Visible-Light Mediated Deoxygenation of Carboxylic Acid for Late-Stage Peptide Modification Targeting Dehydroalanine
Guangjun Bao, Peng Wang, Xiaomin Guo, Yiping Li, Zeyuan He, Xinyi Song, E Ruiyao, Tingli Yu, Junqiu Xie, Wangsheng Sun
Abstract
A visible-light mediated deoxygenative radical addition of carboxylic acids to dehydroalanines has been disclosed. The method can be used in β-acyl alanine derivative synthesis, including those chiral and deuterated variants, and late-stage peptide modification with various functional groups, both in the homogeneous phase and on the resin in SPPS. It provides a new tool kit for rapid construction of bioactive peptide analogues, which has been demonstrated by modification of the antimicrobial peptide Feleucin-K3.
Topics & Concepts
ChemistryDehydroalanineDeoxygenationPeptideCombinatorial chemistryCarboxylic acidVisible spectrumLysinePeptide synthesisAntimicrobialHomogeneousStereochemistryAmino acidOrganic chemistryBiochemistryCatalysisOptoelectronicsThermodynamicsPhysicsChemical Synthesis and AnalysisRadical Photochemical ReactionsMicrobial Natural Products and Biosynthesis