Peptide macrocyclisation <i>via</i> intramolecular interception of visible-light-mediated desulfurisation
Frances R. Smith, Declan Meehan, Rhys C. Griffiths, Harriet Knowles, Peiyu Zhang, Huw E. L. Williams, Andrew J. Wilson, Nicholas J. Mitchell
Abstract
the installation of a hydrocarbon linkage. We explore the limits of this chemistry using a range of model peptides of increasing length and complexity, including peptides of biological/therapeutic relevance. The method is applied to replace the native disulfide of the peptide hormone, oxytocin, with a proteolytically/redox-stable hydrocarbon, and internal macrocyclisation of an MCL-1-binding peptide.
Topics & Concepts
Intramolecular forceInterceptionPeptideChemistryStereochemistryBiologyBiochemistryEcologyChemical Synthesis and AnalysisPhotochromic and Fluorescence ChemistryRadical Photochemical Reactions