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Org Lett. 2018 Mar 16;20(6):1621-1625. doi: 10.1021/acs.orglett.8b00364. Epub 2018 Mar 5.

Disulfide-Bridged Peptides That Mediate Enantioselective Cycloadditions through Thiyl Radical Catalysis.

Author information

1
Department of Chemistry , Yale University , 225 Prospect Street , New Haven , Connecticut 06520 , United States.

Abstract

An enantioselective vinylcyclopropane ring-opening/cycloaddition cascade is described. The active thiyl radical catalysts are generated in situ via UV light-promoted homolysis of cystine-based dimers. Amide-functionalization of the peptide at the 4-proline position is essential for effective asymmetric induction. Stereochemical communication is dependent on steric interactions with this substituent that are enforced by H-bonding to the peptide backbone.

PMID:
29504763
PMCID:
PMC5963541
DOI:
10.1021/acs.orglett.8b00364
[Indexed for MEDLINE]
Free PMC Article

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