Literature summary for 1.14.11.21 extracted from

Borowski, T.; de Marothy, S.; Broclawik, E.; Schofield, C.J.; Siegbahn, P.E.
Mechanism for cyclization reaction by clavaminic acid synthase. Insights from modeling studies (2007), Biochemistry, 46, 3682-3691.

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Crystallization (Commentary)

Crystallization (Comment)	Organism
moelcular dynamics simulation, model of the active site	Streptomyces clavuligerus

Organism

Organism	UniProt	Comment	Textmining
Streptomyces clavuligerus	Q05581	-	-

Reaction

Reaction	Comment	Organism	Reaction ID
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	Streptomyces clavuligerus	a

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Release 2023.1 (January 2023)