SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes

• Julien Borrel and
• Jerome Waser

Beilstein J. Org. Chem. 2024, 20, 701–713, doi:10.3762/bjoc.20.64

• DME also allowed solubilization. The solubilization due to residual water coming from the alkynyl-BF3K was ruled out by careful drying of 5a. We postulated that an ion exchange between Ru(bpy)3Cl2 and 5a can occur to afford a more soluble photocatalyst with the general formula 9 (Scheme 2C

• ). Interestingly, when the solubilization experiment was carried out with the tetrabutylammonium salt 7 only moderate solubilization occurred (Scheme 2B), which could explain the lower yield previously observed (Scheme 2A). Neutral TMS-alkyne 8 cannot be involved in ion exchange and therefore this could be one of

• was used with alkyl-substituted alkynyl-BF3K, probably due to the poor solubilization of the catalyst. Finally, control experiments in the absence of photocatalyst or light only afforded traces of product (Table 8, entry 7). The successful scope of the reaction was already described in our previous

Facile access to pyridinium-based bent aromatic amphiphiles: nonionic surface modification of nanocarbons in water

• Lorenzo Catti,
• Shinji Aoyama and
• Michito Yoshizawa

Beilstein J. Org. Chem. 2024, 20, 32–40, doi:10.3762/bjoc.20.5

• Lorenzo Catti Shinji Aoyama Michito Yoshizawa Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan 10.3762/bjoc.20.5 Abstract Efficient water-solubilization of nanocarbons is desirable for

• )2–Y (Y = OCH3, OH, and imidazole)). The new amphiphiles quantitatively self-assemble into ≈2 nm-sized aromatic micelles in water independent of the side-chain. Importantly, efficient water-solubilization and nonionic surface modification of various nanocarbons (e.g., fullerene C60, carbon nanotubes

• , and graphene nanoplatelets) are achieved through noncovalent encircling with the bent amphiphiles. The resultant imidazole-modified nanocarbons display a pH-responsive surface charge, as evidenced by NMR and zeta-potential measurements. In addition, solubilization of a nitrogen-doped nanocarbon (i.e

Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

• Ghenwa Nasr,
• Hélène Greige-Gerges,
• Sophie Fourmentin,
• Abdelhamid Elaissari and
• Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

• can subsequently achieve the highest solubilization of CHOL [27], while the low-substituted derivatives (CRYSMEB in our case) were less cytotoxic and maintained the integrity of endothelial cells assuming a lower affinity to CHOL membrane compared to the other derivatives [23]. Furthermore, the

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• porphyrin 174 and stirred at room temperature for 24 h, solubilization occurred, resulting in a homogeneous solution. This is due to the formation of a supramolecular assembly in which the hydrophobic adamantane arms of 176b are sequestered by the β-CD arms of porphyrin 174, resulting in water solubility

Preparation of β-cyclodextrin/polysaccharide foams using saponin

• Max Petitjean and
• José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

• be observable at different heights in the graduated cylinder. Several interaction processes can influence the viscosity behaviour of these mixtures and have an impact on their stability. For instance, when considering mixtures of chitosan with saponin, the possibility of solubilization of chitosan

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

• Konstantin Lebedinskiy,
• Volodymyr Lobaz and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

• better effectiveness than other tested supramolecular hosts. Keywords: cyclodextrin; dimer; methylation; solubilization; tetracene; Introduction Cyclodextrins (CDs) are cyclic oligomers of glucose that play an important role in supramolecular chemistry [1]. The structure of any CD contains a

• pentacene and other larger linear acenes if we would achieve some success with it. In this work, we report on the efficient synthesis of new cyclodextrin supramolecular hosts based on selectively methylated β-CD derivatives and their dimers; moreover, we compare their effectiveness in the solubilization of

• . Especially it concerned the dimers whose solutions were approximately two times less concentrated than others. However, we decided from the practical point of view that the effectiveness of the solubilization effect should be calculated to the host's mass rather than its molar concentration. The UV

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

• Luke O. Jones,
• Leah Williams,
• Tasmin Boam,
• Martin Kalmet,
• Chidubem Oguike and
• Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

• polymers, such as PDMAPS and its structural analogues [88][89][90][91], and on the other hand, polymers with strong hydrogen acceptor and donor units, like the uncharged PNAGA [92][93][94][95][96], show a pronounced UCST. In contrast, the solubilization process of a polymer with LCST behavior is an

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

• Tania Xavier,
• Sylvie Condon,
• Christophe Pichon,
• Erwan Le Gall and
• Marc Presset

Beilstein J. Org. Chem. 2021, 17, 2085–2094, doi:10.3762/bjoc.17.135

• with complete conversion, the isolation of the pure product was less straightforward and required a recrystallization from a methanol/water mixture, leading to a moderate yield (56%) due to a partial solubilization of the product 7h. This complication was yet balanced by the practicality of the second

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

¹⁹F NMR as a tool in chemical biology

• Diana Gimenez,
• Aoife Phelan,
• Cormac D. Murphy and
• Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

• ionization and ion mobility), CD spectroscopy and atomic force microscopy, the authors were able to obtain detailed information about the size and secondary structure associated with some of the soluble intermediates. These included: large β-sheet oligomers formed immediately after solubilization (oligomer

The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY

• Patrizia Andreozzi,
• Lorenza Tamberi,
• Elisamaria Tasca,
• Gina Elena Giacomazzo,
• Marta Martinez,
• Mirko Severi,
• Marco Marradi,
• Stefano Cicchi,
• Sergio Moya,
• Giacomo Biagiotti and
• Barbara Richichi

Beilstein J. Org. Chem. 2020, 16, 2272–2281, doi:10.3762/bjoc.16.188

• observed. It is difficult to give a definitive answer, but the experiments demonstrated that the environment inside the dextran nanoparticles favored the solubilization of organic molecules like pyrene. This characteristic of the nanoparticles could bring applications in drug delivery since they are stable

Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides

• Mateo Berton,
• Kevin Sheehan,
• Andrea Adamo and
• D. Tyler McQuade

Beilstein J. Org. Chem. 2020, 16, 1343–1356, doi:10.3762/bjoc.16.115

• chloride coating, handling of LiCl (hygroscopic), LiCl equivalent optimization due to the solubilization over time. System setup: The same flow system was used as for the generation of Grignard reagents (Figure S2, Supporting Information File 1). The 10 × 100 mm (ID × length) column was half filled with

[3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin

• Margareta Sohora,
• Leo Mandić and
• Nikola Basarić

Beilstein J. Org. Chem. 2020, 16, 1296–1304, doi:10.3762/bjoc.16.110

• for solubilization of drugs or drug delivery [48], it would be interesting to investigate its effects to the photodecarboxylation reaction. Therefore, we investigated photochemical reactivity of phthalimide derivatives 1–3 (Figure 1) in solution without β-CD and in the β-CD inclusion complexes

The interaction between cucurbit[8]uril and baicalein and the effect on baicalein properties

• Xiaodong Zhang,
• Jun Xie,
• Zhiling Xu,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2020, 16, 71–77, doi:10.3762/bjoc.16.9

• stable and the decomposition curve equation was A = 0.4353 − 0.00004t. Therefore, the stability of the BALE–Q[8] inclusion complex in the same solvent was 7.5 times higher than that of BALE. Solubilization studies Solubilization studies were performed according to [41]. When compared with the unbound

• BALE solubility (Figure 8), the concentration in the presence of Q[8] reached at least 1.319 × 10−5 mol·L−1, which was a 6.98-fold increase for BALE over that in neutral water (1.889 × 10−6 mol·L−1), indicating that Q[8] had a significant solubilization effect on BALE. The solubility curve equation was

Reversible switching of arylazopyrazole within a metal–organic cage

• Anton I. Hanopolskyi,
• Soumen De,
• Michał J. Białek,
• Yael Diskin-Posner,
• Liat Avram,
• Moran Feller and
• Rafal Klajn

Beilstein J. Org. Chem. 2019, 15, 2398–2407, doi:10.3762/bjoc.15.232

• precipitation and re-solubilization of 1 (Figure S25, Supporting Information File 1). Overall, the reaction taking place in the system can be written down as (E-1)22 → (Z-1)2 + Z-1. Interestingly, however, despite the existence of Z-1 as two distinct species (encapsulated and non-encapsulated), the NMR spectrum

Aqueous olefin metathesis: recent developments and applications

• Valerio Sabatino and
• Thomas R. Ward

Beilstein J. Org. Chem. 2019, 15, 445–468, doi:10.3762/bjoc.15.39

• its structure, resulting in a non-ionic amphiphile (Figure 2). In water, PTS forms nanomicelles which contribute to the solubilization of water-insoluble substrates and catalysts, thus contributing significantly to improve olefin metathesis yields. The positive effect of this strategy was demonstrated

Phosphonic acid: preparation and applications

• Charlotte M. Sevrain,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

• with D2O as solvent that phosphonic acid appeared weakly soluble whereas the addition of K2CO3 induced its solubilization. Interestingly the increase of the number of phosphonic acid functional groups on a molecule is not systematically associated with an increase of its water solubility as exemplified

Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

• Joana M. Pais,
• Maria João Barroca,
• Maria Paula M. Marques,
• Filipe A. Almeida Paz and
• Susana S. Braga

Beilstein J. Org. Chem. 2017, 13, 2138–2145, doi:10.3762/bjoc.13.212

• , when the isolation of larger amounts of a solid complex is desired, by snap freezing and subsequent freeze-drying. In all methods, the solubilization of the guest, fisetin, was achieved using ethanol as the co-solvent, as a non-toxic and environmental friendly solvent. By this way, the inclusion

Chemical systems, chemical contiguity and the emergence of life

• Terrence P. Kee and
• Pierre-Alain Monnard

Beilstein J. Org. Chem. 2017, 13, 1551–1563, doi:10.3762/bjoc.13.155

• authors surmised that the product length (up 29 monomer units compared to 9 in aqueous set-ups) was possible due to solubilization of the products within the hydrophobic core of the vesicle bilayers. Recent investigations with potentially prebiotic fatty acid structures have confirmed these observations

• availability of the PAH molecules by providing a specific hydrophobic environment for their solubilization, thereby improving the energy conversion. A putative scenario for the evolution of chemical systems towards protocells. (A) Prebiotic chemistry in the geochemical environment delivers an inventory of

2-Methyl-2,4-pentanediol (MPD) boosts as detergent-substitute the performance of ß-barrel hybrid catalyst for phenylacetylene polymerization

• Julia Kinzel,
• Daniel F. Sauer,
• Marco Bocola,
• Marcus Arlt,
• Tayebeh Mirzaei Garakani,
• Andreas Thiel,
• Klaus Beckerle,
• Tino Polen,
• Jun Okuda and
• Ulrich Schwaneberg

Beilstein J. Org. Chem. 2017, 13, 1498–1506, doi:10.3762/bjoc.13.148

• membrane protein solubilization, but is leading to protein unfolding as a drawback. Disadvantageous of detergents is the tremendous reduction of selectivity due to denaturing the protein or the reduction of productivity by detergent micelles since hydrophobic compounds are most likely located inside the

G-Protein coupled receptors: answers from simulations

• Timothy Clark

Beilstein J. Org. Chem. 2017, 13, 1071–1078, doi:10.3762/bjoc.13.106

• , polar fragment such as the T4 lysozyme [10][11] or other suitable protein fragments [12]. Other techniques used to obtain GPCR crystals include mutations to enhance the thermal stability [13], solubilization with custom detergents [14] or in conjunction with high-affinity ligands, which promote one

Expression, purification and structural analysis of functional GABA transporter 1 using the baculovirus expression system

• Jing Hu,
• Chris Weise,
• Christoph Böttcher,
• Hua Fan and
• Jian Yin

Beilstein J. Org. Chem. 2017, 13, 874–882, doi:10.3762/bjoc.13.88

• 15 mM sodium phosphate buffer (pH 8.0). Prior to subsequent use of the affinity columns, 1 mL of PBS with 0.02% NaN3 was added to the sepharose, which was then stored at 4 °C. Cells were lysed in solubilization buffer (10 mM Tris, pH 7.8, 150 mM NaCl, 1 mM CaCl2, 2% DDM) containing 1 mM

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• activity in comparison with the parent CDs while the lipophilic ones (e.g., methylated CDs) demonstrate the strongest hemolytic activities [62]. As for parent CDs, these differences are ascribed to the different solubilization effects of lipid components and their sequestration in the external aqueous

• molecules into the lipid membrane leading to increase its fluidity. In contrast, at higher concentrations, the extraction of membrane constituents is ensured by micellar solubilization [84][85]. ii) Complexation of peptides and proteins and some applications Proteins are polymers of amino acids covalently

Nucleic acids through condensation of nucleosides and phosphorous acid in the presence of sulfur

• Tuomas Lönnberg

Beilstein J. Org. Chem. 2016, 12, 670–673, doi:10.3762/bjoc.12.67

• , solubilization by micelles [14][15] or a prebiotic oil slick [16] appears a more plausible scenario [17]. Results and Discussion Preparation of phosphorothioate oligonucleotides Equimolar amounts of thymidine and aq triethylammonium phosphite and a fourfold excess of S8 were suspended in toluene. The mixture was