Azidopeptide Nucleic Acid. An Alternative Strategy for Solid-Phase Peptide Nucleic Acid (PNA) Synthesis

2003 ◽  
Vol 5 (23) ◽  
pp. 4445-4447 ◽  
Author(s):  
François Debaene ◽  
Nicolas Winssinger
Keyword(s):  
Nucleic Acid ◽  
Peptide Nucleic Acid ◽  
Solid Phase ◽  
Alternative Strategy ◽  
Pna Synthesis

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.

Microwave-assisted solid-phase synthesis of antisense acpP peptide nucleic acid-peptide conjugates active against colistin- and tigecycline-resistant E. coli and K. pneumoniae

2019 ◽  
Vol 168 ◽  
pp. 134-145 ◽  
Author(s):  
Anna Mette Hansen ◽  
Gitte Bonke ◽  
Wouter Frederik Johan Hogendorf ◽  
Fredrik Björkling ◽  
John Nielsen ◽  
...  
Keyword(s):  
Nucleic Acid ◽  
Peptide Nucleic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Peptide Conjugates ◽  
Phase Synthesis ◽  
E Coli ◽  
Microwave Assisted

scholarly journals Towards the Preparation of Novel Re/99mTc Tricarbonyl-Containing Peptide Nucleic Acid Bioconjugates

2011 ◽  
Vol 64 (3) ◽  
pp. 265 ◽  
Author(s):  
Gilles Gasser ◽  
Anna M. Sosniak ◽  
Anna Leonidova ◽  
Henrik Braband ◽  
Nils Metzler-Nolte
Keyword(s):  
Nucleic Acid ◽  
Click Chemistry ◽  
Sodium Azide ◽  
Peptide Nucleic Acid ◽  
Solid Phase

A novel azido derivative of the di-(2-picolyl)amide (Dpam) ligand, namely 3-azido-N,N-bis-pyridin-2-ylmethyl-propionamide (3), was prepared from 3-bromo-N,N-bis(pyridin-2-ylmethyl)propanamide (2) with an excess of sodium azide in DMSO. 3 was then reacted, by CuI-catalyzed [3 + 2] cycloaddition (often referred to as ‘Click Chemistry’), with the previously reported alkyne-containing peptide nucleic acid (PNA) monomer Fmoc-1-OtBu to give the Dpam-containing PNA monomer (Fmoc-4-OtBu) in 44% yield. It was also demonstrated that 3 could be reacted by Click Chemistry, on the solid phase, to an alkyne-containing PNA oligomer (Alkyne-PNA) to yield Dpam-PNA. Our attempts to complex Dpam-PNA with [NEt4]2[ReBr3(CO)3] and [99mTc(CO)3(H2O)3]+ are also discussed in detail.

An Efficient, Convenient Solid-Phase Synthesis of Amino Acid-Modified Peptide Nucleic Acid Monomers and Oligomers

2006 ◽  
Vol 17 (2) ◽  
pp. 551-558 ◽  
Author(s):  
Baghavathy S. Balaji ◽  
Fabio Gallazzi ◽  
Fang Jia ◽  
Michael R. Lewis
Keyword(s):  
Amino Acid ◽  
Nucleic Acid ◽  
Peptide Nucleic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

Peptide Nucleic Acid Monomers: A Convenient and Efficient Synthetic Approach to Fmoc/Boc Monomers

2012 ◽  
Vol 65 (5) ◽  
pp. 539 ◽  
Author(s):  
Elisse C. Browne ◽  
Steven J. Langford ◽  
Belinda M. Abbott
Keyword(s):  
Nucleic Acid ◽  
Peptide Nucleic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Cost Effective ◽  
Synthetic Approach ◽  
Phase Synthesis ◽  
Cost Effective Method

A convenient and cost-effective method for the synthesis of Fmoc/Boc-protected peptide nucleic acid monomers is described. The Fmoc/Boc strategy was developed in order to eliminate the solubility issues during peptide nucleic acid solid-phase synthesis, in particular that of the cytosine monomer, that occurred when using the commercialized Bhoc chemistry approach.

A Platform for Both Solid-Phase Peptide Nucleic Acid Oligomer Synthesis and Subsequent in Situ Detection and Quantification of Nucleic Acid Sequences

2006 ◽  
Vol 8 (5) ◽  
pp. 639-642 ◽  
Author(s):  
Mark C. McCairn ◽  
Marcus D. Hughes ◽  
Anna V. Hine ◽  
Andrew J. Sutherland
Keyword(s):  
Nucleic Acid ◽  
Peptide Nucleic Acid ◽  
Solid Phase ◽  
In Situ Detection ◽  
Detection And Quantification ◽  
Nucleic Acid Sequences

APPLICATION OF MITSUNOBU REACTION TO SOLID-PHASE PEPTIDE NUCLEIC ACID (PNA) MONOMER SYNTHESIS

2002 ◽  
Vol 21 (11-12) ◽  
pp. 883-889 ◽  
Author(s):  
Bogdan Falkiewicz
Keyword(s):  
Nucleic Acid ◽  
Peptide Nucleic Acid ◽  
Solid Phase ◽  
Mitsunobu Reaction

Solid phase synthesis of peptide nucleic acid-peptide conjugates

2005 ◽  
pp. 299-300
Author(s):  
Lynn Mayfield ◽  
Revathi Katipally ◽  
Carla Simmons ◽  
David R. Corey
Keyword(s):  
Nucleic Acid ◽  
Peptide Nucleic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Peptide Conjugates ◽  
Phase Synthesis
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