ASYMMETRIC SYNTHESIS OF CHI-CONSTRAINED GLUTAMIC ACIDS AND RELATED COMPOUNDS VIA MICHAEL ADDITION REACTIONS(Review)

• Date: 2024
• Author Affiliations: Alicja Wzorek — Institute of Chemistry, Jan Kochanowski University in Kielce, Uniwersytecka 7, 25-406 Kielce, Poland; Alexander Sorochinsky — Department of Fine Organic Synthesis, V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, The National Academy of Sciences of Ukraine, 1 Murmanska str., Kyiv 02094, Ukraine; Karel Klika — Molecular Structure Analysis, German Cancer Research Center (DKFZ), ImNeuenheimer Feld 280, 69120 Heidelberg, Germany; Taizo Ono — National Institute of Advanced Industrial Science and Technology, 463-8560, Nagoya, Japan; Jianlin Han — Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China; Vadim Soloshonok — University of Basque Country
• Keywords: keywords
• Main Authors: Wzorek, Alicja, Sorochinsky, Alexander, Klika, Karel, Ono, Taizo, Han, Jianlin, Soloshonok, Vadim
• Format: Article
• Language: English
• Published: V.I.Vernadsky Institute of General and Inorganic Chemistry 2024
• Online Access: https://ucj.org.ua/index.php/journal/article/view/685
• Journal Title: Ukrainian Chemistry Journal

Michael addition reactions involving nucleophilic glycine equivalents and α,β-unsaturated carboxylic acid derivatives offer a concise and generalized methodological approach to synthesizing a family of χ-constrained five-carbon-atom amino acids. These amino acids play a crucial role in de novo peptide design and the elucidation of peptide/protein three-dimensional structures and their biological functions/activities. This review encapsulates the signi­ficant synthetic and methodological advancements in the field to date. Each method discussed includes an evaluation of synthetic opportunities and limitations, practicality and efficiency of the procedures, and mechanistic rationale behind the observed stereochemical preferences.