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N-aminoimidazolidin-2-one peptidomimetics

Study · Organic letters · 2014 · DOI 10.1021/ol500739k · PMID 24697286

Plain-language summary

Paraphrased from the published abstract below — not a verdict on whether anything works.

This report describes the synthesis of N-aminoimidazolidin-2-one (Aid) peptidomimetics by alkylation of the urea nitrogen of a semicarbazone residue using ethylene bromide. The abstract states the Aid scaffold combines electronic and structural constraints to rigidify the peptide backbone as an aza variant of a Freidinger-Veber lactam. The authors report the synthesis and isolation of 25 Aid peptides, including eight GHRP-6 analogues, to demonstrate the method's utility for controlling conformation.

Abstract

The synthesis of N-aminoimidazolidin-2-one (Aid) peptidomimetics has been achieved by alkylation of the urea nitrogen of a semicarbazone residue using ethylene bromide. The Aid scaffold combines electronic and structural constraints to rigidify the peptide backbone in the equivalent of an aza variant of a Freidinger-Veber lactam. The syntheses and isolation of 25 Aid peptides, including eight GHRP-6 analogues, are reported to demonstrate the utility of this method for controlling conformation.

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