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An efficient approach for solid-phase synthesis of peptidomimetics based on 4-imidazolidinones

✍ Scribed by Markéta Rinnová; Adel Nefzi; Richard A Houghten

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
110 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

An efficient method for the incorporation of an imidazolidinone moiety into peptide sequences via an alkylidene bridge between two neighboring amide bonds is presented. A benzotriazole-mediated reaction of aldehydes with resin-bound peptides provides N-terminal 4-imidazolidinone-peptide derivatives. The generated five-membered ring, which will be expected to have similar properties to 'pseudo-prolines', can be acylated at the secondary amine to allow elongation of the peptide backbone. NMR studies of imidazolidinone-containing peptides show the existence of cis/trans isomerization, typical for proline-based peptides.

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