Accessing the disallowed conformations of peptides employing amide-to-imidate modification?

Chemical Communications Pub Date: 2011-07-20 DOI: 10.1039/C1CC13515E

Abstract

Selective modification of the C-terminal amide in peptides to dihydrooxazine (a novel stable imidate isostere) by intramolecular nucleophilic cyclo-O-alkylation of the corresponding N-(3-bromopropyl)amides results in constraining of the C-terminal residue in natively disallowed conformations both in crystals and in solution.

Graphical abstract: Accessing the disallowed conformations of peptides employing amide-to-imidate modification
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