Improved deconvolution of natural products’ protein targets using diagnostic ions from chemical proteomics linkers

• Andreas Wiest and
• Pavel Kielkowski

Beilstein J. Org. Chem. 2024, 20, 2323–2341, doi:10.3762/bjoc.20.199

• large tag, which significantly changes the molecular weight of the given protein. The shift on the gel can be then visualized by protein-specific antibody or coomassie staining. The linkers applied to perform the gel shift assay contain a linear PEG polymer with an approximate size ranging from one to

Cell-free protein synthesis with technical additives – expanding the parameter space of in vitro gene expression

• Tabea Bartsch,
• Stephan Lütz and
• Katrin Rosenthal

Beilstein J. Org. Chem. 2024, 20, 2242–2253, doi:10.3762/bjoc.20.192

• macromolecules. PEG, a water-soluble macromolecular polymer, is a commonly used crowding agent to mimic the cellular environment in vitro [25]. Interestingly, it has been observed that different proteins have different PEG-8000 concentration optima [27]. The standard composition of the in-house CFPS system

• the impact of the polymer itself is greater than that of the increased viscosity. A positive effect on the stability and activity of the model enzyme β-ᴅ-glucuronidase by the addition of carboxymethylcellulose has already been reported [49]. However, the effects and states of molecular crowding in the

• cell are much more complex than what can be mimicked by the sole addition of a polymer. The diffusion of macromolecules depends on the perceived viscosity in the cell, which is inhomogeneous and depends on the location in the cell and its growth phase [50][51]. Comparing the salt concentrations, the

Metal-free double azide addition to strained alkynes of an octadehydrodibenzo[12]annulene derivative with electron-withdrawing substituents

• Naoki Takeda,
• Shuichi Akasaka,
• Susumu Kawauchi and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2024, 20, 2234–2241, doi:10.3762/bjoc.20.191

• , the double azide addition reaction was applied to polymer crosslinking and the mechanical properties of the self-standing polymer films were compared. Results and Discussion Strain-promoted azide–alkyne cycloaddition Octadehydrodibenzo[12]annulene (DBA) with electron-withdrawing carbonyl substituents

• -standing film became insoluble due to the occurrence of strain-promoted double azide–alkyne cycloaddition (Figure 6a). The mechanical properties of the polymer films were then examined to observe the impact of crosslinking. A PVC-N3 film was prepared by a solvent-cast method on a Teflon boat. The strain

• metal-free click reaction was employed to crosslink a partially azidated poly(vinyl chloride). The crosslinking proceeded by simply mixing the polymer and crosslinker in THF and evaporating, and the formation of the crosslinked polymer film was confirmed by the strain–stress curves. The developed method

Factors influencing the performance of organocatalysts immobilised on solid supports: A review

• Zsuzsanna Fehér,
• Dóra Richter,
• Gyula Dargó and
• József Kupai

Beilstein J. Org. Chem. 2024, 20, 2129–2142, doi:10.3762/bjoc.20.183

• performance is crucial to the development of high performance immobilised organocatalysts. Review Characteristics of the solid support Considering the support type, organic polymer-supported, silica-supported [20][21][22][23][24][25], glass beads [26] and magnetic nanoparticle-supported [27][28][29][30][31

• ][32] organocatalysts are pivotal in the field of immobilised organocatalysts. Polymer-supported organocatalysts are commonly immobilised on polystyrene (PS) [28][33][34][35][36][37][38], as well as on other materials such as nylon 6,6 [15], chitosan [39][40], and polymethylhydrosiloxane (PMHS) [41

• ]. The role of the polymers as supports for catalysts is not merely passive. These supports significantly influence the reaction environment and catalytic efficiency [42]. Attachment methods, spacer lengths, and polymer nature profoundly impact the catalyst's performance and recyclability. Various

Cage-like microstructures via sequential Ugi reactions in aqueous emulsions

• Rita S. Alqubelat,
• Yaroslava A. Menzorova and
• Maxim A. Mironov

Beilstein J. Org. Chem. 2024, 20, 2078–2083, doi:10.3762/bjoc.20.179

• Colloidosomes are microcapsules built on the basis of colloidal particles [1]. In the past 20 years, many methods have been proposed for the synthesis based on different particle types (inorganic, polymer, and composite) [2][3][4] and shape [5] (spheres, discs, and fibers). A distinctive feature of

• usually more complex than conventional colloidosomes and involves several stages. Pickering emulsions or polymer spheres coated with a monolayer of colloidal particles are used as initial templates for synthesis [11]. Thus, cage-like structures have been obtained using phase inversion in Pickering

• the formation of a double Pickering emulsion using a microfluidic technique. Solidification of this structure and removal of the template resulted in the formation of nonspherical capsules with large openings [13]. The use of a polymer matrix that can swell in an organic solvent made it possible to

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

• Ignaz Betcke,
• Alissa C. Götzinger,
• Maryna M. Kornet and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

• as [MCM-41-2N-Pd(OAc)2] [130] and Pd-SH-silica bound catalysts [131] have also been successfully employed in this three-component pyrazole synthesis. Interestingly, the latter catalyst system does not require a copper cocatalyst. Tang's research group further extended polymer synthesis by using the

• consecutive three-component approach in a polymer analogous fashion with diynes 105, terephthaloyl chloride (106), and hydrazines to synthesize high molecular weight pyrazole-based polymers 107 (Scheme 38) [132]. The materials 107 fluoresce in THF solutions, form thin films, and possess high thermal stability

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

• Cristina Martini,
• Muhammad Idham Darussalam Mardjan and
• Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

Polymer degrading marine Microbulbifer bacteria: an un(der)utilized source of chemical and biocatalytic novelty

• Weimao Zhong and
• Vinayak Agarwal

Beilstein J. Org. Chem. 2024, 20, 1635–1651, doi:10.3762/bjoc.20.146

• novelty. In this review, we summarize the distribution of Microbulbifer bacteria, activities of the various polymer degrading enzymes that these bacteria produce, and an up-to-date summary of the natural products that have been isolated from Microbulbifer strains. We argue that these bacteria have been

• from Microbulbifer Agarases Agarose is a natural polymer consisting of a linear chain of alternating residues of 3-O-linked β-ᴅ-galactopyranose and 4-O-linked 3,6-anhydro-α-ʟ-galactose. Agarose is a major component of agar, a polysaccharide present in the cell walls of some red algae [101]. Agarases

• agarases to be encoded which belonged to the GH-50 agarase family. The enzymes were named AgaA50, AgaB50, and AgaC50. Biochemical characterization of these three enzymes revealed that AgaA50 and AgaC50 generated neoagarobiose products implying cleavage within the agarose polymer (endolytic hydrolysis). The

New triazinephosphonate dopants for Nafion proton exchange membranes (PEM)

• Fátima C. Teixeira,
• António P. S. Teixeira and
• C. M. Rangel

Beilstein J. Org. Chem. 2024, 20, 1623–1634, doi:10.3762/bjoc.20.145

• incorporation of other compounds into these polymeric materials to participate in the proton conduction or to surpass the water or electrolyte dependency [15][21]. The most studied and commercially available proton exchange membranes consist of Nafion, a hydrophobic perfluorosulfonated polymer with sulfonic

• incorporation of the chosen dopants into a Nafion polymer using a casting method (Figure 4). It was expected that the dopants could act as proton carriers, improving the proton conduction of the membranes. The new membranes had a 1 wt % loading of TPs since our previous [27] results showed that 1 wt % is

Electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines under mild conditions with a proton-exchange membrane reactor

• Koichi Mitsudo,
• Atsushi Osaki,
• Haruka Inoue,
• Eisuke Sato,
• Naoki Shida,
• Mahito Atobe and
• Seiji Suga

Beilstein J. Org. Chem. 2024, 20, 1560–1571, doi:10.3762/bjoc.20.139

• hydrogen [13][14][15][16][17][18]. Meanwhile, electrochemical systems using solid polymer electrolytes (SPEs) have recently attracted significant attention [19]. Among these, proton-exchange membrane (PEM) reactors are powerful tools for hydrogenation [20][21][22][23][24][25][26][27][28][29][30][31][32][33

Synthesis of substituted triazole–pyrazole hybrids using triazenylpyrazole precursors

• Simone Gräßle,
• Laura Holzhauer,
• Nicolai Wippert,
• Olaf Fuhr,
• Martin Nieger,
• Nicole Jung and
• Stefan Bräse

Beilstein J. Org. Chem. 2024, 20, 1396–1404, doi:10.3762/bjoc.20.121

• predominant product (see 18i and 18j). In total, 13 groups could be attached to the different triazenylpyrazoles, yielding 18 products (see Table 1). In analogy to reported procedures for cleavage of polymer-bound triazenes [23], we attempted to develop the first protocol for synthesizing pyrazolyl azides 19

Diameter-selective extraction of single-walled carbon nanotubes by interlocking with Cu-tethered square nanobrackets

• Guoqing Cheng and
• Naoki Komatsu

Beilstein J. Org. Chem. 2024, 20, 1298–1307, doi:10.3762/bjoc.20.113

• depend on their structures [1]. To obtain specific structures, remarkable progress has been made in separation of SWNTs by various methods such as gel column chromatography [2][3], aqueous two-phase extraction (ATPE) [4][5], and polymer wrapping [6][7]. As compared with these methods, our separation by

Synthesis of indano[60]fullerene thioketone and its application in organic solar cells

• Yong-Chang Zhai,
• Shimon Oiwa,
• Shinobu Aoyagi,
• Shohei Ohno,
• Tsubasa Mikie,
• Jun-Zhuo Wang,
• Hirofumi Amada,
• Koki Yamanaka,
• Kazuhira Miwa,
• Naoyuki Imai,
• Takeshi Igarashi,
• Itaru Osaka and
• Yutaka Matsuo

Beilstein J. Org. Chem. 2024, 20, 1270–1277, doi:10.3762/bjoc.20.109

• crystalline polymer donor PNTz4T [32] was used. Compared with t-Bu-FIDS, t-Bu-FIDO achieved 3.71% PCE with larger JSC and higher VOC. With PNTz4T, t-Bu-FIDS exhibited low performance, with JSC of only 4 mA/cm2. This lower VOC may be attributable to a suboptimal BHJ structure between PNTz4T and t-Bu-FIDS

Competing electrophilic substitution and oxidative polymerization of arylamines with selenium dioxide

• Vishnu Selladurai and
• Selvakumar Karuthapandi

Beilstein J. Org. Chem. 2024, 20, 1221–1235, doi:10.3762/bjoc.20.105

• polymer 1. The polymer was isolated from the reaction after 3 h, and the supernatant was analyzed for other soluble products. The UV–vis spectrum of polymer 1 dispersed in methanol showed two major peaks at ≈271 and ≈561 nm (Figure S1, Supporting Information File 1), corresponding to the π→π* and

• due to N–H stretching of the polymer [43][44]. The peak appearing at around 3000 cm−1 corresponded to the aryl C–H stretching. The peaks observed at 1593 and 1479 cm−1 were associated with C=C and C=N stretching, respectively. The obtained result was further supported by solid-state synthesis of

• relative to NH2. Scheme 3 shows the reaction of o-anisidine with SeO2. Similar to aniline, a large quantity of o-anisidine was transformed into polymer, labelled polymer 2. The UV–vis and FTIR spectra of polymer 2 are shown in Figures S1 and S2, Supporting Information File 1, respectively. The spectral

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

• Mohd Farhan Ansari,
• Atul Kumar Maurya,
• Abhishek Kumar and
• Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

Light on the sustainable preparation of aryl-cored dibromides

• Fabrizio Roncaglia,
• Alberto Ughetti,
• Nicola Porcelli,
• Biagio Anderlini,
• Andrea Severini and
• Luca Rigamonti

Beilstein J. Org. Chem. 2024, 20, 1076–1087, doi:10.3762/bjoc.20.95

• significant importance as reactive building blocks in polymer and materials chemistry. Their preparation primarily relies on established synthetic methods using molecular bromine or N-bromosuccinimide, known for their reliability and effectiveness. However, from a sustainability perspective, these methods

• building blocks for polymer and materials chemists, offering improved sustainability compared to standard methodologies. Experimental General Solvents and reagents were commercial grade and used as received. 1H NMR spectra were acquired with a Bruker Avance 400 spectrometer (Billerica, MA, USA). The

Synthesis and characterization of water-soluble C₆₀–peptide conjugates

• Yue Ma,
• Lorenzo Persi and
• Yoko Yamakoshi

Beilstein J. Org. Chem. 2024, 20, 777–786, doi:10.3762/bjoc.20.71

• and nonionic polymer, poly(vinylpyrrolidone) (PVP) [25] and applied these to several in vitro biological assays to report DNA photocleavage [26] and related ROS generation [27][28], antimicrobial photoactivity [29], chondrogenesis-promoting activity [30][31], photocytotoxicity [32][33], and GST enzyme

• -soluble C60 and C70 derivatives by covalently attaching biocompatible water-soluble polymers, such as polyethylene glycol (PEG) [37][38] and PVP [39]. Although these C60– and C70–polymer conjugates revealed high water-solubility, it was found that they, especially the PEG conjugates, formed micelle-like

Switchable molecular tweezers: design and applications

• Pablo Msellem,
• Maksym Dekthiarenko,
• Nihal Hadj Seyd and
• Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

• to the employment of GO–CuBr without overshadowing its applications [113]. Shirini et al. utilized the polymer poly(4-vinylpyridine) (P4VPy) for the immobilization of nanoparticles in lieu of silica, due to the strong affinity of the pyridyl group towards metals and its ability to undergo hydrogen

• . immobilized carbon nanotubes on sulfonated polyacrylamide creating polymer/carbon nanotube composites, which could also be employed in the synthesis of BIMs [115][116]. This methodology used a catalyst loading of 5 mol % under reflux conditions (85 °C) in acetonitrile for 30–40 minutes with product yields

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• synthesized thiepine-containing polymers designed to undergo redox-driven bent-to-planar conformational changes [63]. However, upon electrochemical oxidation of the drop-cast film of polymer 13, the authors observed the conversion of the dithienobenzothiepine monomeric units into dithienonaphthalenes, which

Photochromic derivatives of indigo: historical overview of development, challenges and applications

• Gökhan Kaplan,
• Zeynel Seferoğlu and
• Daria V. Berdnikova

Beilstein J. Org. Chem. 2024, 20, 228–242, doi:10.3762/bjoc.20.23

• in the presence of water in organic solvent. In 2023, Huang, Hecht, Priimagi and co-workers provided the first study of the photoswitching of Ν,Ν'-derivatized indigos in polymer films of different rigidity and described the molecular design strategy allowing to improve the photoswitching performance

• within the polymer matrix [67]. Based on the obtained results, the authors are aiming to translate the photoswitching effect to the macroscopic level and to achieve the modulation of macroscopic properties of materials by red light. Conclusion From the first report on the photochromic N,N'-diacetylindigo

Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

• Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

• . This endeavor aims to delineate new directions for prospective applications of push–pull chromophores. Notably, in polymer chemistry, significant progress has been made in employing [2 + 2] CA–RE reactions for polymers as a valuable post-functionalization treatment [9][10]. However, this topic lies

Long oligodeoxynucleotides: chemical synthesis, isolation via catching-by-polymerization, verification via sequencing, and gene expression demonstration

• Yipeng Yin,
• Reed Arneson,
• Alexander Apostle,
• Adikari M. D. N. Eriyagama,
• Komal Chillar,
• Emma Burke,
• Martina Jahfetson,
• Yinan Yuan and
• Shiyue Fang

Beilstein J. Org. Chem. 2023, 19, 1957–1965, doi:10.3762/bjoc.19.146

• monomers N,N-dimethylacrylamide and sodium acrylate, and the cross-linking agent N,N'-methylenebisacrylamide were added, and the polymerization was initiated with ammonium persulfate and N,N,N',N'-tetramethylethylenediamine (TMEDA). The full-length sequence 3 was co-polymerized into the polymer 5, and

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• Karolis Leitonas Brigita Vigante Dmytro Volyniuk Audrius Bucinskas Pavels Dimitrijevs Sindija Lapcinska Pavel Arsenyan Juozas Vidas Grazulevicius Department of Polymer Chemistry and Technology, Kaunas University of Technology, Radvilenu pl. 19, LT-50254, Kaunas, Lithuania Latvian Institute of

GlAIcomics: a deep neural network classifier for spectroscopy-augmented mass spectrometric glycans data

• Thomas Barillot,
• Baptiste Schindler,
• Baptiste Moge,
• Elisa Fadda,
• Franck Lépine and
• Isabelle Compagnon

Beilstein J. Org. Chem. 2023, 19, 1825–1831, doi:10.3762/bjoc.19.134

• biopolymer have been established decades ago and are commonly used in a routine and automated manner. However, the development of such technology for the sequencing of the third class of biological polymer – glycans, also known as carbohydrates, saccharides, or "sugars" – lags far behind. This lack of

• (position and anomericity). Based on this basic principle, the identification of an unknown carbohydrate proceeds as follows: the polymer is fragmented in monomers, yet maintaining information on the initial structure and the spectroscopic fingerprint (frequency and intensity of the vibrational modes) of