Synthesis of alpha-methyl selenocysteine and its utilization as a glutathione peroxidase mimic.

ABSTRACT: Selenocysteine (Sec) is the 21st amino acid in the genetic code where this amino acid is primarily involved in redox reactions in enzymes because of its high reactivity toward oxygen and related reactive oxygen species. Sec has found wide utility in synthetic peptides, especially as a replacement for cysteine. One limitation of using Sec in synthetic peptides is that it can undergo β-syn elimination reactions after oxidation, rendering the peptide inactive due to loss of selenium. This limitation can be overcome by substituting Cα-H with a methyl group. The resulting Sec derivative is α-methylselenocysteine ((αMe)Sec). Here, we present a new strategy for the synthesis of (αMe)Sec by alkylation of an achiral methyl malonate through the use of a selenium-containing alkylating agent synthesiz

SUBMITTER: Wehrle RJ 

PROVIDER: S-EPMC6785838 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature