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.

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.

Reductive Alkylation and Sequential Reductive Alkylation-Click Chemistry for On-Solid-Support Modification of Pyrrolidinyl Peptide Nucleic Acid

2013 ◽  
Vol 24 (4) ◽  
pp. 614-625 ◽  
Author(s):  
Boonsong Ditmangklo ◽  
Chalothorn Boonlua ◽  
Chaturong Suparpprom ◽  
Tirayut Vilaivan
Keyword(s):  
Nucleic Acid ◽  
Click Chemistry ◽  
Peptide Nucleic Acid ◽  
Solid Support ◽  
Reductive Alkylation

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.

scholarly journals ClickIn: a flexible protocol for quantifying mitochondrial uptake of nucleobase derivatives

2017 ◽  
Vol 7 (2) ◽  
pp. 20160117 ◽  
Author(s):  
Kurt Hoogewijs ◽  
Andrew M. James ◽  
Robin A. J. Smith ◽  
Frank Abendroth ◽  
Michael J. Gait ◽  
...  
Keyword(s):  
Nucleic Acid ◽  
Click Chemistry ◽  
Peptide Nucleic Acid ◽  
Mitochondrial Matrix ◽  
Major Difficulty ◽  
Mitochondrial Membranes ◽  
Mitochondrial Import ◽  
Acid Conjugate ◽  
Multiple Molecules

There is an increasing interest in targeting molecules to the mitochondrial matrix. Many proteins are naturally imported through the translocase complexes found in the outer and inner mitochondrial membranes. One possible means for importing molecules is therefore to use a mitochondrial pre-protein as a vector and assess what forms of molecules can be attached to the pre-protein as cargo. A major difficulty with this approach is to ensure that any chimaeric molecule does indeed access the mitochondrial matrix and does not merely associate with the mitochondrial membranes. We have recently demonstrated that click chemistry can be used both to demonstrate convincingly mitochondrial import of a peptide–peptide nucleic acid conjugate and also to quantify the mitochondrial uptake for specific synthetic conjugates. We now report an adaptation of the synthesis to facilitate simple quantification of multiple molecules and hence to calculate the efficiency of their mitochondrial import.

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