title: Thioester-isocyanides: versatile reagents for the synthesis of cycle-tail peptides.
abstract: A novel class of reagents, thioester isocyanides, have been prepared and applied in the synthesis of peptide macrocycles. The isocyanide part of the molecule is deployed in a multicomponent macrocyclization step. This step is followed by chemoselective peptide ligation at the thioester part of the macrocycle. Our method can now be used for rapid assembly and evaluation of cycle-tail peptides.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5H 3H5.
authors.forename: Benjamin H
authors.initials: BH
authors.lastname: Rotstein
authors.forename: David J
authors.initials: DJ
authors.lastname: Winternheimer
authors.forename: Lois M
authors.initials: LM
authors.lastname: Yin
authors.forename: Charles M
authors.initials: CM
authors.lastname: Deber
authors.forename: Andrei K
authors.initials: AK
authors.lastname: Yudin
mesh_terms: D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D004952:Esters / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D020005:Propanols / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated
chemical_list: D003486:Cyanides; D004952:Esters; D010456:Peptides, Cyclic; D020005:Propanols; D012997:Solvents; D013438:Sulfhydryl Compounds; C001337:hexafluoroisopropanol; D006845:Hydrocarbons, Fluorinated