Synthesis, characterization and hybridization studies of new nucleo-γ-peptides based on diaminobutyric acid

• Published in: Journal of peptide science Vol. 12; no. 12; pp. 829 - 835
• Main Authors: Roviello, G. N., Moccia, M., Sapio, R., Valente, M., Bucci, E. M., Castiglione, M., Pedone, C., Perretta, G., Benedetti, E., Musumeci, D.
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.12.2006
• Subjects: Aminobutyrates - chemistry; Base Sequence; Chromatography, High Pressure Liquid; Circular Dichroism; DABA; DNA analogue; Molecular Conformation; Molecular Structure; Nucleic Acid Probes - chemical synthesis; Nucleic Acid Probes - chemistry; Peptide Nucleic Acids - chemical synthesis; Peptide Nucleic Acids - chemistry; PNA; Spectrometry, Mass, Electrospray Ionization; Spectrophotometry, Ultraviolet; Temperature; γ-peptides
• ISSN: 1075-2617; 1099-1387
• DOI: 10.1002/psc.819

In the present work, we report the synthesis and the characterization of a new chiral nucleoaminoacid, in which a diaminobutyric moiety is connected to the DNA nucleobase by an amidic bond, and its oligomerization to give the corresponding nucleo‐γ‐peptide. The ability of this synthetic polymer to bind complementary DNA was studied in order to explore its possible use in antigene/antisense or diagnostic applications. Our interest in the presented DNA analogue was also supported by the importance of γ‐aminoacid‐containing compounds in natural products of biological activity and by the known stability of γ‐peptides to enzymatic degradation. Furthermore, our work could contribute to the study of the role of nucleopeptides as prebiotic material in a PNA world that could successively lead to the actual DNA/RNA/protein world, as recently assumed. Copyright © 2006 European Peptide Society and John Wiley & Sons, Ltd.