Category: 186046-81-1

Peng, Xiaohua published the artcileA Template-Mediated Click-Click Reaction: PNA-DNA, PNA-PNA (or Peptide) Ligation, and Single Nucleotide Discrimination, Category: pyrimidines, the publication is European Journal of Organic Chemistry (2010), 4194-4197, S4194/1-S4194/19, database is CAplus and MEDLINE.

A highly efficient chem. ligation was developed for quant. conjugation of PNA with DNA (PNA or peptide) by using the copper-catalyzed azide-alkyne cycloaddition reaction. Whereas PNAs with an alkyne at the C-terminus and an azide at the N-terminus have been used, an efficient click-click reaction occurs. The PNA click ligation is sequence specific and capable of single nucleotide discrimination.

European Journal of Organic Chemistry published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, Category: pyrimidines.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Ok, Tae-Dong published the artcileGNA/aegPNA Chimera Loaded with RNA Binding Preference, Related Products of pyrimidines, the publication is Chemistry – An Asian Journal (2011), 6(8), 1996-1999, database is CAplus and MEDLINE.

The authors have found a very simple strategy to improve binding preference of aegPNA [aeg = N-(2-aminoethyl)glycine] to RNA/DNA. Inspired by the structure of the GNA (glycol nucleic acid) monomer, a highly simple chiral PNA monomer was designed. By incorporating a few chiral acyclic γ-amino acid mols. into the achiral aegPNA backbone, the authors were able to make a chimeric PNA (chiPNA) with better RNA selectivity as well as antiparallel selectivity. The authors feel, to the best of their knowledge, this is the simplest monomeric unit that induces aegPNA to discriminate between RNA and DNA. Finally, the authors demonstrate that the chip-based competition-binding assay is an alternative tool to the quant. anal. of binding selectivities of modified PNAs. The authors believe that chiPNAs will expand the utility of PNAs and find diverse applications related to RNA targets in the future.

Chemistry – An Asian Journal published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, Related Products of pyrimidines.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Browne, Elisse C. published the artcileSynthesis and effects of conjugated tocopherol analogues on peptide nucleic acid hybridisation, Safety of 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, the publication is Organic & Biomolecular Chemistry (2013), 11(39), 6744-6750, database is CAplus and MEDLINE.

To the N-terminus of a nonamer peptide nucleic acid sequence, H-GCACGACTT-NH₂, was attached a number of lipophilic conjugate mols. including three synthetic tocopherol (vitamin E) analogs. Studies were then undertaken with complementary PNA and DNA sequences to explore the effects of the conjugates using the techniques of UV monitored melting curves and isothermal calorimetry. Duplex formation was observed when the benzopyran group of vitamin E was conjugated. However, in the presence of the phytyl chain of vitamin E, binding was found to be temperature dependent.

Organic & Biomolecular Chemistry published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, Safety of 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Hirano, Taisuke published the artcilePeptide-nucleic acids (PNAs) with pyrimido[4,5-d]pyrimidine-2,4,5,7-(1H,3H,6H,8H)-tetraone (PPT) as a universal base: their synthesis and binding affinity for oligodeoxyribonucleotides, Safety of 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, the publication is Organic & Biomolecular Chemistry (2009), 7(14), 2905-2911, database is CAplus and MEDLINE.

Peptide-nucleic acids (PNAs) including pyrimido[4,5-d]pyrimidine-2,4,5,7-(1H,3H,6H,8H)-tetraone (PPT) as a nucleobase were synthesized, and their binding affinity for the complementary oligodeoxyribonucleotides was investigated. The authors found that PNAs with one or two PPT(s) and natural nucleobases (i.e., adenine, cytosine, guanine, or thymine) have excellent binding affinity for oligodeoxyribonucleotides with complementary bases at the positions facing the natural nucleobases, and with adenine, cytosine, guanine, and thymine at the positions opposite PPT in PNAs. The binding affinity of the PPT-containing PNA is higher than or comparable to that of a PNA consisting of all complementary natural nucleobases, viz. a PNA with a suitable natural nucleobase in place of PPT in the PPT-containing PNA. Consequently, it was concluded that PPT serves as a useful universal base that can recognize all natural nucleobases.

Organic & Biomolecular Chemistry published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, Safety of 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Meguellati, Kamel published the artcileDNA-Templated Synthesis of Trimethine Cyanine Dyes: A Versatile Fluorogenic Reaction for Sensing G-Quadruplex Formation, Quality Control of 186046-81-1, the publication is Angewandte Chemie, International Edition (2010), 49(15), 2738-2742, S2738/1-S2738/17, database is CAplus and MEDLINE.

The fluorogenic synthesis of a sym. or unsym. trimethine cyanine dye by an aldolization-elimination reaction between two nonfluorescent precursors was applied for sensing G-quadruplex formation in vitro. Two peptide nucleic acids PNAs were designed that can each hybridize in a sequence-specific manner with five nucleobases upstream and five nucleobases downstream of the parallel-stranded ckit21T quadruplex chosen as a model system. They were functionalized at their C-terminal or N-terminal end with either an N-alkyl-2-methyleneindoline (Ind1-3) or an N-alkyl-2-(3,3-dimethylindolin-2-ylidene)acetaldehyde (Aid). Two ε-N,N-dimethyllysine residues per PNA strand were also added to ensure solubility of both PNAs in water at near-physiol. pH.

Angewandte Chemie, International Edition published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, Quality Control of 186046-81-1.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Zhang, Zhaoda published the artcileHeteroditopic Binding of Magnetic Resonance Contrast Agents for Increased Relaxivity, Application In Synthesis of 186046-81-1, the publication is Angewandte Chemie, International Edition (2011), 50(11), 2621-2624, S2621/1-S2621/12, database is CAplus and MEDLINE.

We have shown that the small structural perturbation of incorporating a PNA (peptide nucleic acid) group into a fibrin-targeted contrast agent has a profound impact on relaxivity. The PNA moiety increases mol. weight by 3% but increases relaxivity by 50% compared to Gd2-Gly2-Pep-Gd2. The effect of the PNA group on relaxivity is the equivalent of synthesizing an agent with six GdDTPA moieties to achieve equivalent relaxivity. The PNA group has a modest pos. impact on fibrin binding and serves to rigidify the N-terminal portion of the mol. upon fibrin binding. Importantly, the PNA group does not increase non-specific protein binding. As a result, relaxivity of Gd2-T-Pep-Gd2 bound to fibrin is more than 50% increased compared to Gd2-Pep-Gd2 while the relaxivity of the two compounds in plasma is comparable. This should result in much greater clot blood contrast for Gd2-T-Pep-Gd2.

Angewandte Chemie, International Edition published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C8H8O2, Application In Synthesis of 186046-81-1.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Socher, Elke published the artcileDual fluorophore PNA FIT-probes – extremely responsive and bright hybridization probes for the sensitive detection of DNA and RNA, COA of Formula: C39H35N5O8, the publication is Organic & Biomolecular Chemistry (2012), 10(36), 7363-7371, database is CAplus and MEDLINE.

Fluorescently labeled oligonucleotides are commonly employed as probes to detect specific DNA or RNA sequences in homogeneous solution Useful probes should experience strong increases in fluorescent emission upon hybridization with the target. Dual labeled peptide nucleic acid probes were developed which signal the presence of complementary DNA or RNA by up to 450-fold enhancements of fluorescence intensity. This enabled the very sensitive detection of a DNA target (40 pM LOD), which was detectable at less than 0.1% of the beacon concentration In contrast to existing DNA-based mol. beacons, this PNA-based method does not require a stem sequence to enforce dye-dye communication. Rather, the method relies on the energy transfer between a “smart” thiazole orange (TO) nucleotide, which requires formation of the probe-target complex in order to become fluorescent, and terminally appended acceptor dyes. To improve upon fluorescence responsiveness the energy pathways were dissected. Hydrophobic, spectrally mismatched dye combinations allowed significant (99.97%) decreases of background emission in the absence of a target. By contrast, spectral overlap between TO donor emission and acceptor excitation enabled extremely bright FRET signals. This and the large apparent Stokes shift (82 nm) suggests potential applications in the detection of specific RNA targets in biogenic matrixes without the need of sample pre-processing prior to detection.

Organic & Biomolecular Chemistry published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C12H14IN, COA of Formula: C39H35N5O8.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Novosjolova, Irina published the artcile2-Methoxypyridine as a Thymidine Mimic in Watson-Crick Base Pairs of DNA and PNA: Synthesis, Thermal Stability, and NMR Structural Studies, HPLC of Formula: 186046-81-1, the publication is ChemBioChem (2017), 18(21), 2165-2170, database is CAplus and MEDLINE.

The development of nucleic acid base-pair analogs that use new modes of mol. recognition is important both for fundamental research and practical applications. The goal of this study was to evaluate 2-methoxypyridine as a cationic thymidine mimic in the A-T base pair. The hypothesis was that including protonation in the Watson-Crick base pairing scheme would enhance the thermal stability of the DNA double helix without compromising the sequence selectivity. DNA and peptide nucleic acid (PNA) sequences containing the new 2-methoxypyridine nucleobase (P) were synthesized and studied by using UV thermal melting and NMR spectroscopy. Introduction of P nucleobase caused a loss of thermal stability of ≈10°C in DNA-DNA duplexes and ≈20° C in PNA-DNA duplexes over a range of mildly acidic to neutral pH. Despite the decrease in thermal stability, the NMR structural studies showed that P-A formed the expected protonated base pair at pH 4.3. Our study demonstrates the feasibility of cationic unnatural base pairs; however, future optimization of such analogs will be required.

ChemBioChem published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, HPLC of Formula: 186046-81-1.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Kummer, Susann published the artcileFluorescence imaging of influenza H1N1 mRNA in living infected cells using single-chromophore FIT-PNA, Computed Properties of 186046-81-1, the publication is Angewandte Chemie, International Edition (2011), 50(8), 1931-1934, S1931/1-S1931/22, database is CAplus and MEDLINE.

The FIT-PNA probes used in this work contain a single thiazole orange (TO) intercalator serving as artificial fluorescent nucleobase. These probes respond to changes of the local structure in the vicinity of the dye rather than to the more global changes of conformation that confer fluorescence signaling by dual-labeled mol. beacons. Herein we demonstrate the advantageous properties of FIT-PNA probes in the imaging of mRNA from an influenza virus strain belonging to the same subtype as the recently emerged swine virus (A/Mexico/1/2009, H1N1).

Angewandte Chemie, International Edition published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, Computed Properties of 186046-81-1.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Kummer, Susann published the artcilePNA FIT-Probes for the Dual Color Imaging of Two Viral mRNA Targets in Influenza H1N1 Infected Live Cells, COA of Formula: C39H35N5O8, the publication is Bioconjugate Chemistry (2012), 23(10), 2051-2060, database is CAplus and MEDLINE.

Fluorogenic hybridization probes that allow RNA imaging provide information as to how the synthesis and transport of particular RNA mols. is orchestrated in living cells. The authors explored the peptide nucleic acid (PNA)-based FIT-probes in the simultaneous imaging of two different viral mRNA mols. expressed during the replication cycle of the H1N1 influenza A virus. PNA FIT-probes are non-nucleotidic, nonstructured probes and contain a single asym. cyanine dye which serves as a fluorescent base surrogate. The fluorochrome acts as a local intercalator probe and reports hybridization of target DNA/RNA by enhancement of fluorescence. Though multiplexed hybridization probes are expected to facilitate the anal. of RNA expression, there are no previous reports on the dual color imaging of two different viral mRNA targets. The authors developed a set of two differently colored PNA FIT-probes that allow the spectrally resolved imaging of mRNA coding for neuraminidase (NA) and matrix protein 1 (M1); proteins which execute distinct functions during the replication of the influenza A virus. The probes were characterized by a wide range of applicable hybridization temperatures The same probe sequence enabled live-cell RNA imaging (at 37°) as well as real-time PCR measurements (at 60° annealing temperature). This facilitated a comprehensive anal. of RNA expression by quant. (qPCR) and qual. (imaging) means. Confocal laser scanning microscopy showed that the viral-RNA specific PNA FIT-probes neither stained noninfected cells nor cells infected by a control virus. The joint use of differently colored PNA FIT-probes in this feasibility study revealed significant differences in the expression pattern of influenza H1N1 mRNAs coding for NA or M1. These experiments provide evidence for the usefulness of PNA FIT-probes in studies on the temporal and spatial progression of mRNA synthesis in living cells for two mRNA species.

Bioconjugate Chemistry published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, COA of Formula: C39H35N5O8.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia