On-resin macrocyclization of peptides via intramolecular SnAr reactions.
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.
Fotsch
C
C
Department of Transplantation, Novartis Pharmaceuticals, East Hanover, NJ 07936, USA.
Kumaravel
G
G
Sharma
S K
SK
Wu
A D
AD
Gounarides
J S
JS
Nirmala
N R
NR
Petter
R C
RC
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
D010456:Peptides, Cyclic; D012116:Resins, Plant; C100032:tocinoic acid; D010121:Oxytocin