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Thioester Hydrolysis and C-C Bond Formation by Carboxymethylproline Synthase from the Crotonase Superfamily

Research Authors
Edward T. Batchelar, Refaat B. Hamed, Christian Ducho, Timothy D. W. Claridge, Mariola J. Edelmann, Benedikt Kessler, Christopher J. Schofield
Research Department
Research Journal
Angew. Chem. Int. Ed., DOI: 10.1002/anie.200803906
Research Rank
1
Research Vol
Vol. 47
Research Year
2008
Research Member
Research Abstract

Enzyme in action: Labeling studies and the finding that carboxymethylproline synthase catalyzes production of deuterated (2S,5S)-6,6′-dimethyl-trans-carboxymethylproline (3) from dimethylmalonyl-CoA (1) and labeled l-pyrroline-5-carboxylate (2) limit possible mechanisms of C-C bond formation and thioester hydrolysis. A key feature in the catalysis is that intermediates are stabilized by hydrogen bonds in the “oxy-anion hole” of the enzyme (dark curve in scheme).