title: On-resin macrocyclization of peptides via intramolecular SnAr reactions.
abstract: On-resin macrocyclization via an SNAr reaction is employed in the synthesis of tocinoic acid analogs. Specifically, an N-terminal nitrofluorobenzene is attacked by a nucleophilic C-terminal sidechain. The remaining nitro group can be reduced and acylated. NMR is used to compare the conformation of the new macrocyclic peptides to tocinoic acid.
authors.affiliation: Department of Transplantation, Novartis Pharmaceuticals, East Hanover, NJ 07936, USA.
authors.forename: C
authors.initials: C
authors.lastname: Fotsch
authors.forename: G
authors.initials: G
authors.lastname: Kumaravel
authors.forename: S K
authors.initials: SK
authors.lastname: Sharma
authors.forename: A D
authors.initials: AD
authors.lastname: Wu
authors.forename: J S
authors.initials: JS
authors.lastname: Gounarides
authors.forename: N R
authors.initials: NR
authors.lastname: Nirmala
authors.forename: R C
authors.initials: RC
authors.lastname: Petter
mesh_terms: D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010121:Oxytocin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D012116:Resins, Plant / Q000737:chemistry
chemical_list: D010456:Peptides, Cyclic; D012116:Resins, Plant; C100032:tocinoic acid; D010121:Oxytocin