ASYMMETRIC SYNTHESIS OF PYROGLUTAMIC ACIDS <i>via</i> Ni(II) COMPLEX METHODOLOGY

Authors

  • Nataliya V. Lyutenko V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, 1 Akademika Kukharya St., Kyiv 02094
  • Alexander E. Sorochinsky V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, 1 Akademika Kukharya St., Kyiv 02094
  • Vadim A. Soloshonok Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, San Sebastián 20018 IKERBASQUE, Basque Foundation for Science, Maria Diaz de Haro 3, Bilbao 48013

DOI:

https://doi.org/10.1007/7484

Keywords:

chiral Schiff bases, heterocycles, substituted pyroglutamic acids, tailor-made amino acids, asymmetric synthesis, Michael addition reactions

Abstract

Michael addition reactions between nucleophilic glycine equivalents and α,β-unsaturated carboxylic acid derivatives represent the most methodologically concise and generalized approach to the family of sterically constrained heterocyclic amino acids. Such amino acids are of critical importance in the de novo peptide design and for elucidation of peptide/protein three-dimensional structure and its biological function/activity. This review summarizes key aspects of Michael addition reactions using Ni(II)-templated Schiff bases of glycine in various asymmetric versions placing chiral auxiliary on either Michael donor or acceptor or both.

Author Biographies

Nataliya V. Lyutenko, V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, 1 Akademika Kukharya St., Kyiv 02094

Department of Chemistry of bioactive nitrogen-containing heterocyclic bases, junior researcher

Alexander E. Sorochinsky, V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, 1 Akademika Kukharya St., Kyiv 02094

Department of Fine organic synthesis

Vadim A. Soloshonok, Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, San Sebastián 20018 IKERBASQUE, Basque Foundation for Science, Maria Diaz de Haro 3, Bilbao 48013

Department of Organic Chemistry I, Faculty of Chemistry

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Published

2023-08-09

Issue

Vol. 59 No. 6/7 (2023): Ukrainian impact on heterocyclic chemistry after the three decades of independence

Section

Review Articles