Catalytic, One-Pot Synthesis of β-Amino Acids from α-Amino Acids. Preparation of α,β-Peptide Derivatives

descriptionPublicationkeyboard_double_arrow_right Article 24 Apr 2009 English Publisher:American Chemical Society (ACS)Journal:The Journal of Organic Chemistry, volume 74, pages 4,655-4,665 (issn: 0022-3263, eissn: 1520-6904,

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Authors: Saavedra, Carlos Javier; Hernández, Rosendo; Boto, Alicia; Álvarez, Eleuterio;

doi: 10.1021/jo9004487

handle: 10261/37537

Catalytic, One-Pot Synthesis of β-Amino Acids from α-Amino Acids. Preparation of α,β-Peptide Derivatives

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Abstract

The one-pot conversion of readily available alpha-amino acid into beta-amino acid derivatives was carried out in good yields. The method is a sequential process initiated by a tandem radical decarboxylation-oxidation reaction; the resulting acyliminium ion was trapped by silyl ketenes. Stoichiometric and catalytic versions of this reaction were developed and then applied to prepare modified di- and tripeptides. Interestingly, some tripeptides formed expanded beta-turns in the solid state.

This work was supported by the Investigation Programmes CTQ2006-14260/PPQ and PPQ2003-01379 of the Plan Nacional de Investigación Científica, Desarrollo e Innovación Tecnológica, Ministerio de Educación y Ciencia and Ministerio de Ciencia y Tecnología, Spain. We also acknowledge financial support from FEDER funds. C.J.S. thanks the CSIC for an I3P contract, and the Gobierno de Canarias-BIOSIGMA SL for a research contract.

11 páginas, 2 figuras, 6 tablas, 3 esquemas.

Peer reviewed

Related Organizations

Spanish National Research Council
Spain
Institute for Chemical Research
Spain

Keywords

Stereoisomerism, Molecular structure, Oligopeptides, Catalysis, Oxidation-reduction

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