Synthesis, characterization and hybridization studies of new nucleo-gamma-peptides based on diaminobutyric acid.
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-gamma-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 gamma-aminoacid-containing compounds in natural products of biological activity and by the known stability of gamma-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.
Roviello
Giovanni N
GN
Istituto di Biostrutture e Bioimmagini-CNR, Via Mezzocannone 16, Napoli 80134, Italy.
Moccia
M
M
Sapio
R
R
Valente
M
M
Bucci
E M
EM
Castiglione
M
M
Pedone
C
C
Perretta
G
G
Benedetti
E
E
Musumeci
D
D
D000613:Aminobutyrates / Q000737:chemistry*; D001483:Base Sequence; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D008968:Molecular Conformation; D015394:Molecular Structure; D015341:Nucleic Acid Probes / Q000138:chemical synthesis / Q000737:chemistry; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D013696:Temperature
D000613:Aminobutyrates; D015341:Nucleic Acid Probes; D020135:Peptide Nucleic Acids; C005959:2,4-diaminobutyric acid