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Synfacts 2019; 15(11): 1330
DOI: 10.1055/s-0039-1619003
Peptide Chemistry
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Dehydroamino Acid Containing Peptides

Contributor(s):
Hisashi Yamamoto
,
Manthena Chaithanya
Okeley NM, Zhu Y, van der Donk WA. * University of Illinois, Urbana, USA
Facile Chemoselective Synthesis of Dehydroalanine-Containing Peptides.

Org. Lett. 2000;
2: 3603-3606
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Further Information

Publication History

Publication Date:
18 October 2019 (online)

 
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Key words

dehydroalanine - phenylselenocysteine - oxidative elimination - lanthionines

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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