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Literature summary extracted from

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

Application

EC Number Application Comment Organism
2.3.1.47 agriculture possible target for design of inhibitors as herbicides and antibacterial agents Lysinibacillus sphaericus

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.3.1.47 2-amino-3-hydroxy-2-methylnonadioic acid competitive, transition state analogue Lysinibacillus sphaericus
2.3.1.47 4-carboxybutyl(1-amino-1-carboxyethyl)phosphonate competitive, transition state analogue Lysinibacillus sphaericus
2.3.1.47 8-amino-7-oxo-8-phosphonononanoic acid strong inhibition Lysinibacillus sphaericus
2.3.1.47 D-alanine competitive; Schiff base formation between D- or L-alanine and pyridoxal-5'-phophate in the active site Lysinibacillus sphaericus
2.3.1.47 additional information inhibition mechanism; no inhibition by 8-amino-7-oxo-8-phosphonononanoic acid Lysinibacillus sphaericus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.47 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 ir
2.3.1.47 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 ir
2.3.1.47 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 ir

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.47 Lysinibacillus sphaericus
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.3.1.47 recombinant from E. coli overproducing strain Lysinibacillus sphaericus

Reaction

EC Number Reaction Comment Organism Reaction ID
2.3.1.47 pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein] binding study of L-alanine and D-alanine to the enzyme Lysinibacillus sphaericus
a
2.3.1.47 pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein] Schiff base formation between D- or L-alanine and pyridoxal-5'-phophate in the active site Lysinibacillus sphaericus
a
2.3.1.47 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 Lysinibacillus sphaericus
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Lysinibacillus sphaericus 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ir
2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine second step in biotin biosynthesis Lysinibacillus sphaericus 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ir
2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Lysinibacillus sphaericus 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ir

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.3.1.47 7
-
 assay at Lysinibacillus sphaericus

Cofactor

EC Number Cofactor Comment Organism Structure
2.3.1.47 pyridoxal 5'-phosphate Schiff base formation between D- or L-alanine and pyridoxal-5'-phophate in the active site Lysinibacillus sphaericus

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
2.3.1.47 0.007
-
 8-amino-7-oxo-8-phosphonononanoic acid
-
 Lysinibacillus sphaericus
2.3.1.47 0.068
-
 4-carboxybutyl(1-amino-1-carboxyethyl)phosphonate
-
 Lysinibacillus sphaericus
2.3.1.47 0.08
-
 2-amino-3-hydroxy-2-methylnonadioic acid
-
 Lysinibacillus sphaericus
2.3.1.47 0.59
-
 D-alanine
-
 Lysinibacillus sphaericus