Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate

• Eleni Dimitriou and
• Gavin J. Miller

Beilstein J. Org. Chem. 2021, 17, 1527–1532, doi:10.3762/bjoc.17.110

• instance we were able to modify the nucleophile component to O-benzylhydroxylamine and supress unwanted elimination. Unable to do this here, we instead reduced the reaction temperature to 0 °C, maintaining this for 40 minutes. Pleasingly, the yield and product distribution were improved, affording

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

• Premansh Dudhe,
• Mena Asha Krishnan,
• Kratika Yadav,
• Diptendu Roy,
• Krishnan Venkatasubbaiah,
• Biswarup Pathak and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101

• derivative 3ac (10 nM, 100 nM, 1 μM, 10 μM, and 100 μM), the cellular uptake and distribution was monitored by using confocal microscopy (λex = 405 nm; λem range = 420–470 nm). Selected examples of compounds containing the γ-carboline core. Single-crystal XRD structure of 3ac (CCDC: 1897787). UV–vis

• of carboline derivative 3ac in HeLa cells. a) Confocal fluorescent image of HeLa cells after 3 h incubation with 10 μM concentration of 3ac (20-fold magnification, 2-fold zoom); b) DIC image of HeLa cells; c) overlay of (a) and (b) indicating the distribution of 3ac in the cytoplasm with distinct

Antiviral therapy in shrimp through plant virus VLP containing VP28 dsRNA against WSSV

• Santiago Ramos-Carreño,
• Ivone Giffard-Mena,
• Jose N. Zamudio-Ocadiz,
• Alfredo Nuñez-Rivera,
• Ricardo Valencia-Yañez,
• Jaime Ruiz-Garcia,
• Maria Teresa Viana and
• Ruben D. Cadena-Nava

Beilstein J. Org. Chem. 2021, 17, 1360–1373, doi:10.3762/bjoc.17.95

• (pigment red, McCormick4, USA) was administered through the oral cavity using an insulin syringe (BD Micro-FineTM) of 0.5 mL (31G × 6 mm). The distribution of the red-stained solution was observed with a stereoscopic microscope (Labomed, Model CZM6 Trinocular, Stereo Microscope) to determine the time and

• distribution of the product in the digestive tract of the shrimp. After that, two sets of groups in four replicates with five shrimp each. In one of them, 6.0 µg (50 µL) of free dsRNAvp28 was administered, whereas in the second, 50 µL of VLP-dsRNAvp28 (6.0 µg of dsRNAvp28) was applied. After 18 hours both

• . The morphology of the VLPs is maintained after this last step of the assembly process. The VLPs synthesized had two types of morphologies: icosahedral capsids and large rods (Figure 2A, c to f). Also, aggregations of spherical capsid can be observed at the last VLP assembly step. The distribution of

Photoinduced post-modification of graphitic carbon nitride-embedded hydrogels: synthesis of 'hydrophobic hydrogels' and pore substructuring

• Cansu Esen and
• Baris Kumru

Beilstein J. Org. Chem. 2021, 17, 1323–1334, doi:10.3762/bjoc.17.92

• results of HGCM-vTA are exhibiting a sulfur content allocation in accordance with the nitrogen atom distribution in a fair amount of abundance (Figure 2b). Determination of the sulfur content is a facile approval for the surface modification as neither monomers nor g-CN from HGCM are possessing a sulfur

A new glance at the chemosphere of macroalgal–bacterial interactions: In situ profiling of metabolites in symbiosis by mass spectrometry

• Marine Vallet,
• Filip Kaftan,
• Veit Grabe,
• Fatemeh Ghaderiardakani,
• Simona Fenizia,
• Aleš Svatoš,
• Georg Pohnert and
• Thomas Wichard

Beilstein J. Org. Chem. 2021, 17, 1313–1322, doi:10.3762/bjoc.17.91

• macroalgae establish close mutualistic relationships, in which both gain reciprocal benefits forming an ecological unit (holobiont) [1][2][3]. Chemical exchange and physical proximity are the basis of this algae–bacterial mutualism [4], but little is known about the spatial distribution of the bacteria on

• reveal any information on the metabolically active bacteria and the spatial distribution of substances exchanged. While the study of bacterial symbiosis is often limited to either chemistry or microscopy work, recent functional and metabolomics methods are available to enable chemical imaging of

• Information File 1). Even though most of the seawater media was removed from the Ulva samples during sample preparation, crystallisation of seawater salts on the sample surface occurred. The size of the crystals and their distribution within an imaged area were examined using a digital microscope and found to

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

• companies further down the supply chain for formulation, packaging and distribution. International fragrance companies are mainly responsible for the discovery, creation, process development and manufacturing of synthetic fragrance ingredients with all of these representing active areas of current research

• offer the advantage of high surface-to-volume ratio and scalability. These systems consist of nanoparticles embedded into a porous polymer matrix. In heterogeneous catalysis, a higher particle stability and good distribution of the catalyst leads to a reduction in pressure drop alongside a stronger

Synthesis of 10-O-aryl-substituted berberine derivatives by Chan–Evans–Lam coupling and investigation of their DNA-binding properties

• Peter Jonas Wickhorst,
• Mathilda Blachnik,
• Denisa Lagumdzija and
• Heiko Ihmels

Beilstein J. Org. Chem. 2021, 17, 991–1000, doi:10.3762/bjoc.17.81

• the Cu2+-catalyzed coupling reaction with the boronic acid (Scheme 2). The regioselectivity of the latter reaction step is most likely determined by a stronger nucleophilicity of the oxyanion in the 10-position of 6 that is caused by the particular electron distribution in the intermediate 6

Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides

• Roslyn M. Ray,
• Anders Højgaard Hansen,
• Maria Taskova,
• Bernhard Jandl,
• Jonas Hansen,
• Citra Soemardy,
• Kevin V. Morris and
• Kira Astakhova

Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75

• lipid, 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), cholesterol, and PEG-lipid, each with an essential role in the design (Figure 1). These lipids promote the effective distribution of the LNP in vivo as well as aid in effective cargo release from the endosome [1][37]. To this end, we herein

• , USA). Briefly, the scale was set to the scale bar on the image, and the diameter for entire nanoparticles was measured in each image. At least 3 images per LNP formulation were used to determine the size distribution of the LNPs. Data are represented as a box and whisker plot, with min and max values

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

• , multimode microwave reactors for parallel synthesis and multimode microwave reactors for single-batch scale-up. The reactors vary in capacity and the distribution mode of the electromagnetic wave in the reactor vessel. The introduction of the Si–C (silicon–carbon) vials enables high temperature resistance

Valorisation of plastic waste via metal-catalysed depolymerisation

• Francesca Liguori,
• Carmen Moreno-Marrodán and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

• these processes are promoted by heterogeneous acid catalysts (e.g., zeolites, alumina, silica) and are usually unselective, resulting in a broad distribution of gas (C3 and C4 hydrocarbons), liquids (cycloparaffins, oligomers, aromatics) and solid products (char, coke) as a consequence of the random

• in >97% yield into liquid hydrocarbon (alkane) products having a narrow distribution of the molecular weight (960–1130 g⋅mol−1) under 11.7 bar H2 at 300 °C and solvent-free conditions [146]. The pyrolysis oils produced may be used as lubricants, waxes or further processed into detergents and

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

• Marek Kõllo,
• Marje Kasari,
• Villu Kasari,
• Tõnis Pehk,
• Ivar Järving,
• Margus Lopp,
• Arvi Jõers and
• Tõnis Kanger

Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52

• the low solubility of corticosteroids in aqueous solution. The expression of KshA5 and KshB was verified from the cell lysate by polyacrylamide gel electrophoresis and western blotting (see Supporting Information File 1, Figure S1). The product distribution between the cellular pellet and supernatant

A new and efficient methodology for olefin epoxidation catalyzed by supported cobalt nanoparticles

• Lucía Rossi-Fernández,
• Viviana Dorn and
• Gabriel Radivoy

Beilstein J. Org. Chem. 2021, 17, 519–526, doi:10.3762/bjoc.17.46

• , operated at an acceleration voltage of 100 kV. Approximately one hundred metal particles were measured to perform the particle size distribution. The cobalt content in the supported catalyst was determined by inductively coupled plasma atomic emission spectroscopy (ICP-AES), on a Spectro Arcos instrument

• ). The recovered solid catalyst was washed with acetonitrile (3 × 2 mL) and dried in an oven (150 °C, 1 h) for its reuse. TEM micrograph and size distribution graphic for CoNPs@MgO catalyst (scale bar = 20 nm). Plausible mechanistic pathway for olefin epoxidation catalyzed by CoNPs/MgO in the presence of

Synthesis and physicochemical evaluation of fluorinated lipopeptide precursors of ligands for microbubble targeting

• Masayori Hagimori,
• Estefanía E. Mendoza-Ortega and
• Marie Pierre Krafft

Beilstein J. Org. Chem. 2021, 17, 511–518, doi:10.3762/bjoc.17.45

• blood circulation times by allowing them to evade immune detection. PEGs often play a key role in the design of the ligands as a spacer between the nanocarrier surface and the lipid. PEGs have, however, some shortcomings, such as a broad molecular weight distribution, large steric hindrance, and the

• with a Nikon Eclipse 90i microscope (transmission mode, Nikon Instruments Europe, Amsterdam, The Netherlands). A rapid image acquisition was achieved using a Lumenera Infinity 2 charge-coupled device (CCD) camera (Lumenera, Ottawa, Canada). The bubble mean diameter and distribution width after

• ). Optical micrographs and corresponding size distribution of the perfluorohexane-stabilized microbubbles with a shell of a) DPPC, b) DPPC/F-lipopeptide 3, and c) DPPC/hydrocarbon analog 4. Half-lives of microbubbles (25 °C) containing F-lipopeptides 1–3 and hydrocarbon analog 4. a) Schematic representation

Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations

• Vladislav A. Budevich,
• Sergei V. Voitekhovich,
• Alexander V. Zuraev,
• Vadim E. Matulis,
• Vitaly E. Matulis,
• Alexander S. Lyakhov,
• Ludmila S. Ivashkevich and
• Oleg A. Ivashkevich

Beilstein J. Org. Chem. 2021, 17, 385–395, doi:10.3762/bjoc.17.34

• water vs 0.017 Å in n-hexane). Note, that a greater positive τ index indicates a stronger charge separation as a result of the electron transition [36]. Hence, in the case of n-hexane, the distribution of the positive and negative charge is almost not separated, and the CT is small. However, for the

• water solution, the distribution of the positive and negative charge is significantly separated due to a strong CT. Considering that in polar media the S0→S1 electron excitation corresponds to the n→π* transition, leading to a significant CT from the =N5–H group to the tetrazole ring, we can explain the

Annulation of a 1,3-dithiole ring to a sterically hindered o-quinone core. Novel ditopic redox-active ligands

• Sergey V. Norkov,
• Anton V. Cherkasov,
• Andrey S. Shavyrin,
• Maxim V. Arsenyev,
• Viacheslav A. Kuropatov and
• Vladimir K. Cherkasov

Beilstein J. Org. Chem. 2021, 17, 273–282, doi:10.3762/bjoc.17.26

• mixture. X-ray diffraction data revealed that the bond lengths distribution in the six-membered ring of 6b is typical of sterically hindered o-quinones. The annulated fragment including the 1,3-dithiole cycle and the malononitrile unit is almost flat. The six-membered o-quinone ring is distorted due to

• -quinone 4. Each o-quinone molecule bridges two adjacent sodium ions. The bond lengths distribution in the o-quinone moiety in 8 is typical of sterically hindered o-quinones (Table S1 in Supporting Information File 1). According to 1H and 13C NMR spectroscopy data, adduct 8 in CD3OD solution exists as

• -Semiquinones are often used as convenient spin labels to determine the spatial arrangement of ligands and to monitor the processes in the coordination sphere of metal ions in real time [42][43][44][45][46]. The spin density distribution and thus the hyperfine coupling constants for the magnetic nuclei at the

The preparation and properties of 1,1-difluorocyclopropane derivatives

• Kymbat S. Adekenova,
• Peter B. Wyatt and
• Sergazy M. Adekenov

Beilstein J. Org. Chem. 2021, 17, 245–272, doi:10.3762/bjoc.17.25

• it can profoundly modify the physicochemical properties of the parent molecules. In biologically active materials fluorine substituents can affect the charge distribution, electrostatic surface, and solubility of chemical entities, thus often leading to useful outcomes. Incorporating a fluorine group

Exploring the possibility of using fluorine-involved non-conjugated electron-withdrawing groups for thermally activated delayed fluorescence emitters by TD-DFT calculation

• Dongyang Chen and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2021, 17, 210–223, doi:10.3762/bjoc.17.21

• -containing emitters 2CzCF3, 2CzOCF3, 2CzSCF3, and 2CzSF5. The HOMOs in these compounds are mainly located on the two carbazole moieties and a small part on the bridging central benzene ring. The LUMOs of 2CzCF3, 2CzSCF3, and 2CzSF5 are mainly located on the benzene ring and a small distribution onto the

• (4.06 eV), and 2CzBP (3.93 eV) are all significantly smaller compared to those of 2CzCF3, 2CzOCF3, 2CzSCF3, and 2CzSF5. The emissive S1 state for the seven Type I molecules is characterized mainly by a HOMO to LUMO transition, while the distribution of highest occupied natural transition orbitals

• for the Type II emitters are shown in Figure 7 and Figure 8. The HOMOs of 5CzCF3, 5CzOCF3, and 5CzSCF3 are mainly located on the carbazole moieties located ortho and meta to the acceptor group, with only a small distribution on the para-carbazole. For 5CzSF5, the HOMO is evenly distributed over the

Multiswitchable photoacid–hydroxyflavylium–polyelectrolyte nano-assemblies

• Alexander Zika and
• Franziska Gröhn

Beilstein J. Org. Chem. 2021, 17, 166–185, doi:10.3762/bjoc.17.17

• strength may be understood based on the molecular parameters of the building blocks and in particular the polar surface area (PSA), which relates to the three-dimensional charge distribution of the molecule. The PSA results from the area of the polar groups in the molecule taking into account the

• electric field autocorrelation function g1(τ). By a regularized inverse Laplace transformation, the electric field autocorrelation function g1(τ) was transformed into the distribution of relaxation times A(τ). The apparent diffusion coefficients Dapp were calculated by Equation 3 The diffusion coefficients

• nano-assemblies for cycle I (a) and cycle II (b). Dynamic light scattering: Electric field autocorrelation function g1(τ) and distribution of relaxation times A(τ) at a scattering angle of θ = 90° for cycle I (a) and cycle II (b,c). Cycle II is separated for better distinguishability: b) the states A

Novel library synthesis of 3,4-disubstituted pyridin-2(1H)-ones via cleavage of pyridine-2-oxy-7-azabenzotriazole ethers under ionic hydrogenation conditions at room temperature

• Romain Pierre,
• Anne Brethon,
• Sylvain A. Jacques,
• Aurélie Blond,
• Sandrine Chambon,
• Sandrine Talano,
• Catherine Raffin,
• Branislav Musicki,
• Claire Bouix-Peter,
• Loic Tomas,
• Gilles Ouvry,
• Rémy Morgentin,
• Laurent F. Hennequin and
• Craig S. Harris

Beilstein J. Org. Chem. 2021, 17, 156–165, doi:10.3762/bjoc.17.16

• (Table 3, entry 5). To decrease reaction times further, we carried out the reaction in neat TFA/TES mixture (4:1 v/v, 5 volumes) and obtained a 62% conversion at just rt after 24 h (Table 3, entry 6). The product distribution was even further improved by addition of water to the reaction mixture to avoid

Insight into functionalized-macrocycles-guided supramolecular photocatalysis

• Minzan Zuo,
• Krishnasamy Velmurugan,
• Kaiya Wang,
• Xueqi Tian and
• Xiao-Yu Hu

Beilstein J. Org. Chem. 2021, 17, 139–155, doi:10.3762/bjoc.17.15

• a stabilizer to control the size and distribution of the NPs and are able to intensely regulate the photocatalytic performance. 5) To improve the sustainability, noble metals need to be replaced by earth-abundant metals. However, in most cases, earth-abundant metals have a lower photocatalytic

Control over size, shape, and photonics of self-assembled organic nanocrystals

• Chen Shahar,
• Yaron Tidhar,
• Yunmin Jung,
• Haim Weissman,
• Sidney R. Cohen,
• Ronit Bitton,
• Iddo Pinkas,
• Gilad Haran and
• Boris Rybtchinski

Beilstein J. Org. Chem. 2021, 17, 42–51, doi:10.3762/bjoc.17.5

• , Supporting Information File 1) are less homogeneous and demonstrate a larger size distribution than the crystals obtained by exerting control through the THF content. In order to gain insight into the crystallization mechanism and the effect of the THF concentration on the crystallization process, we

Molecular basis for protein–protein interactions

• Brandon Charles Seychell and
• Tobias Beck

Beilstein J. Org. Chem. 2021, 17, 1–10, doi:10.3762/bjoc.17.1

• effect is termed the desalting effect [52] and is comparable to desolvation. This effect is also dependent on the charge–charge interactions of the complex as different charges might alter the ion distribution in the solvent, changing the ion interactions. On the other hand, an example of the ionic

Secondary metabolites of Bacillus subtilis impact the assembly of soil-derived semisynthetic bacterial communities

• Heiko T. Kiesewalter,
• Carlos N. Lozano-Andrade,
• Mikael L. Strube and
• Ákos T. Kovács

Beilstein J. Org. Chem. 2020, 16, 2983–2998, doi:10.3762/bjoc.16.248

• prolonged incubation. The B. subtilis strains were added at a community assembly phase when Bacillus was the dominating genus, so that the general genera distribution was not expected to be influenced extensively. Nevertheless, after 48 h cocultivation, the final relative abundance of the Bacillus genus was

A novel and robust heterogeneous Cu catalyst using modified lignosulfonate as support for the synthesis of nitrogen-containing heterocycles

• Bingbing Lai,
• Meng Ye,
• Ping Liu,
• Minghao Li,
• Rongxian Bai and
• Yanlong Gu

Beilstein J. Org. Chem. 2020, 16, 2888–2902, doi:10.3762/bjoc.16.238

• the results are presented in Figure 4. The LS-FAS-Cu catalyst featured irregular and blocky morphology with uneven size from 100 nm to 400 nm (Figure 4a–d). In addition, the elemental mapping images clearly revealed the presence and uniform distribution of C, Cu, O, and S in LAS-FAS-Cu. XPS was

Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system

• David Liese,
• Hans Henning Wenk,
• Xin Lu,
• Jochen Kleinen and
• Gebhard Haberhauer

Beilstein J. Org. Chem. 2020, 16, 2820–2830, doi:10.3762/bjoc.16.232

• rare case where no primer is needed for the formation of RWLM. To our knowledge, there is only one other example of a binary system with such a behavior [59]. Moreover, the surfactant, that was used as a precursor exhibits a certain distribution of the molecular weight but still was able to form