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Issue 45, 2012
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Ugi 4-CR/Pictet–Spengler reaction as a short route to tryptophan-derived peptidomimetics

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Abstract

We report here a two step efficient route for the synthesis of 1,2,3,4-tetrahydro-β-carboline (THBC)-based tetracyclic peptidomimetics from a Ugi 4-CR/Pictet–Spengler reaction sequence. Suitably N-protected 2-aminoacetaldehyde was for the first time applied as the carbonyl component in a Ugi four-component reaction, opening the way to the employment of N-protected α-amino acid-derived aldehydes in the same role. The potential of the obtained scaffolds is related to the possibility of further derivatization with the desired pharmacophoric groups, on both the terminal acid and amine functional groups, for the development of conformationally constrained tryptophan-containing peptide ligands. Extensive molecular modeling and 1H NMR studies highlighted a robust, folded, β-turn-like conformation for one of these peptidomimetic compounds.

Graphical abstract: Ugi 4-CR/Pictet–Spengler reaction as a short route to tryptophan-derived peptidomimetics

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Supplementary files

Article information


Submitted
07 Jul 2012
Accepted
01 Oct 2012
First published
02 Oct 2012

Org. Biomol. Chem., 2012,10, 9004-9012
Article type
Paper

Ugi 4-CR/Pictet–Spengler reaction as a short route to tryptophan-derived peptidomimetics

G. Lesma, R. Cecchi, S. Crippa, P. Giovanelli, F. Meneghetti, M. Musolino, A. Sacchetti and A. Silvani, Org. Biomol. Chem., 2012, 10, 9004
DOI: 10.1039/C2OB26301G

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