Conjugation of Selenols with Aziridine-2-Carboxylic Acid-Containing Peptides

Abstract

The addition of PhSeH to aziridine-2-carboxylic acid containing peptides is described, thus expanding the scope of nucleophiles for the opening of this class of electrophilic peptide substrates. The process offers a new strategy for the generation of useful phenylselenocysteine derivatives and α-seleno-β-amino acid-containing peptides.

Key words

aziridine - peptide - ligation - selenol - solid-phase

References

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6

A similar regioselectivity effect was also observed in the thiolysis of Azy-containing peptides. See ref. 1k.

9

The seleno-peptide conjugates 18 and 21 were directly isolated following cleavage from the resin, and were assessed to be >90% pure by ¹H NMR.

11

Although solid-phase synthesis of Azy(3-Me)-containing peptides is a highly efficient process, attempts at on-bead selenolysis were not efficient due to competitive unproductive processes such as, inter alia, aziridine N-deacylation.

12

For detailed representative procedures on the solution-phase and solid-phase synthesis of aziridine-containing peptides, see ref. 1k.