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2-Amino-4-bromobutanoic Acid

A Versatile Reagent for the Synthesis of Nonnatural Amino Acids

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Abstract

(2S)- and (2R)-2-Amino-4-bromobutanoic acid were prepared starting from N-Boc-glutamic acid α tert-butyl ester. The double tert-butyl protection was necessary to prevent a partial racemisation during Barton’s radical decarboxylation used to transform the γ-carboxylic group into a bromide. This bromide reacted with different nitrogen, oxygen and sulphur nucleophiles to give nonnatural amino acids characterised by basic or heterocyclic side chains. The title compound was also used to prepare a conformationally constrained peptidomimetic.

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References and Notes

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Authors and Affiliations

  1. Dipartimento di Chimica, Universtà di Sassari, Via Vienna 2, I-07100, Sassari, Italy

    Paola Ciapetti, Massimo Falorni & Maurizio Taddei

  2. Laboratoire de Pharmacologie Moléculaire, CNRS Centre de Neurochimie, 5, rue Blaise Pascal, F-67084, Strasbourg Cedex, France

    André Mann

Authors
  1. Paola Ciapetti
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  2. Massimo Falorni
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  3. André Mann
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  4. Maurizio Taddei
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Ciapetti, P., Falorni, M., Mann, A. et al. 2-Amino-4-bromobutanoic Acid. Molecules Online 2, 86–93 (1998). https://doi.org/10.1007/s007830050060

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  • DOI: https://doi.org/10.1007/s007830050060

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