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Search for "hybridization" in Full Text gives 69 result(s) in Beilstein Journal of Organic Chemistry.
A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices
Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122
- . Additionally, transient PL decay spectra of TPECNz in solvents of different polarities showed a single exponential decay in nanosecond ranges (Figure 3c), signifying that the excited state responsible for the PL emission originates from the hybridization between LE and CT excited states or HLCT state, not a
Exploring the role of halogen bonding in iodonium ylides: insights into unexpected reactivity and reaction control
Beilstein J. Org. Chem. 2023, 19, 1171–1190, doi:10.3762/bjoc.19.86
- strength of a σ-hole typically increases with polarizability within the same group (I > Br > Cl >> F) [41][46][47]; however, the electron attracting abilities of the host [31][46], the electronegativity of the halogen atom [41] and, the degree of spn-hybridization in the covalent σR–X bond can also
CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview
Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29
- ascorbate in DMSO (Scheme 9). According to UV–vis and circular dichroism (CD) spectrum measurements, the authors state that the formation of the dimer of porphyrin 50 can be attributed to DNA hybridization and through-space electronic interactions. In this investigation, it was found that the DNA serves as
Total synthesis of insect sex pheromones: recent improvements based on iron-mediated cross-coupling chemistry
Beilstein J. Org. Chem. 2023, 19, 158–166, doi:10.3762/bjoc.19.15
- efficiently applied at large industrial scales. Extension of such methods to more challenging hybridization patterns in cross-coupling chemistry applied to synthesis of other insect pheromones is currently investigated in our groups. Structure of the (8E,10Z)-tetradecadienal (1, sex pheromone of the horse
Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr4/PPh3 and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior
Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9
- studies, one of us (M. R. E. A.) felt intrigued by the potential of chemical hybridization of cholesterol through simple connections of pharmacophores including sugars, chalcones, quinolone, theophylline, and ferrocene using click chemistry [9][10][11]. Following this strategy, cholesterol was
Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes
Beilstein J. Org. Chem. 2022, 18, 1338–1345, doi:10.3762/bjoc.18.139
- objects of growing interest in the fields of coordination chemistry [3][4][5] and asymmetric catalysis [6][7]. Due to the sp2-hybridization of the phosphorus atom, phosphaferrocenes are commonly regarded as phosphorus ligands with weaker σ-donor character than classical tertiary phosphines and stronger π
Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment
Beilstein J. Org. Chem. 2022, 18, 631–638, doi:10.3762/bjoc.18.63
- 27272, Sharjah, United Arab Emirates The Regional Center for Mycology and Biotechnology, Al-Azhar University, Nasr City, Cairo, 11371, Egypt Department of Chemistry, The University of Jordan, Amman 11942, Jordan 10.3762/bjoc.18.63 Abstract A new chemical library based on the hybridization of cholic
- chemical library based on the hybridization of cholic acid with the heterocyclic moiety 1,3,4-oxadizole was synthesized. All new compounds were unambiguously characterized by various spectroscopic techniques. The newly synthesized compounds were assessed in vitro for their antimicrobial activities
Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin imines
Beilstein J. Org. Chem. 2022, 18, 303–308, doi:10.3762/bjoc.18.34
- oxindoles [7][8][9][10][11] and also of aminoboronic acids [12], we recently exploited a molecular hybridization strategy to synthesize chiral oxindole-based β-aminoboronic acids and spiro derivatives [13]. Apart from our work and a quite recent report describing a useful Cu-catalyzed enantioselective
Cationic oligonucleotide derivatives and conjugates: A favorable approach for enhanced DNA and RNA targeting oligonucleotides
Beilstein J. Org. Chem. 2021, 17, 1828–1848, doi:10.3762/bjoc.17.125
- unmodified PS-ASO [43]. It is important to notice that C-5 modifications, besides resulting in improved nuclease stability and providing improved target hybridization, allow for activation of RNase H. This was demonstrated by Matsuda and co-workers when they incorporated modification 2 or 3 into a 17-mer ON
- better hybridization properties than LNA-thymidine; however, only modification 22 gave significant increases in Tm relative to modification 19 used as control. This finding was ascribed to both the extended π-conjugation of the alkynyl-functionalized nucleobase and stabilizing electrostatic interactions
- effects of different amine-functionalized groups. Beginning with the 2’-O-alkylated RNA nucleotides (Table 4) it has been shown that the introduction of an aminopropyl group via 2’-O-alkylation (modification 34) leads to moderately improved hybridization properties for the modified ON against its RNA
Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications
Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116
- involving PNA usually follow the order PNA–PNA > PNA–RNA > PNA–DNA [20][21]. Hybridization of PNA with complementary nucleic acids is enthalpy driven, involving large favorable gains in enthalpy compensated by significant unfavorable entropy, as typically observed for nucleic acid complexes [22]. The
- greatly improved cellular uptake of γ-GPNA. Others have also investigated positively charged α- and γ-modifications of the PNA backbone, and most of them showed promising hybridization properties and improved cellular uptake [82][83][84][85][86]. Very recent work has used α- and γ-positions of the PNA
- functionalities have been introduced in PNA to improve water solubility and better mimic DNA/RNA structure. One of the early studies was on chimeras of PNA and phosphono-PNA (Figure 5) that improved water solubility and in some cases resulted in stronger hybridization with complementary DNA and RNA [90]. The
Double-headed nucleosides: Synthesis and applications
Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98
- complementary base pairs was monitored by UV melting curve analysis [33]. Hybridization data revealed that the synthesized double-headed nucleotide recognized itself either through formation of Watson–Crick base pairs with two complementary adenosines or through the formation of T:T (thymine:thymine) base pairs
- then incorporated into oligonucleotide sequences, followed by thermal hybridization studies that indicated that the 5′-(S)-C-position is ideal for placing an additional nucleobase in the minor groove and interstrand stacking effects decreased with an increase in the length of the linker [31][65
Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications
Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76
- attributes, nuclease stability, and hybridization to single and double stranded nucleic acid targets have led to studies to investigate 3'-NP DNA for antisense and antigene purposes. For example, as an antisense agent in the treatment of human leukemia [67], as an inhibitor of transcription elongation
- 7D) monomer which has been shown to stabilize oligonucleotides similarly to unmodified LNA with a nuclease resistance greater than PS-modified oligonucleotides [157]. Incorporation of selenium at C2' in a thymine-bearing LNA nucleoside (Figure 7E) has been demonstrated to have a hybridization ability
- ]. Hybridization studies of uniformly modified ANA of mixed nucleobase composition to complementary RNA revealed reduced thermal stability relative to the corresponding DNA/RNA duplex by approximately 1.5 °C per modification [182][183]. A significant reduction in stability of the duplex was observed in the binding
Selective synthesis of α-organylthio esters and α-organylthio ketones from β-keto esters and sodium S-organyl sulfurothioates under basic conditions
Beilstein J. Org. Chem. 2021, 17, 234–244, doi:10.3762/bjoc.17.24
- (3n) in 70% yield (Table 2, entry 14). We also noted that the hybridization of the adjacent carbon atom bonded to the ester group had a direct effect on the formation of the product 3. For instance, comparing entry 1 with entries 15 and 16 in Table 2, we observed a sudden decrease in the reaction
Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups
Beilstein J. Org. Chem. 2020, 16, 2141–2150, doi:10.3762/bjoc.16.182
- to the hybridization state of cyclopropyl carbon atoms. However, β-fluorination of the oxetanyl derivative F1 led to a lipophilicity increase. With the caveat that the value for F1 is not a measured value and the difference is well within the standard deviation (0.23 logP units), this increase is in
Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis
Beilstein J. Org. Chem. 2020, 16, 1163–1187, doi:10.3762/bjoc.16.103
- classes depending on the nitrogen atom hybridization and the substitution of the N atom, including iminyl, amidyl, aminyl, and aminium units (Scheme 26). The reactivity depends on the philicity of each species. In a general manner, NCRs are prone to the addition to unsaturated systems, either inter- or
A smart deoxyribozyme-based fluorescent sensor for in vitro detection of androgen receptor mRNA
Beilstein J. Org. Chem. 2020, 16, 1135–1141, doi:10.3762/bjoc.16.100
- aptamer module. This solves a problem of secondary structure in hybridization with the target sequence of full-length mRNA. It was shown that within 24 hours the proposed sensor specifically recognized both a synthetic 60-nucleotide RNA fragment (LOD is 1.4 nM of RNA fragment at 37 °C) and a full-sized
- , deoxyribozyme-based biosensors [5], and aptamer-based biosensors [3]. The detection mainly relies on a specific hybridization between a well-known target fragment and the biosensor strands. To increase selectivity NAs are also created as binary or split construction. Due to the simplicity, the DNA hybridization
- assembling was evaluated using agarose gel electrophoresis (Figure 1E). The single band proved that in the chosen conditions there was a complete hybridization of all 5 strands into an integrated SDFS complex. After hybridization between SDFS and 60-AR_RNA we expected to see a specific cleavage of target
Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore
Beilstein J. Org. Chem. 2020, 16, 1111–1123, doi:10.3762/bjoc.16.98
- )=C bond disappeared and two new signals appeared at around 68–69 ppm (quaternary C) and 51–60 ppm (CH). These facts are consistent with the expected hybridization change from Csp2 to Csp3 after formation of the cyclobutane ring. Determination of the crystal structure of complex 4a, which is shown in
Towards triptycene functionalization and triptycene-linked porphyrin arrays
Beilstein J. Org. Chem. 2020, 16, 763–777, doi:10.3762/bjoc.16.70
- , owing to electron transfer from the zinc porphyrin unit to the nickel porphyrin unit. Initial studies have shown the promise of triptycene as a linker for electron transfer studies, and an expanded library could lead to further interesting results where the linearity, hybridization and accessibility of
Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties
Beilstein J. Org. Chem. 2020, 16, 587–595, doi:10.3762/bjoc.16.53
- nodal plane near the 1,7-positions in the HOMO and smaller MO coefficients at the 2,6-positions than those at the 3,5-positions. Rather, a stabilization of the LUMO energies is found in 5a and 6a even though the MO hybridization of the BODIPY core with π-orbitals of ethynyl moieties is less affected
Architecture and synthesis of P,N-heterocyclic phosphine ligands
Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35
- . The π-acceptor character of phosphorus can be reinforced by the presence of oxygen and/or nitrogen whilst σ-donating potency of nitrogen can be manipulated by switching between sp3 and sp2 hybridization [9][49][50]. The synthesis of phosphines is quite delicate because when exposed to air, some of
Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides
Beilstein J. Org. Chem. 2020, 16, 60–70, doi:10.3762/bjoc.16.8
- major groove recognition [21][22]. Woolley et al. reported other photoisomerizable Tf mimetics that interacted through the major groove [23][24]. Hybridization of DNA [25][26][27] or PNA/DNA [28] can be light-controlled by azobenzene-modified DNA. While DNA covalently modified with azobenzene moieties
Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction
Beilstein J. Org. Chem. 2020, 16, 1–8, doi:10.3762/bjoc.16.1
- carbon monoxide-releasing properties [27][28] of dicobalt hexacarbonyl alkyne complexes have been noted, and their medicinal potential has been summarized [29][30][31]. Despite developments, the collection of metallo-nucleosides is limited. Hybridization of alkyl and aryl-substituted alkyne cobalt
Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence
Beilstein J. Org. Chem. 2019, 15, 2612–2622, doi:10.3762/bjoc.15.254
- advantageous photophysical properties that include spectrally tunable and highly intense fluorescence [1][2]. On the one hand, those compounds that contain the boron atom in a valence-saturated situation corresponding to sp3 hybridization (such as Bodipy dyes [3][4], N,C-chelate organoboron dyes [5][6][7][8][9
- , boron with sp2 hybridization, such as in triarylboranes, offers the possibility to modulate fluorescence properties by the addition of Lewis bases (e.g., fluoride ions [27][28][29][30][31]) or by exploring the electron-accepting properties of the boron, including charge-transfer and photoinduced
- observed. The formation of the fluoroboronate complexes was corroborated by the detection of the corresponding mass peaks (see Supporting Information File 1). In addition, 11B NMR spectra, for the example of dye 17, reveal that the boron changes from sp2 to sp3 hybridization on addition of 1 equiv F−; i.e
In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization
Beilstein J. Org. Chem. 2019, 15, 2500–2508, doi:10.3762/bjoc.15.243
- tetra-ortho-fluoroazobenzene–PNA conjugates have promising properties (fast reversible isomerization, exceptional thermal stability, high isomer conversions and sensitivity to visible-light irradiation) as reversible modulators to control oligonucleotide hybridization in biological contexts. Furthermore
- , we verified that this switchable modification delivers a slightly different hybridization behavior in the PNA. Thus, both melting experiments and strand-displacement assays showed that in all the cases the trans-isomer is the one with superior binding affinities. Alternative versions, inspired by our
- hybridization has demonstrated an enormous potential to regulate on-demand biological responses such as gene expression [1]. There are indeed a number of successful examples based on photocaged strategies [2][3][4][5], in which modified nucleic acids interfere irreversibly with gene expression in vitro [6][7
Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids
Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237
- prospect of the tetrazole hybridization strategy in drug discovery. Among the most versatile methods for obtaining tetrazoles are the Ugi-azide four-component reaction (Ugi-azide-4CR) [14][15][16] and the 1,3-dipolar cycloaddition of azides with (acyl)cyanides [17][18]. The Ugi-azide-4CR enables the
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