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Design and Synthesis of Haptens for the Catalytic Antibody-Promoted Dynamic Kinetic Resolution of Oxazolin-5-ones

  1. Anne Briot1,
  2. Murielle Bujard1,
  3. Véronique Gouverneur2,
  4. Charles Mioskowski1

Article first published online: 10 DEC 2001

DOI: 10.1002/1099-0690(20021)2002:1<139::AID-EJOC139>3.0.CO;2-S

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2002, Issue 1, pages 139–144, January 2002

Additional Information

How to Cite

Briot, A., Bujard, M., Gouverneur, V. and Mioskowski, C. (2002), Design and Synthesis of Haptens for the Catalytic Antibody-Promoted Dynamic Kinetic Resolution of Oxazolin-5-ones. Eur. J. Org. Chem., 2002: 139–144. doi: 10.1002/1099-0690(20021)2002:1<139::AID-EJOC139>3.0.CO;2-S

Author Information

  1. 1

    Université Louis Pasteur de Strasbourg, Laboratoire de Synthèse Bioorganique 74, route du Rhin, B. P. 24, 67401 Illkirch Graffenstaden, France, Fax: (internat.) + 33-3/90244306

  2. 2

    University of Oxford, The Dyson Perrins Laboratory, New Chemistry Laboratory, South Parks Road, OX1 3QT Oxford, UK, Fax: (internat.) + 44-1865/275-644

Publication History

  1. Issue published online: 10 DEC 2001
  2. Article first published online: 10 DEC 2001
  3. Manuscript Received: 21 JUN 2001

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Keywords:

  • Catalytic antibodies;
  • Haptens;
  • Heterocycles;
  • Kinetic resolution;
  • Metathesis

Abstract

The synthesis of the first two haptens designed to elicit catalytic hydrolytic antibodies for the dynamic kinetic resolution of racemic 4-substituted 4H-oxazolin-5-ones is reported. A cyclic phosphinate and a 2,5-dihydro-1H-pyrrolium derivative were chosen as “first generation” haptens. The cyclic phosphinate was designed to mimic the higher energy transition state along the reaction coordinate for the hydrolytic process, while the dihydro-1H-pyrrolium group of the second hapten was selected to generate hydrolytic antibodies that might use a “bait and switch” mechanism. These two haptens were prepared successfully by use of a ring-closing metathesis reaction as the key step. This study is the first pilot investigation towards an antibody-promoted dynamic kinetic resolution and should allow the development of a new biocatalytic route to enantiomerically pure natural and unnatural amino acids.

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