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Highly Stereoselective Synthesis of Substituted Prolyl Peptides Using a Combination of Biocatalytic Desymmetrization and Multicomponent Reactions

Authors

  • Anass Znabet,

    1. Department of Chemistry and Pharmaceutical Sciences, Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands), Fax: (+31) 20-598-7488
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  • Eelco Ruijter Dr.,

    1. Department of Chemistry and Pharmaceutical Sciences, Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands), Fax: (+31) 20-598-7488
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  • Frans J. J. de Kanter Dr.,

    1. Department of Chemistry and Pharmaceutical Sciences, Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands), Fax: (+31) 20-598-7488
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  • Valentin Köhler Dr.,

    1. School of Chemistry, Manchester Interdisciplinary Biocentre, University of Manchester, Manchester (UK)
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  • Madeleine Helliwell Dr.,

    1. School of Chemistry, Manchester Interdisciplinary Biocentre, University of Manchester, Manchester (UK)
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  • Nicholas J. Turner Prof. Dr.,

    1. School of Chemistry, Manchester Interdisciplinary Biocentre, University of Manchester, Manchester (UK)
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  • Romano V. A. Orru Prof. Dr.

    1. Department of Chemistry and Pharmaceutical Sciences, Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands), Fax: (+31) 20-598-7488
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  • We thank Dr. M. T. Smoluch for HRMS measurements. A.Z. thanks the Netherlands Organisation for Scientific Research for a Mosaic Fellowship.

Abstract

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Time and pep-tide wait for no man: Optically pure 3,4-disubstituted 1-pyrrolines, generated from the corresponding meso-pyrrolidines by biocatalytic desymmetrization (MAO-N=monoamine oxidase N), react with carboxylic acids and isocyanides in a highly diastereoselective Ugi-type multicomponent reaction to give substituted prolyl peptides of high pharmaceutical relevance.

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