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Oxopiperazine capping: Formation of oxopiperazine-containing peptoids via C-terminal cyclization

Author:
Lee, Yunjee, Seo, Jiwon
Source:
Tetrahedron letters 2018
ISSN:
0040-4039
Subject:
N-substituted glycines, ammonia, chemical reactions, chemical structure, glutamine, organic compounds, peptides
Abstract:
An unexpected side reaction was observed in peptoids containing a C-terminal carboxamide with a 2-aminoethyl side chain. The reaction proceeded via cyclization and release of NH3, resulting in C-terminal oxopiperazine formation, analogous to pyroglutamate formation from N-terminal glutamine in peptides. Reaction conditions that promote oxopiperazine formation were developed. In particular, the addition of organic bases accelerated the cyclization, thus providing a simple strategy for the post-synthetic C-terminal capping of peptoids.
Agid:
6155816