Journal
ORGANIC LETTERS
Volume 25, Issue 36, Pages 6618-6622Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c02289
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1,4-Dione-containing peptides are generated from the cleavage of 2,5-disubstituted furan-containing systems. The generated electrophilic systems react with a-effect nucleophiles, following a Paal-Knorr-like mechanism, to form macrocyclic peptides after resuspension in water. Detailed investigation of the reaction characteristics was performed on supramolecular coiled-coil systems.
1,4-Dione-containing peptides are generated during the cleavage of 2,5-disubstituted furan-containing systems. The generated electrophilic systems then react with a-effect nucleophiles, following a Paal-Knorr-like mechanism, for the generation of macrocyclic peptides, occurring after simple resuspension of the crude peptide in water. Conveniently, the in situ generation of the electrophile from a stable furan ring avoids the complications associated with the synthesis of carbonyl-containing peptides. Detailed investigation of the reaction characteristics was first performed on supramolecular coiled-coil systems.
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