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Literature summary for 1.14.11.21 extracted from

  • Iwata-Reuyl, D.; Basak, A.; Silverman, L.S.; Engle, C.A.; Townsend, C.A.
    Synthesis and reaction of potential alternate substrates and mechanism-based inhibitors of clavaminate synthase (1993), J. Nat. Prod., 56, 1373-1396.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
4'-ethynyl proclavaminate noncompetitive Streptomyces clavuligerus
4'-vinyl proclavaminate noncompetitive Streptomyces clavuligerus
4-cyclopropyl proclavaminate noncompetitive Streptomyces clavuligerus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.23
-
N-alpha-acetyl-L-arginine pH 7.0, 22°C Streptomyces clavuligerus

Metals/Ions

Metals/Ions Comment Organism Structure
Fe2+ required Streptomyces clavuligerus

Organism

Organism UniProt Comment Textmining
Streptomyces clavuligerus
-
strain ATCC 27064
-

Reaction

Reaction Comment Organism Reaction ID
dihydroclavaminate + 2-oxoglutarate + O2 = clavaminate + succinate + CO2 + H2O reaction mechanism Streptomyces clavuligerus
proclavaminate + 2-oxoglutarate + O2 = dihydroclavaminate + succinate + CO2 + H2O reaction mechanism Streptomyces clavuligerus

Specific Activity [micromol/min/mg]

Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
0.4
-
65fold purified enzyme Streptomyces clavuligerus

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
deoxyamidinoproclavaminate + 2-oxoglutarate + O2
-
Streptomyces clavuligerus amidinoproclavaminate + succinate + CO2 + H2O 10% of the product is proclavaminate, 90% of the product is E-(2S)-5-amino-2(2'-oxoazetidin-1-yl)-pent-3,4-enoate ?
deoxyamidinoproclavaminate + 2-oxoglutarate + O2 isozyme CS2 Streptomyces clavuligerus E-(2S)-5-amino-2(2'-oxoazetidin-1-yl)-pent-3,4-enoate + succinate + CO2 + H2O + ? 10% of the product is proclavaminate, 90% of the product is E-(2S)-5-amino-2(2'-oxoazetidin-1-yl)-pent-3,4-enoate ?
dihydroclavaminate + 2-oxoglutarate + O2 stereochemical course of oxygen insertion Streptomyces clavuligerus clavaminate + succinate + CO2 + H2O
-
?
dihydroclavaminate + 2-oxoglutarate + O2 cyclization Streptomyces clavuligerus clavaminate + succinate + CO2 + H2O
-
?
additional information specific for 2-oxoglutarate Streptomyces clavuligerus ?
-
?
additional information 4'-vinyl proclavaminate, 4'-ethynyl proclavaminate, and 4-cyclopropyl proclavaminate are no substrates Streptomyces clavuligerus ?
-
?
N-alpha-acetyl-L-arginine + 2-oxoglutarate + O2 hydroxylation Streptomyces clavuligerus 4-hydroxy-N-alpha-acetyl-L-arginine + succinate + CO2 + H2O
-
?
N-alpha-acetyl-L-arginine + 2-oxoglutarate + O2 isozyme CS2 Streptomyces clavuligerus 4-hydroxy-N-alpha-acetyl-L-arginine + succinate + CO2 + H2O
-
?
proclavaminate + 2-oxoglutarate + O2 (4'RS)-rac-proclavaminate Streptomyces clavuligerus dihydroclavaminate + succinate + CO2 + H2O
-
?
proclavaminate + 2-oxoglutarate + O2 saturation Streptomyces clavuligerus dihydroclavaminate + succinate + CO2 + H2O
-
?
proclavaminate + 2-oxoglutarate + O2 stereochemical course of oxygen insertion Streptomyces clavuligerus dihydroclavaminate + succinate + CO2 + H2O
-
?

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
22
-
room temperature, assay at Streptomyces clavuligerus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
6.4
-
N-alpha-acetyl-L-arginine pH 7.0, 22°C Streptomyces clavuligerus

pH Optimum

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

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
additional information
-
additional information Ki of 4'-vinyl proclavaminate, 4'-ethynyl proclavaminate, and 4-cyclopropyl proclavaminate is in the range of 2-10 mM Streptomyces clavuligerus