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On-resin macrocyclization of peptides via intramolecular SnAr reactions
C Fotsch1, G Kumaravel, S K Sharma
1Department of Transplantation, Novartis Pharmaceuticals, East Hanover, NJ 07936, USA.
Bioorganic & Medicinal Chemistry Letters
|August 28, 1999
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.