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.
Synthesis, characterization and hybridization studies of new nucleo-γ-peptides based on diaminobutyric acid / Roviello, G. N.; Moccia, M.; Sapio, R.; Valente, M.; Bucci, E. M.; Castiglione, M.; Pedone, Carlo; Perretta, G.; Benedetti, Ettore; Musumeci, Domenica. - In: JOURNAL OF PEPTIDE SCIENCE. - ISSN 1075-2617. - 12:12(2006), pp. 829-835. [10.1002/psc.819]
Synthesis, characterization and hybridization studies of new nucleo-γ-peptides based on diaminobutyric acid
PEDONE, CARLO;BENEDETTI, ETTORE;MUSUMECI, DOMENICA
2006
Abstract
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.File | Dimensione | Formato | |
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