Literature summary for 1.13.12.22 extracted from

Grocholski, T.; Koskiniemi, H.; Lindqvist, Y.; M�nts�l�, P.; Niemi, J.; Schneider, G.
Crystal structure of the cofactor-independent monooxygenase SnoaB from Streptomyces nogalater: implications for the reaction mechanism (2010), Biochemistry, 49, 934-944.

Search for more literature for 1.13.12.22

Cloned(Commentary)

Cloned (Comment)	Organism
expression in Escherichia coli	Streptomyces nogalater

Crystallization (Commentary)

Crystallization (Comment)	Organism
-	Streptomyces nogalater

Protein Variants

Protein Variants	Comment	Organism
H49A	kcat/Km for [4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate is 13% compared to the activity of recombinant wild-type enzyme with N-terminal polyhistidine tag	Streptomyces nogalater
N18A	kcat/Km for [4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate is 1.5% compared to the activity of recombinant wild-type enzyme with N-terminal polyhistidine tag	Streptomyces nogalater
N63A	kcat/Km for [4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate is 1.5% compared to the activity of recombinant wild-type enzyme with N-terminal polyhistidine tag	Streptomyces nogalater
R90E	kcat/Km for [4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate is 17% compared to the activity of recombinant wild-type enzyme with N-terminal polyhistidine tag	Streptomyces nogalater
W67F	kcat/Km for [4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate is 0.5% compared to the activity of recombinant wild-type enzyme with N-terminal polyhistidine tag	Streptomyces nogalater

Inhibitors

Inhibitors	Comment	Organism	Structure
CaCl2	0.1 mM, 9% inhibition	Streptomyces nogalater
CoSO4	0.1 mM, 10% inhibition	Streptomyces nogalater
CuSO4	0.1 mM, 99% inhibition	Streptomyces nogalater
EDTA	1 mM, 8% inhibition	Streptomyces nogalater
FeSO4	0.1 mM, 31% inhibition	Streptomyces nogalater
MgSO4	0.1 mM, 7% inhibition	Streptomyces nogalater

KM Value [mM]

KM Value [mM]	KM Value Maximum [mM]	Substrate	Comment	Organism	Structure
0.068	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme N63A	Streptomyces nogalater
0.094	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, wild-type enzyme, recombinant enzyme with N-terminal polyhistidine tag	Streptomyces nogalater
0.12	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme N18A	Streptomyces nogalater
0.133	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme R90E	Streptomyces nogalater
0.14	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, wild-type enzyme, recombinant enzyme construct with a His tag at the C-terminus	Streptomyces nogalater
0.15	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme H49A	Streptomyces nogalater
0.22	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme W67F	Streptomyces nogalater

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate + O2	Streptomyces nogalater	the enzyme is involved in the biosynthesis of the aromatic polyketide nogalamycin	[4,5-dihydroxy-9,10-dioxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate + H2O	-	?

Organism

Organism	UniProt	Comment	Textmining
Streptomyces nogalater	O54259	-	-

Purification (Commentary)

Purification (Comment)	Organism
-	Streptomyces nogalater

Reaction

Reaction	Comment	Organism	Reaction ID
deoxynogalonate + O2 = nogalonate + H2O	carbanion mechanism where the deprotonated substrate reacts with molecular oxygen via one electron transfer and formation of a caged radical	Streptomyces nogalater	a

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate + O2	-	Streptomyces nogalater	[4,5-dihydroxy-9,10-dioxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate + H2O	-	?
[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate + O2	the enzyme is involved in the biosynthesis of the aromatic polyketide nogalamycin	Streptomyces nogalater	[4,5-dihydroxy-9,10-dioxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate + H2O	-	?

Synonyms

Synonyms	Comment	Organism
SnoaB	-	Streptomyces nogalater

Temperature Optimum [°C]

Temperature Optimum [°C]	Temperature Optimum Maximum [°C]	Comment	Organism
22	-	assay at	Streptomyces nogalater

Turnover Number [1/s]

Turnover Number Minimum [1/s]	Turnover Number Maximum [1/s]	Substrate	Comment	Organism	Structure
0.02	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme N63A	Streptomyces nogalater
0.02	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme W67F	Streptomyces nogalater
0.03	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme N18A	Streptomyces nogalater
0.3	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme H49A	Streptomyces nogalater
0.3	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme R90E	Streptomyces nogalater
1.4	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, wild-type enzyme, recombinant enzyme with N-terminal polyhistidine tag	Streptomyces nogalater
1.5	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, wild-type enzyme, recombinant enzyme construct with a His tag at the C-terminus	Streptomyces nogalater

pH Optimum

pH Optimum Minimum	pH Optimum Maximum	Comment	Organism
7	-	assay at	Streptomyces nogalater

Cofactor

Cofactor	Comment	Organism	Structure
additional information	no cofactor detected	Streptomyces nogalater

General Information

General Information	Comment	Organism
physiological function	the enzyme is involved in the biosynthesis of the aromatic polyketide nogalamycin	Streptomyces nogalater

kcat/KM [mM/s]

kcat/KM Value [1/mMs^-1]	kcat/KM Value Maximum [1/mMs^-1]	Substrate	Comment	Organism	Structure
0.068	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme W67F	Streptomyces nogalater
0.22	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme N18A	Streptomyces nogalater
0.23	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme N63A	Streptomyces nogalater
2	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme H49A	Streptomyces nogalater
2.5	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, mutant enzyme R90E	Streptomyces nogalater
11	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, wild-type enzyme, recombinant enzyme construct with a His tag at the C-terminus	Streptomyces nogalater
15	-	[4,5-dihydroxy-10-oxo-3-(3-oxobutanoyl)-9,10-dihydroanthracen-2-yl]acetate	pH 7.0, 22°C, wild-type enzyme, recombinant enzyme with N-terminal polyhistidine tag	Streptomyces nogalater

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Release 2023.1 (January 2023)