title: A fascinating journey into history: exploration of the world of isonitriles en route to complex amides.
abstract: We describe herein our recent explorations in the field of isonitrile chemistry. An array of broadly useful coupling methodologies has been developed for the formation of peptidyl and glycopeptidyl amide bonds. We further describe the application of these methods to the syntheses of complex systems, including the cyclic peptide cyclosporine A, constrained peptide systems, and heterocycles.
authors.affiliation: Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10065, USA.
authors.forename: Rebecca M
authors.initials: RM
authors.lastname: Wilson
authors.forename: Jennifer L
authors.initials: JL
authors.lastname: Stockdill
authors.forename: Xiangyang
authors.initials: X
authors.lastname: Wu
authors.forename: Xuechen
authors.initials: X
authors.lastname: Li
authors.forename: Paul A
authors.initials: PA
authors.lastname: Vadola
authors.forename: Peter K
authors.initials: PK
authors.lastname: Park
authors.forename: Ping
authors.initials: P
authors.lastname: Wang
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Danishefsky
mesh_terms: D000577:Amides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D016572:Cyclosporine / Q000138:chemical synthesis / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D000577:Amides; D002264:Carboxylic Acids; D006020:Glycopeptides; D006571:Heterocyclic Compounds; D009570:Nitriles; D010455:Peptides; D013438:Sulfhydryl Compounds; D016572:Cyclosporine