Microwave Heating Promotes the S-Alkylation of Aziridine Catalyzed by Molecular Sieves: A Post-Synthetic Approach to Lanthionine-Containing Peptides

Aziridine derivatives involved in nucleophilic ring-opening reactions have attracted great interest, since they allow the preparation of biologically active molecules. A chemoselective and mild procedure to convert a peptide cysteine residue into lanthionine via S-alkylation on aziridine substrates...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2021-10, Vol.26 (20), p.6135
Main Authors: Verdoliva, Valentina, Digilio, Giuseppe, Saviano, Michele, De Luca, Stefania
Format: Article
Language:English
Subjects:
Alkylation
Amino acids
aziridine
Biological activity
Catalysis
Investigations
Irradiation
lanthipeptide
microwave irradiation
Molecular sieves
Peptides
Pharmaceutical sciences
post-synthetic modification
Radiation
Ring opening
solid basic catalysis
Solvents
Zeolites
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Summary:Aziridine derivatives involved in nucleophilic ring-opening reactions have attracted great interest, since they allow the preparation of biologically active molecules. A chemoselective and mild procedure to convert a peptide cysteine residue into lanthionine via S-alkylation on aziridine substrates is presented in this paper. The procedure relies on a post-synthetic protocol promoted by molecular sieves to prepare lanthionine-containing peptides and is assisted by microwave irradiation. In addition, it represents a valuable alternative to the stepwise approach, in which the lanthionine precursor is incorporated into peptides as a building block.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules26206135