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Literature summary extracted from

  • Ma, G.; Zhu, W.; Su, H.; Cheng, N.; Liu, Y.
    Uncoupled epimerization and desaturation by carbapenem synthase mechanistic insights from QM/MM studies (2015), ACS Catal., 5, 5556-5566 .
No PubMed abstract available

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.14.20.3 Fe2+ iron(II) oxygenase Streptomyces cattleya

Organism

EC Number Organism UniProt Comment Textmining
1.14.20.3 Streptomyces cattleya
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Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.20.3 (3S,5S)-carbapenam-3-carboxylate + 2-oxoglutarate + O2 quantum mechanics/molecular mechanics calculations uncover the reaction mechanism of CarC. The dioxygen binding site on metal is analyzed and it is identified that the Fe(IV)-oxo species has two potential orientations with the oxo group trans to either His101 or His251. The former is energetically unstable, which can rapidly isomerize into the latter by rotation of the oxo group. Arg279 plays important roles in regulating the dioxygen binding and assisting the isomerization of Fe(IV)-oxo species. The calculation results clearly support the stepwise C5-epimerization and C2/3-desaturation processes, involving two complete oxidative cycles. The epimerization process converts (3S,5S)-carbapenam to the initial product (3S,5R)-carbapenam, undergoing H5 atom abstraction by Fe(IV)-O species, inversion of the C5-radical, and reconstitution of the inverted C5-H bond by Tyr165. In the desaturation process, (3S,5R)-carbapenam rebinds the CarC active site with a new orientation different from what (3S,5S)-carbapenam does in the epimerization. In addition, the desaturation across C2-C3 occurs without involving any active site residue other than the Fe(IV)-O center. Whereas Tyr165 is not involved in the desaturation reaction, it plays a key role in binding (3S,5R)-carbapenam. (3S,5R)-Carbapenam is a substrate superior to its epimer (3S,5S)-carbapenam for CarC to produce (5R)-carbapenem by efficient desaturation. In addition, the substrate hydroxylations compete with the target epimerization and desaturation reaction Streptomyces cattleya (5R)-carbapen-2-em-3-carboxylate + succinate + CO2 + H2O
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Synonyms

EC Number Synonyms Comment Organism
1.14.20.3 carbapenem synthase
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Streptomyces cattleya
1.14.20.3 CarC
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Streptomyces cattleya

General Information

EC Number General Information Comment Organism
1.14.20.3 metabolism the enzyme catalyzes the last step of the simple carbapenem biosynthesis Streptomyces cattleya