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Synfacts 2019; 15(11): 1330
DOI: 10.1055/s-0039-1619003
DOI: 10.1055/s-0039-1619003
Peptide Chemistry
Synthesis of Dehydroamino Acid Containing Peptides
Further Information
Publication History
Publication Date:
18 October 2019 (online)
![](https://www.thieme-connect.de/media/synfacts/201911/i_h093_s1_10-1055_s-0039-1619003.gif)
Significance
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.
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Comment
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.
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![](https://www.thieme-connect.de/media/synfacts/201911/i_h093_s1_10-1055_s-0039-1619003.gif)