Backbone Modifications of Aromatic Peptide Nucleic Acid (APNA) Monomers and Their Hybridization Properties with DNA and RNA

2001 ◽  
Vol 66 (10) ◽  
pp. 3372-3379 ◽  
Author(s):  
Lee D. Fader ◽  
Michael Boyd ◽  
Youla S. Tsantrizos
Keyword(s):  
Nucleic Acid ◽  
Peptide Nucleic Acid ◽  
Dna And Rna

Synthesis of α-(R)-/γ-(S)-Dimethyl Substituted Peptide Nucleic Acid Submonomer Using Mitsunobu Reaction

2019 ◽  
Vol 16 (5) ◽  
pp. 437-446
Author(s):  
Ahmed S. Abdelbaky ◽  
Ivan A. Prokhorov ◽  
Igor P. Smirnov ◽  
Kristina M. Koroleva ◽  
Vitaliy I. Shvets ◽  
...  
Keyword(s):  
Nucleic Acid ◽  
Peptide Nucleic Acid ◽  
Solid Phase ◽  
Genetic Diseases ◽  
Mitsunobu Reaction ◽  
Phase Synthesis ◽  
Dna And Rna ◽  
Pna Synthesis ◽  
Biomedical Technologies

One of the major challenges facing modern biochemical and biomedical technologies are finding molecular tools for diagnosis and detection of genetic diseases. In this connection, several classes of oligonucleotides have been developed that can recognize and bind to DNA and RNA with high affinity and sequence selectivity and withstand enzymatic degradation by proteases and nucleases; however, few can traverse the cell membrane on their own. One such promising class of nucleic acid mimics developed in the last two decades which showed good results in vitro, are the peptide nucleic acids (PNAs). New chiral α- and γ-peptide Nucleic Acid (PNA) submonomer with methyl substituents in pseudopeptide backbone were synthesized via Mitsunobu reaction. The α-(R)-/γ-(S)-configuration of the chiral centres will ensure the preorganization of the PNA oligomer into a right-handed helix. The results obtained showed that Boc/Fmoc-submonomer compatible with Boc-protocol PNAs solid-phase synthesis on an MBHA resin. We synthesized simple and efficient α-R-, γ-S-disubstituted PNA submonomer based on L-Ala and D-Ala with the construction of the intermediate pseudopeptide moiety by Mitsunobu reaction for subsequent use in the Boc-Protocol of solid phase PNA synthesis.

A Cyclopentane Conformational Restraint for a Peptide Nucleic Acid:  Design, Asymmetric Synthesis, and Improved Binding Affinity to DNA and RNA

2003 ◽  
Vol 5 (15) ◽  
pp. 2695-2698 ◽  
Author(s):  
Michael C. Myers ◽  
Mark A. Witschi ◽  
Nataliya V. Larionova ◽  
John M. Franck ◽  
Russell D. Haynes ◽  
...  
Keyword(s):  
Nucleic Acid ◽  
Asymmetric Synthesis ◽  
Binding Affinity ◽  
Peptide Nucleic Acid ◽  
Dna And Rna

DNA and RNA binding properties of an arginine-based ‘Extended Chiral Box’ Peptide Nucleic Acid

2011 ◽  
Vol 52 (2) ◽  
pp. 300-304 ◽  
Author(s):  
Alessandro Calabretta ◽  
Tullia Tedeschi ◽  
Roberto Corradini ◽  
Rosangela Marchelli ◽  
Stefano Sforza
Keyword(s):  
Nucleic Acid ◽  
Peptide Nucleic Acid ◽  
Rna Binding ◽  
Binding Properties ◽  
Dna And Rna ◽  
Dna And Rna Binding

Module Strategy for Peptide Ribonucleic Acid (PRNA)–DNA and PRNA–Peptide Nucleic Acid (PNA)–DNA Chimeras: Synthesis and Interaction of Chimeras with DNA and RNA

2016 ◽  
Vol 45 (3) ◽  
pp. 350-352 ◽  
Author(s):  
Ryohei Uematsu ◽  
Masahito Inagaki ◽  
Mitsuo Asai ◽  
Hiroka Sugai ◽  
Yoshiki Maeda ◽  
...  
Keyword(s):  
Nucleic Acid ◽  
Ribonucleic Acid ◽  
Peptide Nucleic Acid ◽  
Dna And Rna

scholarly journals Recent Advances in Chemical Modification of Peptide Nucleic Acids

2012 ◽  
Vol 2012 ◽  
pp. 1-8 ◽  
Author(s):  
Eriks Rozners
Keyword(s):  
Nucleic Acid ◽  
Nucleic Acids ◽  
Peptide Nucleic Acid ◽  
Peptide Nucleic Acids ◽  
Chemical Modifications ◽  
Practical Applications ◽  
High Affinity ◽  
Dna And Rna ◽  
Double Stranded Dna ◽  
Ongoing Effort

Peptide nucleic acid (PNA) has become an extremely powerful tool in chemistry and biology. Although PNA recognizes single-stranded nucleic acids with exceptionally high affinity and sequence selectivity, there is considerable ongoing effort to further improve properties of PNA for both fundamental science and practical applications. The present paper discusses selected recent studies that improve on cellular uptake and binding of PNA to double-stranded DNA and RNA. The focus is on chemical modifications of PNA's backbone and heterocyclic nucleobases. The paper selects representative recent studies and does not attempt to provide comprehensive coverage of the broad and vibrant field of PNA modification.

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