Synthesis of a novel Fmoc-protected nucleoaminoacid for the solid phase assembly of 4-piperidyl glycine/L-arginine-containing nucleopeptides and preliminary RNA: interaction studies.
In this work, we report the synthesis of a novel Fmoc-protected nucleoaminoacid, based on 4-piperidinyl glycine, carrying the DNA nucleobase on the secondary amino group, suitable for the solid-phase synthesis of nucleopeptides. After ESI-MS and NMR characterization this building block was used for the assembly of a thymine-functionalized tetrapeptide, composed of 4-piperidinyl glycine and L-arginine moieties alternated in the backbone. The ability to interact with RNA and the efficiency in interfering with the reverse transcription of eukaryotic mRNA of the novel nucleo-tetrapeptide found in this study are in favour of the employment of chiral nucleopeptides based on alternate 4-piperidinyl glycine/L-arginine backbone in biomedicine.
Roviello
Giovanni N
GN
Istituto di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, 80134, Naples, Italy. giroviel@unina.it
Crescenzo
Claudia
C
Capasso
Domenica
D
Di Gaetano
Sonia
S
Franco
Simona
S
Bucci
Enrico M
EM
Pedone
Carlo
C
D001120:Arginine / Q000138:chemical synthesis / Q000737:chemistry; D005998:Glycine / Q000138:chemical synthesis / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D012313:RNA / Q000737:chemistry* / Q000235:genetics
D020135:Peptide Nucleic Acids; D012313:RNA; D001120:Arginine; D005998:Glycine