1.14.11.21: clavaminate synthase
This is an abbreviated version!
For detailed information about clavaminate synthase, go to the full flat file.
Word Map on EC 1.14.11.21
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1.14.11.21
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clavulanic
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clavuligerus
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alpha-ketoglutarate
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proclavaminic
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beta-lactamase
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dioxygenase
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non-heme
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cs2
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oxygenases
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clavams
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dioxygen
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alpha-ketoglutarate-dependent
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desaturation
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amidinohydrolase
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2-his-1-carboxylate
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synthesis
- 1.14.11.21
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clavulanic
- clavuligerus
- alpha-ketoglutarate
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proclavaminic
- beta-lactamase
- dioxygenase
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non-heme
- cs2
- oxygenases
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clavams
- dioxygen
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alpha-ketoglutarate-dependent
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desaturation
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amidinohydrolase
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2-his-1-carboxylate
- synthesis
Reaction
Synonyms
CAS, CAS1, CAS2, clavaminate synthase 1, clavaminate synthase 2, clavaminic acid synthase, CS, synthase, clavaminate
ECTree
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Reaction
Reaction on EC 1.14.11.21 - clavaminate synthase
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deoxyamidinoproclavaminate + 2-oxoglutarate + O2 = amidinoproclavaminate + succinate + CO2
reaction mechanism
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deoxyamidinoproclavaminate + 2-oxoglutarate + O2 = amidinoproclavaminate + succinate + CO2
reaction mechanism
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deoxyamidinoproclavaminate + 2-oxoglutarate + O2 = amidinoproclavaminate + succinate + CO2
reaction mechanism
deoxyamidinoproclavaminate + 2-oxoglutarate + O2 = amidinoproclavaminate + succinate + CO2
first reaction: catalyses three separate oxidative reactions in the pathway for the biosynthesis of the beta-lactamase inhibitor clavulanate in Streptomyces clavuligerus. The first step (hydroxylation) is separated from the latter two (oxidative cyclization and desaturation) by the action of EC 3.5.3.22, proclavaminate amidinohydrolase. The three reactions are all catalysed at the same nonheme iron site
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deoxyamidinoproclavaminate + 2-oxoglutarate + O2 = amidinoproclavaminate + succinate + CO2
this reaction is due to a proclavaminate amidinohydrolase PAH, gene cla
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deoxyamidinoproclavaminate + 2-oxoglutarate + O2 = amidinoproclavaminate + succinate + CO2
once the oxoferryl species is formed, the oxidative cyclization most likely involves either a mechanism involving C4'(S)-H bond cleavage of the monocyclic beta-lactam ring, or a biosynthetically unprecedented mechanism comprising oxidation of the hydroxyl group of procavaminate to an O-radical, retro-aldol-like decomposition of the O-radical to an aldehyde and a C-centered radical, which is stabilized by the captodative effect, abstraction of a hydrogen atom from the C4'(S) position of the C-centered radical by the Fe(III)-OH species yielding an azomethine ylide, and 1,3-dipolar cycloaddition to the ylide with aldehyde acting as a dipolarophile
deoxyamidinoproclavaminate + 2-oxoglutarate + O2 = amidinoproclavaminate + succinate + CO2
this reaction is due to a proclavaminate amidinohydrolase PAH, gene cla
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deoxyamidinoproclavaminate + 2-oxoglutarate + O2 = amidinoproclavaminate + succinate + CO2
reaction mechanism
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reaction mechanism
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dihydroclavaminate + 2-oxoglutarate + O2 = clavaminate + succinate + CO2 + H2O
reaction mechanism
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dihydroclavaminate + 2-oxoglutarate + O2 = clavaminate + succinate + CO2 + H2O
reaction mechanism
dihydroclavaminate + 2-oxoglutarate + O2 = clavaminate + succinate + CO2 + H2O
kinetic mechanism
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dihydroclavaminate + 2-oxoglutarate + O2 = clavaminate + succinate + CO2 + H2O
substrate-binding mechanism
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dihydroclavaminate + 2-oxoglutarate + O2 = clavaminate + succinate + CO2 + H2O
substrate-binding mechanism
dihydroclavaminate + 2-oxoglutarate + O2 = clavaminate + succinate + CO2 + H2O
third reaction: catalyses three separate oxidative reactions in the pathway for the biosynthesis of the beta-lactamase inhibitor clavulanate in Streptomyces clavuligerus. The first step (hydroxylation) is separated from the latter two (oxidative cyclization and desaturation) by the action of EC 3.5.3.22, proclavaminate amidinohydrolase. The three reactions are all catalysed at the same nonheme iron site
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dihydroclavaminate + 2-oxoglutarate + O2 = clavaminate + succinate + CO2 + H2O
reaction mechanism
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dihydroclavaminate + 2-oxoglutarate + O2 = clavaminate + succinate + CO2 + H2O
reaction mechanism
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reaction mechanism
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proclavaminate + 2-oxoglutarate + O2 = dihydroclavaminate + succinate + CO2 + H2O
reaction mechanism
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proclavaminate + 2-oxoglutarate + O2 = dihydroclavaminate + succinate + CO2 + H2O
reaction mechanism
proclavaminate + 2-oxoglutarate + O2 = dihydroclavaminate + succinate + CO2 + H2O
kinetic mechanism
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proclavaminate + 2-oxoglutarate + O2 = dihydroclavaminate + succinate + CO2 + H2O
substrate-binding mechanism
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proclavaminate + 2-oxoglutarate + O2 = dihydroclavaminate + succinate + CO2 + H2O
substrate-binding mechanism
proclavaminate + 2-oxoglutarate + O2 = dihydroclavaminate + succinate + CO2 + H2O
second reaction: catalyses three separate oxidative reactions in the pathway for the biosynthesis of the beta-lactamase inhibitor clavulanate in Streptomyces clavuligerus. The first step (hydroxylation) is separated from the latter two (oxidative cyclization and desaturation) by the action of EC 3.5.3.22, proclavaminate amidinohydrolase. The three reactions are all catalysed at the same nonheme iron site
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proclavaminate + 2-oxoglutarate + O2 = dihydroclavaminate + succinate + CO2 + H2O
reaction mechanism
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proclavaminate + 2-oxoglutarate + O2 = dihydroclavaminate + succinate + CO2 + H2O
reaction mechanism
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