Strategies for the Synthesis of Selenocysteine Derivatives

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 - photoredox

Publication 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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