Organic & Biomolecular Chemistry 2010-03-21

Replacement of Ala by Aib improves structuration and biological stability in thymine-based alpha-nucleopeptides.

Piero Geotti-Bianchini, Alessandro Moretto, Cristina Peggion, Julien Beyrath, Alberto Bianco, Fernando Formaggio

Index: Org. Biomol. Chem. 8(6) , 1315-21, (2010)

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Abstract

Three thymine-based nucleo-heptapeptides, each containing two nucleo-amino acids and zero, one or four Aib residues, respectively, have been synthesized. A single Aib residue is enough to promote the adoption of a helical structure in our nucleopeptides and to increase significantly their resistance towards enzymatic degradation. The insertion of four Aib residues, out of seven residues in the sequence, affords a rigid, 3(10)-helical nucleopeptide that is substantially unaffected by serum enzymes and is not cytotoxic.