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Literature summary 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

EC Number Inhibitors Comment Organism Structure
1.14.11.21 4'-ethynyl proclavaminate noncompetitive Streptomyces clavuligerus
1.14.11.21 4'-vinyl proclavaminate noncompetitive Streptomyces clavuligerus
1.14.11.21 4-cyclopropyl proclavaminate noncompetitive Streptomyces clavuligerus

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.14.11.21 0.23
-
 N-alpha-acetyl-L-arginine pH 7.0, 22°C Streptomyces clavuligerus

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.14.11.21 Fe2+ required Streptomyces clavuligerus

Organism

EC Number Organism UniProt Comment Textmining
1.14.11.21 Streptomyces clavuligerus
-
 strain ATCC 27064
-

Reaction

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

Specific Activity [micromol/min/mg]

EC Number Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
1.14.11.21 0.4
-
 65fold purified enzyme Streptomyces clavuligerus

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.11.21 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 ?
1.14.11.21 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 ?
1.14.11.21 dihydroclavaminate + 2-oxoglutarate + O2 stereochemical course of oxygen insertion Streptomyces clavuligerus clavaminate + succinate + CO2 + H2O
-
 ?
1.14.11.21 dihydroclavaminate + 2-oxoglutarate + O2 cyclization Streptomyces clavuligerus clavaminate + succinate + CO2 + H2O
-
 ?
1.14.11.21 additional information specific for 2-oxoglutarate Streptomyces clavuligerus ?
-
 ?
1.14.11.21 additional information 4'-vinyl proclavaminate, 4'-ethynyl proclavaminate, and 4-cyclopropyl proclavaminate are no substrates Streptomyces clavuligerus ?
-
 ?
1.14.11.21 N-alpha-acetyl-L-arginine + 2-oxoglutarate + O2 hydroxylation Streptomyces clavuligerus 4-hydroxy-N-alpha-acetyl-L-arginine + succinate + CO2 + H2O
-
 ?
1.14.11.21 N-alpha-acetyl-L-arginine + 2-oxoglutarate + O2 isozyme CS2 Streptomyces clavuligerus 4-hydroxy-N-alpha-acetyl-L-arginine + succinate + CO2 + H2O
-
 ?
1.14.11.21 proclavaminate + 2-oxoglutarate + O2 (4'RS)-rac-proclavaminate Streptomyces clavuligerus dihydroclavaminate + succinate + CO2 + H2O
-
 ?
1.14.11.21 proclavaminate + 2-oxoglutarate + O2 saturation Streptomyces clavuligerus dihydroclavaminate + succinate + CO2 + H2O
-
 ?
1.14.11.21 proclavaminate + 2-oxoglutarate + O2 stereochemical course of oxygen insertion Streptomyces clavuligerus dihydroclavaminate + succinate + CO2 + H2O
-
 ?

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.14.11.21 22
-
 room temperature, assay at Streptomyces clavuligerus

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.14.11.21 6.4
-
 N-alpha-acetyl-L-arginine pH 7.0, 22°C Streptomyces clavuligerus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.14.11.21 7
-
 assay at Streptomyces clavuligerus

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.14.11.21 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