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Synthesis 2022; 54(02): 255-270
DOI: 10.1055/a-1588-9763
DOI: 10.1055/a-1588-9763
short review
Strategies for the Synthesis of Selenocysteine Derivatives
We thank the Agencia Estatal Investigación of Spain (AEI; Grant RTI2018-099592-B-C21) and the EU (Marie-Sklodowska Curie ITN, DIRNANO, Grant Agreement No. 956544). P.O. thanks Universidad de La Rioja for a Ph.D. fellowship.
Abstract
β-Seleno-α-amino acids, known as selenocysteine (Sec) derivatives, have emerged as important targets because of their role in chemical biology, not only as part of selenoproteins with important redox properties, but also because of their activity as antivirals or metabolites effective in inhibiting carcinogenesis. In addition, there is demand for this type of compounds due to their use in native chemical ligation to construct large peptides. Therefore, this review summarizes the various synthetic methods that have been published to construct Sec derivatives. Most of them involve the generation of the C–Se bond by nucleophilic substitution reactions, but other reactions such as radical or multicomponent strategies are also reported. Of particular importance is the Se-Michael addition of Se-nucleophiles to chiral bicyclic dehydroalanines, in which the stereogenic center is generated under complete stereocontrol.
1 Introduction
2 Previously Reviewed Synthesis of Sec
3 Retrosynthesis of Sec Derivatives
4 Sec Derivatives by Nucleophilic Substitutions
5 Sec Derivatives by Radical Processes
6 Sec Derivatives by 1,4-Conjugate Additions
7 Conclusion
Key words
β-seleno-α-amino acids - selenocysteine - selenocystine - retrosynthesis - nucleophilic substitution - 1,4-conjugate addition - photoredoxPublication History
Received: 16 June 2021
Accepted after revision: 16 August 2021
Accepted Manuscript online:
16 August 2021
Article published online:
06 October 2021
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