Communication

Thioester Hydrolysis and C[BOND]C Bond Formation by Carboxymethylproline Synthase from the Crotonase Superfamily†

  1. Edward T. Batchelar1,‡,
  2. Refaat B. Hamed1,‡,
  3. Christian Ducho Dr.1,3,
  4. Timothy D. W. Claridge Dr.1,
  5. Mariola J. Edelmann2,
  6. Benedikt Kessler Dr.2,
  7. Christopher J. Schofield Prof. Dr.1

Article first published online: 29 OCT 2008

DOI: 10.1002/anie.200803906

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 47, Issue 48, pages 9322–9325, November 17, 2008

Additional Information

How to Cite

Batchelar, Edward T., Hamed, Refaat B., Ducho, C., Claridge, Timothy D. W., Edelmann, Mariola J., Kessler, B. and Schofield, Christopher J. (2008), Thioester Hydrolysis and C[BOND]C Bond Formation by Carboxymethylproline Synthase from the Crotonase Superfamily. Angew. Chem. Int. Ed., 47: 9322–9325. doi: 10.1002/anie.200803906

Author Information

  1. 1

    Department of Chemistry, Oxford University, Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44)-1865-275674 http://www.chem.ox.ac.uk/researchguide/cjschofield.html

  2. 2

    Henry Wellcome Building for Molecular Physiology, Department of Clinical Medicine, University of Oxford (UK)

  3. 3

    Current address: Georg-August-University Göttingen, Department of Chemistry, Institute of Organic and Biomolecular Chemistry, Göttingen (Germany)

  1. ‡

    These authors contributed equally to this work.

  1. †

    We thank the BBSRC (E.T.B.), the Ministry of Higher Education, Egypt (R.B.H.), and the Deutsche Akademie der Naturforscher Leopoldina (Germany) (BMBF-LPD 9901/8-137, C.D.) for funding.

Publication History

  1. Issue published online: 12 NOV 2008
  2. Article first published online: 29 OCT 2008
  3. Manuscript Received: 7 AUG 2008

Funded by

  • BBSRC
  • Ministry of Higher Education, Egypt
  • Deutsche Akademie der Naturforscher Leopoldina (Germany). Grant Number: BMBF-LPD 9901/8-137

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Keywords:

  • biosynthesis;
  • enols;
  • enzyme catalysis;
  • hydrolysis;
  • NMR spectroscopy
Thumbnail image of graphical 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[BOND]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).

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