Synthesis of a thymine-functionalized nucleoamino acid for the solid phase assembly of cationic nucleopeptides

Amino Acids

Volumn 45, Issue 4, 2013, Pages 779-784

  Roviello, Giovanni N ^a   Musumeci, Domenica ^b   D'Alessandro, Cristian ^a   Pedone, Carlo ^b  

^a CNR   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

CD; l Lysine; Nucleopeptide

Indexed keywords

AMINO ACID DERIVATIVE; CATIONIC NUCLEOPEPTIDE DERIVATIVE; LYSINE; MONOMER; NUCLEIC ACID BASE; NUCLEOAMINO ACID; OLIGOMER; PEPTIDE NUCLEIC ACID; RESIN; THYMINE; UNCLASSIFIED DRUG; WATER;

AMINO ACID SYNTHESIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CIRCULAR DICHROISM; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; SOLID PHASE SYNTHESIS; SOLUBILITY; TEMPERATURE MEASUREMENT;

AMINO ACIDS; CATIONS; MOLECULAR STRUCTURE; OLIGOPEPTIDES; THYMINE;

EID: 84885216747     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-013-1520-2     Document Type: Article

References (21)

1. Abramova TV, Vlassov VV, Zarytova VF, Ivanova EM, Kuligina EA, Ryte AS (1991) The Effect of Oligodeoxyribonucleotide Terminal Phosphate and Ribose Modification on the Interactions of Oligonucleotides with Cells and Intracellular Stability. Nucleosides Nucleotides 10:639-640
2. Bell NM, Micklefield J (2009) Chemical modification of oligonucleotides for therapeutic, bioanalytical and other applications. ChemBioChem. doi: 10.1002/cbic.200900341
3. Calabretta A, Tedeschi T, Di Cola G, Corradini R, Sforza S, Marchelli R (2009) Arginine-based PNA microarrays for APOE genotyping. Mol BioSyst 5:1323-1330
4. D'Alonzo D, Guaragna A, Palumbo G (2011) Exploring the role of chirality in nucleic acid recognition. Chem Biodivers 8:373-413
5. D'Onofrio J, de Champdoré M, De Napoli L, Montesarchio D, Di Fabio G (2005) Glycomimetics as decorating motifs for oligonucleotides: solid-phase synthesis, stability, and hybridization properties of carbopeptoid- oligonucleotide conjugates. Bioconjug Chem 16:1299-1309
6. 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
7. Katritzky AR, Narindoshvili T (2008) Chiral peptide nucleic acid monomers (PNAM) with modified backbones. Org Biomol Chem 6:3171-3176
8. Petraccone L, Pagano B, Esposito V, Randazzo A, Piccialli G, Barone G, Mattia CA, Giancola C (2005) Thermodynamics and kinetics of PNA-DNA quadruplex-forming chimeras. J Am Chem Soc 127:16215-16223
9. Roviello GN, Moccia M, Sapio R, Valente M, Bucci EM, Castiglione M, Pedone C, Perretta G, Benedetti E, Musumeci D (2006) Synthesis, characterization and hybridization studies of new nucleo-gamma-peptides based on diaminobutyric acid. J Pept Sci 12:829-835
10. Roviello GN, Musumeci D, Moccia M, Castiglione M, Sapio R, Valente M, Bucci EM, Perretta G, Pedone C (2007) dabPNA: design, synthesis, and DNA binding studies. Nucleosides Nucleotides Nucleic Acids 26:1307-1310
11. Roviello GN, Musumeci D, De Cristofaro A, Capasso D, Di Gaetano S, Bucci EM, Pedone C (2009) Alternate dab-aegPNAs: synthesis, nucleic acid binding studies and biological activity. Mol BioSyst 6:189-195
12. Roviello GN, Benedetti E, Pedone C, Bucci EM (2010a) Nucleobase- containing peptides: an overview of their characteristic features and applications. Amino Acids 39:45-57
13. Roviello GN, Musumeci D, Pedone C, Bucci EM (2010b) Synthesis, characterization and hybridization studies of an alternate nucleo epsilon/gamma-peptide: complexes formation with natural nucleic acids. Amino Acids 38:103-111
14. Roviello GN, Musumeci D, Bucci EM, Pedone C (2011) Evidences for supramolecular organization of nucleopeptides: synthesis, spectroscopic and biological studies of a novel dithymine l-serine tetrapeptide. Mol BioSyst 7:1073-1080
15. Roviello GN, Roviello G, Musumeci D, Bucci EM, Pedone C (2012) Dakin-West reaction on 1-thyminyl acetic acid for the synthesis of 1,3-bis(1-thyminyl)-2- propanone, a heteroaromatic compound with nucleopeptide-binding properties. Amino Acids 43:1615-1623
16. Sawa N, Wada T, Inoue Y (2010) Synthesis and DNA-recognition behavior of a novel peptide ribonucleic acid with a serine backbone (oxa-PRNA). Tetrahedron 66:344-349
17. Simeone L, Irace C, Di Pascale A, Ciccarelli D, D'Errico G, Montesarchio D (2012) Synthesis, self-aggregation and bioactivity properties of a cationic aminoacyl surfactant, based on a new class of highly functionalized nucleolipids. Eur J Med Chem 57:429-440
18. van der Laan AC, van Amsterdam I, Tesser GI, Van Boom JH, Yeheskiel EK (1998) Synthesis of chirally pure ornithine-based PNA analogues. Nucleosides Nucleotides 17:219-231
19. Wada T, Minamimoto N, Inaki Y, Inoue Y (2000) Peptide ribonucleic acids (PRNA). 2. A novel strategy for active control of DNA recognition through borate ester formation. J Am Chem Soc 122:6900-6910
20. Zarra R, Montesarchio D, Coppola C, Di Micco S, Bifulco G, Izzo I, De Riccardis F (2009) Design, synthesis, and hybridisation of water-soluble, peptoid nucleic acid oligomers tagged with thymine. Eur J Org Chem 35:6113-6120
21. Zatsepin TS, Romanova EA, Stetsenko DA, Gait MJ, Oretskaya TS (2003) Synthesis of 2′-modified oligonucleotides containing aldehyde or ethylenediamine groups. Nucleosides Nucleotides Nucleic Acids 22:1383-1385