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Site‐Directed Asymmetric Quaternization of a Peptide Backbone at a C‐Terminal Azlactone

2008; Wiley; Volume: 48; Issue: 4 Linguagem: Inglês

10.1002/anie.200803661

1521-3773

Daisuke Uraguchi, Yoshihiro Asai, Takashi Ooi,

Synthesis and Catalytic Reactions

Dual-purpose activation: Peptide C-terminal azlactones I undergo stereoselective alkylation with high efficiency by the use of a newly devised chiral tetraaminophosphonium salt as a phase-transfer catalyst, and the alkylated azlactone products II can be employed directly for peptide ligation (see scheme, LG=leaving group). In this way, a wide range of chiral quaternary α-amino acid residues can be incorporated at specific sites of a peptide strand.