp. PCC 6803
Comput. Theoret. Chem.
1077
58-64
2016
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742524
Hagiwara
Atomic-resolution structure o ...
Synechocystis sp. PCC 6803
FEBS Lett.
590
3425-3434
2016
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724131
Kabasakal
His74 conservation in the bili ...
Synechocystis sp.
Arch. Biochem. Biophys.
537
233-242
2013
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3
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3
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724317
Alvey
Attachment of noncognate chrom ...
Synechococcus sp., Synechococcus sp. 7002
Biochemistry
50
4890-4902
2011
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725252
Alvey
Effects of modified phycobilin ...
Synechococcus sp.
J. Bacteriol.
193
1663-1671
2011
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3
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711117
Wada
One residue substitution in Pc ...
Synechocystis sp.
Biochem. Biophys. Res. Commun.
402
373-377
2010
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712411
Hagiwara
Structural insights into vinyl ...
Synechocystis sp.
J. Biol. Chem.
285
1000-1007
2010
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724287
Shang
Biliverdin amides reveal roles ...
Anabaena sp., Anabaena sp. PCC 7120
Biochemistry
49
6070-6082
2010
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724288
Kohler
Structural basis for hydration ...
Synechocystis sp.
Biochemistry
49
6206-6218
2010
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696870
Zhang
Biosynthesis of fluorescent al ...
Synechocystis sp.
Biotechnol. Appl. Biochem.
52
135-140
2009
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698489
Stoll
Structure of the biliverdin ra ...
Nostoc sp. PCC 7120 = FACHB-418, Synechocystis sp.
J. Am. Chem. Soc.
131
1986-1995
2009
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7
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712008
Okada
HO1 and PcyA proteins involved ...
Thermosynechococcus elongatus
FEBS Lett.
583
1251-1256
2009
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685125
Tu
Insight into the radical mecha ...
Nostoc sp. PCC 7120 = FACHB-418
Biochemistry
46
1484-1494
2007
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Kami
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Frankenberg
Functional genomic analysis of ...
Anabaena sp., Nostoc punctiforme, Prochlorococcus sp., Prochlorococcus sp. CCMP1378 / MED4, Synechococcus sp., Synechococcus sp. WH8102, Synechocystis sp.
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Tooley
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