EC Number   |
Reaction |
Reference |
|---|
   1.14.11.21 | 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 |
- |
| 1.14.11.21 | 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 |
685142 |
| 1.14.11.21 | deoxyamidinoproclavaminate + 2-oxoglutarate + O2 = amidinoproclavaminate + succinate + CO2 |
reaction mechanism |
-, 639271, 639274, 639286 |
| 1.14.11.21 | deoxyamidinoproclavaminate + 2-oxoglutarate + O2 = amidinoproclavaminate + succinate + CO2 |
this reaction is due to a proclavaminate amidinohydrolase PAH, gene cla |
-, 639036, 639276, 639277, 639278, 639280 |
| 1.14.11.21 | dihydroclavaminate + 2-oxoglutarate + O2 = clavaminate + succinate + CO2 + H2O |
kinetic mechanism |
639270 |
| 1.14.11.21 | dihydroclavaminate + 2-oxoglutarate + O2 = clavaminate + succinate + CO2 + H2O |
reaction mechanism |
-, 639271, 639272, 639273, 639274, 639275, 639276, 639277, 639278, 639279, 639280, 639281, 639283, 639284, 639286 |
| 1.14.11.21 | dihydroclavaminate + 2-oxoglutarate + O2 = clavaminate + succinate + CO2 + H2O |
substrate-binding mechanism |
639279, 639281 |
| 1.14.11.21 | 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 |
- |
| 1.14.11.21 | proclavaminate + 2-oxoglutarate + O2 = dihydroclavaminate + succinate + CO2 + H2O |
kinetic mechanism |
639270 |
| 1.14.11.21 | proclavaminate + 2-oxoglutarate + O2 = dihydroclavaminate + succinate + CO2 + H2O |
reaction mechanism |
-, 639271, 639272, 639273, 639274, 639275, 639276, 639277, 639278, 639279, 639280, 639281, 639283, 639284, 639286 |
