title: Allene Functionalized Azobenzene Linker Enables Rapid and Light-Responsive Peptide Macrocyclization.
abstract: In this manuscript, we describe the efficient synthesis of a bis(allenamide) functionalized water-soluble azobenzene reagent (BSBDA) and its application as a new tool for the rapid generation of visible light-responsive macrocyclic peptides and peptide libraries displayed on the surface of bacteriophage. The allenamide functionality promotes cysteine ligation in model peptides and those displayed on phage with rates 2-3 orders of magnitude faster than the established alkyl halide containing azobenzenes.
authors: Department of Chemistry and ‡Alberta Glycomics Centre, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
authors: Mohammad R
authors: MR
authors: Jafari
authors: Department of Chemistry and ‡Alberta Glycomics Centre, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
authors: Jenner
authors: J
authors: Lakusta
authors: Department of Chemistry and ‡Alberta Glycomics Centre, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
authors: Rylan J
authors: RJ
authors: Lundgren
authors: Department of Chemistry and ‡Alberta Glycomics Centre, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
authors: Ratmir
authors: R
authors: Derda
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D008027:Light; D047028:Macrocyclic Compounds / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D047028:Macrocyclic Compounds; D010455:Peptides; C009850:azobenzene