Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202203120
Keywords
Diastereoselectivity; indolyl glycine; N-Nps imino peptide; organocatalysis; oxidation
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Funding
- Japan Society for the Promotion of Science (JSPS) KAKENHI [JP18K14869, JP20K06965, JP22H05569]
- Research Clusters program of Tokushima University [2201004]
- intelligent Tokushima artificial exosome (iTEX) from Tokushima University
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In this study, N-2-nitrophenylsulfenyl imino dipeptides bearing various functional groups were successfully synthesized and then subjected to diastereoselective indolylation. Each diastereomer of the adduct was selectively obtained using the appropriate chiral phosphoric acid catalysts. These transformations are valuable for synthesizing peptide-based drug candidates containing non-canonical amino acids.
N-2-Nitrophenylsulfenyl imino dipeptides bearing various functional groups were successfully prepared by MnO2-mediated oxidation and then subjected to diastereoselective indolylation. Each diastereomer of the adduct was selectively obtained from the same substrates using the appropriate chiral phosphoric acid catalysts. These transformations would be useful for synthesizing non-canonical amino acid-containing peptides as novel drug candidates.
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