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Beilstein-Institut, Beilstein Journal of Organic Chemistry, (9), p. 147-154, 2013

DOI: 10.3762/bjoc.9.17

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The diketopiperazine-fused tetrahydro-β-carboline scaffold as a model peptidomimetic with an unusual α-turn secondary structure

Journal article published in 2013 by Francesco Airaghi, Andrea Fiorati ORCID, Giordano Lesma, Manuele Musolino, Alessandro Sacchetti, Alessandra Silvani ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

Aiming at restricting the conformational freedom of tryptophan-containing peptide ligands, we designed a THBC (tetrahydro-β-carboline)-DKP (diketopiperazine)-based peptidomimetic scaffold capable of arranging in an unusual α-turn conformation. The synthesis is based on a diastereoselective Pictet–Spengler condensation to give the THBC core, followed by an intramolecular lactamization to complete the tetracyclic THBC-DKP fused ring system. The presence of conformers bearing the intramolecular thirteen-membered hydrogen bond that characterizes the α-turn structure is confirmed by 1H NMR conformational studies. To the best of our knowledge, this scaffold represents one of the rare examples of a designed constrained α-turn mimic.