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

Amino Acids

Volumn 39, Issue 3, 2010, Pages 795-800

  Roviello, Giovanni N ^a   Crescenzo, Claudia ^a   Capasso, Domenica ^b   Di Gaetano, Sonia ^a   Franco, Simona ^a   Bucci, Enrico M ^a   Pedone, Carlo ^b  

^a CNR   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

CD; Nucleopeptide; RNA; RT PCR

Indexed keywords

4 PIPERIDYL GLYCINE; 9 FLUORENYLMETHOXYCARBONYL N (4 PIPERIDYL)GLYCINE; 9 FLUORENYLMETHOXYCARBONYL N [1' (THYMIN 1 YLACETYL) 4' PIPERIDYL]GLYCINE; AMINO ACID DERIVATIVE; ARGININE DERIVATIVE; MESSENGER RNA; NUCLEIC ACID BASE; NUCLEOPEPTIDE DERIVATIVE; OLIGOMER; TETRAPEPTIDE; THYMINE; UNCLASSIFIED DRUG; ARGININE; GLYCINE; PEPTIDE NUCLEIC ACID; RNA;

AMINO ACID SYNTHESIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CIRCULAR DICHROISM; ELECTROSPRAY MASS SPECTROMETRY; HELA CELL; PRIORITY JOURNAL; PROTEIN INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLID PHASE SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; CHEMICAL STRUCTURE; CHEMISTRY; GENETICS; HELA CELL LINE; HUMAN; SYNTHESIS;

ARGININE; GLYCINE; HELA CELLS; HUMANS; MOLECULAR STRUCTURE; PEPTIDE NUCLEIC ACIDS; RNA;

EUKARYOTA;

EID: 77956922342     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-010-0532-4     Document Type: Article

References (12)

1. Bell NM, Micklefield J (2009) Chemical modification of oligonucleotides for therapeutic, bioanalytical and other applications. Chembiochem 10 (17):2691-2703. doi:10.1002/cbic.200900341
2. Diederichsen U (1996) Pairing properties of alanyl peptide nucleic acids containing an amino acid backbone with alternating configuration. Angew Chem Int Ed Engl 35:445-448
3. Dragulescu-Andrasi A, Rapireddy S, He G, Bhattacharya B, Hyldig-Nielsen JJ, Zon G, Ly DH (2006) Cell-permeable peptide nucleic acid designed to bind to the 5'-untranslated region of E-cadherin transcript induces potent and sequence-specific antisense effects. J Am Chem Soc 128:16104-16112
4. Geotti-Bianchini P, Beyrath J, Chaloin O, Formaggio F, Bianco A (2008) Design and synthesis of intrinsically cell-penetrating nucleopeptides. Org Biomol Chem 6:3661-3663
5. Katritzky AR, Narindoshvili T (2008) Chiral peptide nucleic acid monomers (PNAM) with modified backbones. Org Biomol Chem 6:3171-3176
6. Krzyzanowska D, Lisowski M, Kochman M (1998) UV-difference and CD spectroscopy studies on juvenile hormone binding to its carrier protein. J Pept Res 51:96-102
7. Lonkar PS, Kumar VA (2004) Design and synthesis of conforma-tionally frozen peptide nucleic acid backbone: chiral piperidine PNA as a hexitol nucleic acid surrogate. Bioorg Med Chem Lett 14:2147-2149
8. Lonkar PS, Kumar VA (2005) trans-5-Aminopipecolyl-aegPNA chimera: design, synthesis, and study of binding preferences with DNA/RNA in duplex/triplex mode. J Org Chem 70:6956-6959
9. Moggio L, Romanelli A, Gambari R, Bianchi N, Borgatti M, Fabbri E, Mancini I, di Blasio B, Pedone C, Messere A (2007) Alternate PNA-DNA chimeras (PNA-DNA)(n): synthesis, binding properties and biological activity. Biopolymers 88:815-822
10. Nielsen PE, Egholm M, Berg RM, Buchardt O (1991) Sequence selective recognition of DNA by strand displacement with thymine-substituted polyamide. Science 254:1497-1500
11. Rocchi R, Borin G, Marchiori F, Moroder L, Peggion E, Scoffone E, Crescenzi V, Quadrifoglio F (1972) Interaction of S-protein with S-peptide and with synthetic S-peptide analogs. A spectroscopic and calorimetric investigation. Biochemistry 11:50-57
12. Roviello GN, Musumeci D, De Cristofaro A, Capasso D, Di Gaetano S, Bucci EM, Pedone C (2010) Alternate dab-aegPNAs: synthesis, nucleic acid binding studies and biological activity. Mol Biosyst 6 (1):189-195. doi:10.1039/b910278g