Synthesis of Dehydroamino Acid Containing Peptides
Facile Chemoselective Synthesis of Dehydroalanine-Containing Peptides.
Org. Lett. 2000;
18 October 2019 (online)
The α,β-unsaturated amino acids dehydroalanine and dehydrobutyrine are present in various natural products and polypeptides. The authors have developed a method for the chemoselective synthesis of dehydroalanine (dha) residues by oxidative elimination of nonnatural amino acids.
Chemoselective, site-specific incorporation of dha residues into peptides was achieved by the oxidative elimination of Se-phenylselenocysteine. Furthermore, cyclic lanthionines were synthesized by intramolecular Michael addition of cysteine onto the Dha residues.