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Chemoenzymatic Synthesis of Enantiomerically Pure (2S,3R,4S)-4-Hydroxyisoleucine, an Insulinotropic Amino Acid Isolated from Fenugreek Seeds

Authors

  • Valérie Rolland-Fulcrand,

    1. Laboratoire d′Aminoacides, Peptides et Protéines, UMR − CNRS 5810 − Université Montpellier I et II, Place E Bataillon, 34095 Montpellier Cedex 5, France
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  • Marc Rolland,

    1. Laboratoire d′Aminoacides, Peptides et Protéines, UMR − CNRS 5810 − Université Montpellier I et II, Place E Bataillon, 34095 Montpellier Cedex 5, France
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  • Marie-Louise Roumestant,

    1. Laboratoire d′Aminoacides, Peptides et Protéines, UMR − CNRS 5810 − Université Montpellier I et II, Place E Bataillon, 34095 Montpellier Cedex 5, France
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  • Jean Martinez

    1. Laboratoire d′Aminoacides, Peptides et Protéines, UMR − CNRS 5810 − Université Montpellier I et II, Place E Bataillon, 34095 Montpellier Cedex 5, France
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Abstract

A short six-step synthesis of (2S,3R,4S)-4-hydroxyisoleucine (1a) with total control of stereochemistry is reported, the last step being the enzymatic resolution by hydrolysis of a N-phenylacetyl lactone derivative using the commercially available penicillin acylase G immobilized on Eupergit C (E-PAC). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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