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Titanium tetrafluoride catalysis for the dehydrative conversion of diphenylmethanols to symmetric and unsymmetric ethers† † Electronic supplementary information (ESI) available: Optimization details, experimental procedures, product characterization, and 1H, 13C, and 19F NMR spectra of products. See DOI: https://doi.org/10.1039/d4ra04712e

ABSTRACT:

SUBMITTER: Singh A

PROVIDER: S-EPMC11296350 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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α-Amino bicycloalkylation through organophotoredox catalysis† † Electronic supplementary information (ESI) available: Experimental procedures, computational details, copies of 1H and 13C NMR spectra. See DOI: https://doi.org/10.1039/d4sc01368a

Project description: Not available

| S-EPMC11253163 | biostudies-literature

Investigation on the Anticancer Activity of Symmetric and Unsymmetric Cyclic Sulfamides.

Project description:The sulfamide functional group has been extensively employed in organic synthesis to discover probes and drugs in various applications such as cancer, human immunodeficiency virus (HIV), virus, and diabetes. Herein, we describe the synthesis of 7-membered symmetric and unsymmetric sulfamide compounds and their biological evaluation through the National Cancer Institute (NCI) panel of 60 human tumor cell lines (NCI-60) and the mechanism of action study. The results of a study from the NCI-60 cell line exhibited that many synthesized cyclic sulfamide compounds inhibited breast cancer (MDA-MB-468). The mechanism of action study of a representative compound 18 showed the inhibition of proliferation and apoptosis in A549 lung cancer cells.

| S-EPMC7883376 | biostudies-literature

Hidden hydrophobicity impacts polymer immunogenicity† † Electronic supplementary information (ESI) available: Experimental details and supplementary figures. See DOI: https://doi.org/10.1039/d2sc07047b

Project description:Antibodies against poly(ethylene glycol) (PEG) have been found to be the culprit of side reactions and efficacy loss of a number of PEGylated drugs. Fundamental mechanisms of PEG immunogenicity and design principles for PEG alternatives still have not been fully explored. By using hydrophobic interaction chromatography (HIC) under varied salt conditions, we reveal the “hidden” hydrophobicity of those polymers which are generally considered as hydrophilic. A correlation between the hidden hydrophobicity of a polymer and its polymer immunogenicity is observed when this polymer is conjugated with an immunogenic protein. Such a correlation of hidden hydrophobicity vs. immunogenicity for a polymer also applies to corresponding polymer–protein conjugates. Atomistic molecular dynamics (MD) simulation results show a similar trend. Based on polyzwitterion modification and with this HIC technique, we are able to produce extremely low-immunogenic protein conjugates as their hydrophilicity is pushed to the limit and their hydrophobicity is eliminated, breaking the current barriers of eliminating anti-drug and anti-polymer antibodies. The hidden hydrophobicity of conventional polymers widely considered as hydrophilic is closely related to their immunogenicity when they are conjugated to immunogenic proteins.

| S-EPMC9945064 | biostudies-literature

s-Block metal complexes of superbulky (tBu3Si)2N−: a new weakly coordinating anion?† † Electronic supplementary information (ESI) available: Experimental details, 1H and 13C NMR spectra, crystallographic details including ORTEP presentations, details for the DFT calculations including XYZ-files. CCDC 2321294–2321305. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d3sc06896j

Project description: Not available

| S-EPMC10952107 | biostudies-literature

Sulfur(iv) reagents for the SuFEx-based synthesis of substituted sulfamate esters† † Electronic supplementary information (ESI) available: Experimental procedures, methods, and optimization data; NMR, IR, HPLC and MS data including 1H, 13C, and 19F NMR spectra. See DOI: https://doi.org/10.1039/d2sc05945b

Project description:Sulfur(vi) fluoride exchange chemistry has been reported to be effective at synthesizing valuable sulfur(vi) functionalities through sequential nucleophilic additions, yet oxygen-based nucleophiles are limited in this approach to phenolic derivatives. Herein, we report a new sulfur(iv) fluoride exchange strategy to access synthetically challenging substituted sulfamate esters from alkyl alcohols and amines. We also report the development of a non-gaseous, sulfur(iv) fluoride exchange reagent, N-methylimidazolium sulfinyl fluoride hexafluorophosphate (MISF). By leveraging the reactivity of the sulfur(iv) center of this novel reagent, the sequential addition of alcohols and amines to MISF followed by oxidation afforded the desired substituted sulfamates in 40–83% yields after two steps. This new strategy expands the scope of SuFEx chemistry by increasing the accessibility of underdeveloped –S(O)F intermediates for future explorations. N-Methylimidazolium sulfinyl fluoride hexafluorophosphate (MISF) was developed as a solution-stable sulfur(iv) reagent to access substituted sulfamate esters using a sulfur(iv) fluoride exchange strategy.

| S-EPMC9930924 | biostudies-literature

Carpe diene! Europium-catalyzed [3,3] and [5,5] rearrangements of aryl-pentadienyl ethers† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d3ra05641d

Project description: Not available

| S-EPMC10618941 | biostudies-literature

Catalytic photochemical enantioselective α-alkylation with pyridinium salts† † Electronic supplementary information (ESI) available: Experimental details, characterization data, and spectral data (PDF). See DOI: https://doi.org/10.1039/d2sc05654b

Project description:We have developed a chiral amine catalyzed enantioselective α-alkylation of aldehydes with amino acid derived pyridinium salts as alkylating reagents. The reaction proceeds in the presence of visible light and in the absence of a photocatalyst via a light activated charge-transfer complex. We apply this photochemical stereoconvergent process to the total synthesis of the lignan natural products (−)-enterolactone and (−)-enterodiol. Mechanistic studies support the ground-state complexation of the reactive components followed by divergent charge-transfer processes involving catalyst-controlled radical chain and in-cage radical combination steps. We have developed a chiral amine catalyzed enantioselective α-alkylation of aldehydes with amino acid derived pyridinium salts as alkylating reagents.

| S-EPMC9847668 | biostudies-literature

Solution NMR readily reveals distinct structural folds and interactions in doubly 13C- and 19F-labeled RNAs.

Project description:RNAs form critical components of biological processes implicated in human diseases, making them attractive for small-molecule therapeutics. Expanding the sites accessible to nuclear magnetic resonance (NMR) spectroscopy will provide atomic-level insights into RNA interactions. Here, we present an efficient strategy to introduce 19F-13C spin pairs into RNA by using a 5-fluorouridine-5'-triphosphate and T7 RNA polymerase-based in vitro transcription. Incorporating the 19F-13C label in two model RNAs produces linewidths that are twice as sharp as the commonly used 1H-13C spin pair. Furthermore, the high sensitivity of the 19F nucleus allows for clear delineation of helical and nonhelical regions as well as GU wobble and Watson-Crick base pairs. Last, the 19F-13C label enables rapid identification of a small-molecule binding pocket within human hepatitis B virus encapsidation signal epsilon (hHBV ε) RNA. We anticipate that the methods described herein will expand the size limitations of RNA NMR and aid with RNA-drug discovery efforts.

| S-EPMC7541061 | biostudies-literature

13C/15N-19F intermolecular REDOR NMR study of the interaction of TAR RNA with Tat peptides.

Project description:The complex of the HIV TAR RNA with the viral regulatory protein Tat is of considerable interest, but the plasticity of this interaction has made it impossible so far to establish the structure of that complex. In order to explore a new approach to obtain structural information on protein-RNA complexes, we performed (13)C/(15)N-(19)F REDOR NMR experiments in the solid state on TAR bound to a peptide comprising the RNA-binding section of Tat. A critical arginine in the peptide was uniformly (13)C and (15)N labeled, and 5-fluorouridine was incorporated at the U23 position of TAR. REDOR irradiation resulted in dephasing of the (13)C and (15)N resonances, indicating the proximity of the U23(5F)-C and U23(5F)-N spin pairs. Best fits to the REDOR data show the U23(5F)-C distances and the U23(5F)-N distances are in good agreement with the distances obtained from solution NMR structures of partial complexes of Tat with TAR. These results demonstrate that it is possible to study protein-RNA complexes using solid-state REDOR NMR measurements, adding to a growing list of solid state techniques for studying protein-nucleic acid complexes.

| S-EPMC3238802 | biostudies-literature

A theory-driven synthesis of symmetric and unsymmetric 1,2-bis(diphenylphosphino)ethane analogues via radical difunctionalization of ethylene.

Project description:1,2-Bis(diphenylphosphino)ethane (DPPE) and its synthetic analogues are important structural motifs in organic synthesis, particularly as diphosphine ligands with a C2-alkyl-linker chain. Since DPPE is known to bind to many metal centers in a bidentate fashion to stabilize the corresponding metal complex via the chelation effect originating from its entropic advantage over monodentate ligands, it is often used in transition-metal-catalyzed transformations. Symmetric DPPE derivatives (Ar12P-CH2-CH2-PAr12) are well-known and readily prepared, but electronically and sterically unsymmetric DPPE (Ar12P-CH2-CH2-PAr22; Ar1≠Ar2) ligands have been less explored, mostly due to the difficulties associated with their preparation. Here we report a synthetic method for both symmetric and unsymmetric DPPEs via radical difunctionalization of ethylene, a fundamental C2 unit, with two phosphine-centered radicals, which is guided by the computational analysis with the artificial force induced reaction (AFIR) method, a quantum chemical calculation-based automated reaction path search tool. The obtained unsymmetric DPPE ligands can coordinate to several transition-metal salts to form the corresponding complexes, one of which exhibits distinctly different characteristics than the corresponding symmetric DPPE-metal complex.

| S-EPMC9678890 | biostudies-literature

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