BRENDA - Enzyme Database show
show all sequences of 2.3.1.47

Slow-binding and competitive inhibition of 8-amino-7-oxopelargonate synthase, a pyridoxal-5'-phosphate-dependent enzyme involved in biotin biosynthesis, by substrate and intermediate analogs: kinetic and binding studies

Ploux, O.; Breyne, O.; Carillon, S.; Marquet, A.; Eur. J. Biochem. 259, 63-70 (1999)

Data extracted from this reference:

Application
Application
Commentary
Organism
agriculture
possible target for design of inhibitors as herbicides and antibacterial agents
Lysinibacillus sphaericus
Inhibitors
Inhibitors
Commentary
Organism
Structure
2-amino-3-hydroxy-2-methylnonadioic acid
competitive, transition state analogue
Lysinibacillus sphaericus
4-carboxybutyl(1-amino-1-carboxyethyl)phosphonate
competitive, transition state analogue
Lysinibacillus sphaericus
8-amino-7-oxo-8-phosphonononanoic acid
strong inhibition
Lysinibacillus sphaericus
D-alanine
competitive; Schiff base formation between D- or L-alanine and pyridoxal-5'-phophate in the active site
Lysinibacillus sphaericus
additional information
inhibition mechanism; no inhibition by 8-amino-7-oxo-8-phosphonononanoic acid
Lysinibacillus sphaericus
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
6-carboxyhexanoyl-CoA + L-alanine
Lysinibacillus sphaericus
i.e. pimeloyl-CoA
8-amino-7-oxononanoate + CoA + CO2
i.e. 7-oxo-8-amino-pelargonic acid
Lysinibacillus sphaericus
ir
6-carboxyhexanoyl-CoA + L-alanine
Lysinibacillus sphaericus
second step in biotin biosynthesis
8-amino-7-oxononanoate + CoA + CO2
i.e. 7-oxo-8-amino-pelargonic acid
Lysinibacillus sphaericus
ir
6-carboxyhexanoyl-CoA + L-alanine
Lysinibacillus sphaericus
reaction in biotin biosynthesis
8-amino-7-oxononanoate + CoA + CO2
i.e. 7-oxo-8-amino-pelargonic acid
Lysinibacillus sphaericus
ir
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Lysinibacillus sphaericus
-
-
-
Purification (Commentary)
Commentary
Organism
recombinant from E. coli overproducing strain
Lysinibacillus sphaericus
Reaction
Reaction
Commentary
Organism
pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
binding of pimeloyl-CoA causes a conformational change in the active site; binding study of L-alanine and D-alanine to the enzyme; Schiff base formation between D- or L-alanine and pyridoxal-5'-phophate in the active site
Lysinibacillus sphaericus
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
6-carboxyhexanoyl-CoA + L-alanine
i.e. pimeloyl-CoA
487054
Lysinibacillus sphaericus
8-amino-7-oxononanoate + CoA + CO2
i.e. 7-oxo-8-amino-pelargonic acid
487054
Lysinibacillus sphaericus
ir
6-carboxyhexanoyl-CoA + L-alanine
second step in biotin biosynthesis
487054
Lysinibacillus sphaericus
8-amino-7-oxononanoate + CoA + CO2
i.e. 7-oxo-8-amino-pelargonic acid
487054
Lysinibacillus sphaericus
ir
6-carboxyhexanoyl-CoA + L-alanine
reaction in biotin biosynthesis
487054
Lysinibacillus sphaericus
8-amino-7-oxononanoate + CoA + CO2
i.e. 7-oxo-8-amino-pelargonic acid
487054
Lysinibacillus sphaericus
ir
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7
-
assay at
Lysinibacillus sphaericus
Cofactor
Cofactor
Commentary
Organism
Structure
pyridoxal 5'-phosphate
Schiff base formation between D- or L-alanine and pyridoxal-5'-phophate in the active site
Lysinibacillus sphaericus
Ki Value [mM]
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.007
-
8-amino-7-oxo-8-phosphonononanoic acid
-
Lysinibacillus sphaericus
0.068
-
4-carboxybutyl(1-amino-1-carboxyethyl)phosphonate
-
Lysinibacillus sphaericus
0.08
-
2-amino-3-hydroxy-2-methylnonadioic acid
-
Lysinibacillus sphaericus
0.59
-
D-alanine
-
Lysinibacillus sphaericus
Application (protein specific)
Application
Commentary
Organism
agriculture
possible target for design of inhibitors as herbicides and antibacterial agents
Lysinibacillus sphaericus
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
pyridoxal 5'-phosphate
Schiff base formation between D- or L-alanine and pyridoxal-5'-phophate in the active site
Lysinibacillus sphaericus
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
2-amino-3-hydroxy-2-methylnonadioic acid
competitive, transition state analogue
Lysinibacillus sphaericus
4-carboxybutyl(1-amino-1-carboxyethyl)phosphonate
competitive, transition state analogue
Lysinibacillus sphaericus
8-amino-7-oxo-8-phosphonononanoic acid
strong inhibition
Lysinibacillus sphaericus
D-alanine
competitive; Schiff base formation between D- or L-alanine and pyridoxal-5'-phophate in the active site
Lysinibacillus sphaericus
additional information
inhibition mechanism; no inhibition by 8-amino-7-oxo-8-phosphonononanoic acid
Lysinibacillus sphaericus
Ki Value [mM] (protein specific)
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.007
-
8-amino-7-oxo-8-phosphonononanoic acid
-
Lysinibacillus sphaericus
0.068
-
4-carboxybutyl(1-amino-1-carboxyethyl)phosphonate
-
Lysinibacillus sphaericus
0.08
-
2-amino-3-hydroxy-2-methylnonadioic acid
-
Lysinibacillus sphaericus
0.59
-
D-alanine
-
Lysinibacillus sphaericus
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
6-carboxyhexanoyl-CoA + L-alanine
Lysinibacillus sphaericus
i.e. pimeloyl-CoA
8-amino-7-oxononanoate + CoA + CO2
i.e. 7-oxo-8-amino-pelargonic acid
Lysinibacillus sphaericus
ir
6-carboxyhexanoyl-CoA + L-alanine
Lysinibacillus sphaericus
second step in biotin biosynthesis
8-amino-7-oxononanoate + CoA + CO2
i.e. 7-oxo-8-amino-pelargonic acid
Lysinibacillus sphaericus
ir
6-carboxyhexanoyl-CoA + L-alanine
Lysinibacillus sphaericus
reaction in biotin biosynthesis
8-amino-7-oxononanoate + CoA + CO2
i.e. 7-oxo-8-amino-pelargonic acid
Lysinibacillus sphaericus
ir
Purification (Commentary) (protein specific)
Commentary
Organism
recombinant from E. coli overproducing strain
Lysinibacillus sphaericus
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
6-carboxyhexanoyl-CoA + L-alanine
i.e. pimeloyl-CoA
487054
Lysinibacillus sphaericus
8-amino-7-oxononanoate + CoA + CO2
i.e. 7-oxo-8-amino-pelargonic acid
487054
Lysinibacillus sphaericus
ir
6-carboxyhexanoyl-CoA + L-alanine
second step in biotin biosynthesis
487054
Lysinibacillus sphaericus
8-amino-7-oxononanoate + CoA + CO2
i.e. 7-oxo-8-amino-pelargonic acid
487054
Lysinibacillus sphaericus
ir
6-carboxyhexanoyl-CoA + L-alanine
reaction in biotin biosynthesis
487054
Lysinibacillus sphaericus
8-amino-7-oxononanoate + CoA + CO2
i.e. 7-oxo-8-amino-pelargonic acid
487054
Lysinibacillus sphaericus
ir
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7
-
assay at
Lysinibacillus sphaericus
Other publictions for EC 2.3.1.47
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)
736245
Fan
Structure and function of Myco ...
Mycolicibacterium smegmatis, Mycolicibacterium smegmatis ATCC 700084
Int. J. Biochem. Cell Biol.
58
71-80
2015
-
1
1
1
-
-
-
-
-
-
-
2
-
6
-
-
-
-
-
-
-
-
2
1
-
-
-
-
-
-
-
1
-
-
-
-
1
1
1
1
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
2
1
-
-
-
-
-
-
-
-
-
2
2
-
-
-
736946
Hahn
Triazolyl phenyl disulfides: 8 ...
Arabidopsis thaliana
Pestic. Biochem. Physiol.
125
78-83
2015
-
1
1
-
-
-
8
-
-
-
-
1
-
3
-
-
1
-
-
1
-
-
1
-
1
-
-
-
1
-
-
-
-
-
5
-
1
1
-
-
-
-
5
8
-
-
-
-
-
1
-
-
-
1
-
1
-
-
1
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
735394
Fan
Purification and X-ray crystal ...
Mycolicibacterium smegmatis, Mycolicibacterium smegmatis ATCC 700084
Acta Crystallogr. Sect. F
70
1372-1375
2014
-
-
1
1
-
-
-
-
-
-
1
2
-
4
-
-
1
-
-
-
-
-
2
1
-
-
-
-
-
-
-
1
-
-
-
-
-
1
1
1
-
-
-
-
-
-
-
-
1
2
-
-
-
1
-
-
-
-
2
1
-
-
-
-
-
-
-
-
-
1
1
-
-
-
719127
Kubota
Detection and characterization ...
Aquifex aeolicus, Escherichia coli, Geobacillus kaustophilus, Geobacillus kaustophilus JCM 12893, Hungateiclostridium thermocellum, Hungateiclostridium thermocellum ATCC 27405, Symbiobacterium thermophilum, Symbiobacterium thermophilum IAM14863, Thermosynechococcus elongatus
Biosci. Biotechnol. Biochem.
76
685-690
2012
-
-
6
-
-
-
-
8
-
-
6
-
-
24
-
-
6
-
-
-
6
-
15
6
6
-
6
-
-
-
-
6
-
-
-
-
-
6
6
-
-
-
-
-
-
8
-
-
6
-
-
-
-
6
-
-
6
-
15
6
6
-
6
-
-
-
-
-
-
-
-
-
7
7
719203
Cho
-
The identification of binding ...
Arabidopsis thaliana
Bull. Korean Chem. Soc.
33
1597-1602
2012
-
-
-
-
-
-
17
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
17
-
-
-
1
-
-
-
17
17
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
718696
Turbeville
Functional asymmetry for the a ...
Escherichia coli
Arch. Biochem. Biophys.
511
107-117
2011
-
-
1
-
1
-
-
4
-
-
-
-
-
1
-
-
1
-
-
-
-
-
1
1
-
-
-
2
-
-
-
1
-
-
-
-
-
1
1
-
1
-
-
-
-
4
-
-
-
-
-
-
-
1
-
-
-
-
1
1
-
-
-
2
-
-
-
-
-
-
-
-
4
4
720623
Hwang
-
Validation of 7-keto-8-aminope ...
Arabidopsis thaliana
Pestic. Biochem. Physiol.
97
24-31
2010
-
-
1
-
-
-
1
-
-
-
1
-
-
1
-
-
1
-
-
2
-
-
1
1
-
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
-
-
1
1
-
-
-
-
1
-
-
-
-
1
-
2
-
-
1
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
702483
Mann
Inhibition of 7,8-diaminopelar ...
Escherichia coli, Escherichia coli C268, Mycobacterium tuberculosis
Biochimie
91
826-834
2009
-
2
2
-
-
-
3
2
-
-
-
3
-
4
-
-
-
-
-
-
-
-
6
2
-
-
-
-
-
-
-
2
11
-
-
-
2
2
2
-
-
-
-
3
11
2
-
-
-
3
-
-
-
-
-
-
-
-
6
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
673041
Kerbarh
Mechanism of alpha-oxoamine sy ...
Escherichia coli
Chem. Commun. (Camb. )
2006
60-62
2006
-
-
-
-
-
-
-
-
-
-
-
1
-
1
-
-
-
1
-
-
-
-
3
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
674626
Bhor
Broad substrate stereospecific ...
Mycobacterium tuberculosis
J. Biol. Chem.
281
25076-25088
2006
-
-
1
-
-
-
2
4
-
-
3
1
-
3
-
-
1
1
-
-
-
-
6
1
1
-
-
3
1
-
-
1
1
-
-
-
-
1
1
-
-
-
-
2
1
4
-
-
3
1
-
-
-
1
-
-
-
-
6
1
1
-
-
3
1
-
-
-
-
-
-
-
-
-
676274
Alexeev
Suicide inhibition of alpha-ox ...
Escherichia coli
Org. Biomol. Chem.
4
1209-1212
2006
-
-
-
1
-
-
1
-
-
-
1
1
-
1
-
-
-
1
-
-
-
-
1
2
-
-
-
-
-
-
-
1
-
-
-
-
-
-
1
1
-
-
-
1
-
-
-
-
1
1
-
-
-
-
-
-
-
-
1
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
676580
Pinon
Biotin synthesis in plants. Th ...
Arabidopsis thaliana
Plant Physiol.
139
1666-1676
2005
-
-
1
-
1
-
-
3
1
-
2
2
-
5
-
-
1
1
-
-
1
-
3
1
1
-
-
2
1
-
-
1
-
-
-
-
-
1
1
-
1
-
-
-
-
3
1
-
2
2
-
-
-
1
-
-
1
-
3
1
1
-
-
2
1
-
-
-
-
-
-
-
-
-
487058
Webster
Mechanism of 8-amino-7-oxonona ...
Escherichia coli
Biochemistry
39
516-528
2000
-
-
1
1
-
-
1
2
-
-
1
2
-
2
-
-
1
1
-
-
-
-
2
-
1
-
-
1
1
-
-
1
-
-
-
-
-
1
1
1
-
-
-
1
-
2
-
-
1
2
-
-
-
1
-
-
-
-
2
-
1
-
-
1
1
-
-
-
-
-
-
-
-
-
487054
Ploux
Slow-binding and competitive i ...
Lysinibacillus sphaericus
Eur. J. Biochem.
259
63-70
1999
-
1
-
-
-
-
5
-
-
-
-
3
-
1
-
-
1
1
-
-
-
-
3
-
-
-
-
-
1
-
-
1
4
-
-
-
1
-
1
-
-
-
-
5
4
-
-
-
-
3
-
-
-
1
-
-
-
-
3
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
487056
Webster
Characterization of 8-amino-7- ...
Escherichia coli, Lysinibacillus sphaericus
Biochem. Soc. Trans.
26
S268
1998
-
-
1
1
-
-
-
2
-
-
1
4
-
2
-
-
1
2
-
-
-
-
4
1
-
-
-
1
-
-
-
2
-
-
-
-
-
1
2
1
-
-
-
-
-
2
-
-
1
4
-
-
-
1
-
-
-
-
4
1
-
-
-
1
-
-
-
-
-
-
-
-
-
-
487057
Alexeev
The crystal structure of 8-ami ...
Escherichia coli
J. Mol. Biol.
284
401-419
1998
-
-
1
1
-
-
-
-
-
-
1
2
-
2
-
-
1
1
-
-
-
-
2
1
-
-
-
-
-
-
-
1
-
-
-
-
-
1
1
1
-
-
-
-
-
-
-
-
1
2
-
-
-
1
-
-
-
-
2
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
487053
Ploux
Mechanistic studies on the 8-a ...
Lysinibacillus sphaericus
Eur. J. Biochem.
236
301-308
1996
-
-
1
-
-
-
-
2
-
-
-
3
-
3
-
-
1
1
-
-
-
-
3
-
-
-
-
1
1
-
-
1
-
-
-
-
-
1
1
-
-
-
-
-
-
2
-
-
-
3
-
-
-
1
-
-
-
-
3
-
-
-
-
1
1
-
-
-
-
-
-
-
-
-
487055
Spinelli
Crystallization and preliminar ...
Lysinibacillus sphaericus
Acta Crystallogr. Sect. D
52
866-868
1996
-
-
-
1
-
-
-
-
-
-
-
-
-
3
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
487048
Ploux
The 8-amino-7-oxopelargonate s ...
Lysinibacillus sphaericus
Biochem. J.
283
327-331
1992
-
-
1
-
-
3
-
2
-
-
3
2
-
6
-
-
1
-
-
-
1
1
2
1
1
-
-
1
2
-
-
1
-
-
-
-
-
1
1
-
-
3
-
-
-
2
-
-
3
2
-
-
-
1
-
-
1
1
2
1
1
-
-
1
2
-
-
-
-
-
-
-
-
-
487049
Otsuka
The Escherichia coli biotin bi ...
Escherichia coli
J. Biol. Chem.
263
19577-19585
1988
-
-
-
-
-
-
-
-
-
-
2
2
-
2
-
-
-
-
-
-
-
-
2
-
-
-
-
-
1
1
-
1
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
2
2
-
-
-
-
-
-
-
-
2
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
1333
Izumi
-
Characterization of biotin bio ...
Lipomyces starkeyi, Lysinibacillus sphaericus, Lysinibacillus sphaericus IFO 3525, Sporidiobolus salmonicolor, Sporobolomyces coprophilus
Agric. Biol. Chem.
45
1983-1989
1981
-
-
-
-
-
-
-
-
-
1
-
9
-
9
-
-
-
-
-
-
4
-
9
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
9
-
-
-
-
-
-
4
-
9
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
487051
Izumi
-
Distribution of 7-keto-8-amino ...
Alcaligenes faecalis, Bacillus subtilis, Citrobacter freundii, Enterobacter cloacae, Erwinia aroidea, Escherichia coli, Klebsiella aerogenes, Kocuria rosea, Lysinibacillus sphaericus, Pseudomonas fluorescens
Agric. Biol. Chem.
37
1335-1340
1973
2
-
-
-
-
-
25
-
-
-
-
20
-
10
-
-
1
-
-
-
11
-
23
-
-
-
-
-
-
-
-
10
6
-
-
2
-
-
10
-
-
-
-
25
6
-
-
-
-
20
-
-
-
1
-
-
11
-
23
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
487052
Izumi
-
Partial purification and some ...
Lysinibacillus sphaericus
Agric. Biol. Chem.
37
1327-1333
1973
-
-
-
-
-
-
21
-
-
1
-
2
-
1
-
-
1
-
-
-
1
1
3
-
2
1
3
-
1
1
-
1
-
-
-
-
-
-
1
-
-
-
-
21
-
-
-
1
-
2
-
-
-
1
-
-
1
1
3
-
2
1
3
-
1
1
-
-
-
-
-
-
-
-
487047
Eidenberg
Synthesis of 7-oxo-8-aminopela ...
Escherichia coli
J. Bacteriol.
96
1291-1297
1968
-
-
-
-
1
-
2
-
-
-
-
2
-
1
-
-
-
-
-
-
1
-
3
-
1
-
-
-
1
-
-
1
-
-
-
-
-
-
1
-
1
-
-
2
-
-
-
-
-
2
-
-
-
-
-
-
1
-
3
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-