Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction

• Thomas Brandt,
• Pascal Lentes,
• Jeremy Rudtke,
• Michael Hösgen,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2025, 21, 490–499, doi:10.3762/bjoc.21.36

• 19 and the diphenyl-substituted amine 20 show half-lives not significantly longer than the parent N-acetyl diazocine 1. Given the water solubility and the excellent switching behavior of parent 1 in aqueous media [3][13][20], the photochemical properties of water-soluble substituted N-acetyl

• -substituted N-acetyl diazocines 19–21 exhibit photostationary states (PSS) lower in their metastable configurations in analogy to amino-substituted azobenzenes and previously synthesized diazocines. We also investigated the switching properties of the water-soluble derivatives 13 and 21 in water at different

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

• Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

• , Ballester and co-workers reported on the preparation of an octapyridinium-based water-soluble superaryl-extended calix[4]pyrrole molecular container and used it as a capsule for desymmetrization reactions [41], where the reported compound acts both as sequestering and supramolecular protecting group. All of

Cyclodextrin-based rotaxanes for polymer materials: challenge on simultaneous realization of inexpensive production and defined structures

• Yosuke Akae

Beilstein J. Org. Chem. 2024, 20, 3026–3049, doi:10.3762/bjoc.20.252

• substitution/addition reactions became the standard for end-capping reactions, although a transition metal–catalyzed cross-coupling reaction has also been used to synthesize CD-based rotaxane. Typically, water-soluble components are prepared, after which the Suzuki coupling reaction in water is used to

• , most of their rotaxane structures required a complicated multistep synthesis as well as the introduction of polar substituents, such as carboxylic acid or sulfonic acid groups, to generate a water-soluble system, and these prevent the direct application of those frameworks to polymer systems. As the

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

• -physiological conditions further extend the parameter space in which CFPS can be performed. This extension would be highly desirable for a coupled CFPS and enzyme assay, where, e.g., an organic solvent is used to solubilize poorly water soluble substrates for the enzyme. In this study, we therefore aim to fill

• some of the gaps in the consideration of the general physical properties and potential effects on the performance of Escherichia coli-based CFPS. We use technical additives, such as water-soluble macromolecular polymers and salts, which are commonly used as deep eutectic solvents (DES) and extend the

• 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

Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA

• Ze-Nan Hu,
• Yan-Hui Wang,
• Jia-Bing Wu,
• Ze Chen,
• Dou Hong and
• Chi Zhang

Beilstein J. Org. Chem. 2024, 20, 1914–1921, doi:10.3762/bjoc.20.167

• zwitterionic water-soluble hypervalent iodine reagent (phenyliodonio)sulfamate (PISA). In water, PISA is strongly acidic, and the pH value can reach 2.05 in a saturated aqueous solution. With PISA, various indoles have been synthesized via C–H amination of 2-alkenylanilines involving an aryl migration

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

• acids). In order to expand DELs to the GBB reaction, compartmentation was proposed to confine an acidic catalyst into the lipophilic core of micelles, inaccessible to water soluble DNA. Micelles were made of a sulfonic acid substituted, amphiphilic copolymer 13. After reaction optimization, a narrow

Synthesis and properties of 6-alkynyl-5-aryluracils

• Ruben Manuel Figueira de Abreu,
• Till Brockmann,
• Alexander Villinger,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 898–911, doi:10.3762/bjoc.20.80

• additional ligand was used in the next attempts. Additionally, it was observed that by replacing the less polar solvent by a mixture of a more polar solvent and water in a 5:1 ratio, yields could be significantly improved. Therefore, sodium hydroxide was used as the water-soluble base, which also proved to

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

• Yue Ma Lorenzo Persi Yoko Yamakoshi Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland 10.3762/bjoc.20.71 Abstract With the aim of developing biocompatible and water-soluble C60 derivatives, three types of C60–peptide conjugates consisting

• successfully provide C60–peptide conjugates with one C60 and two peptide anchors as water-soluble moieties. Among three C60–peptide conjugates prepared, C60–oligo-Lys was soluble in water at neutral pH, and C60–oligo-Glu was soluble in buffer with a higher pH value, but C60–oligo-Arg was insoluble in water and

• most other solvents. C60–oligo-Lys and C60–oligo-Glu were characterized by 1H and 13C NMR. Photoinduced 1O2 generation was observed in the most soluble C60–oligo-Lys conjugate under visible light irradiation (527 nm) to show the potential of this highly water-soluble molecule in biological systems, for

Research progress on the pharmacological activity, biosynthetic pathways, and biosynthesis of crocins

• Zhongwei Hua,
• Nan Liu and
• Xiaohui Yan

Beilstein J. Org. Chem. 2024, 20, 741–752, doi:10.3762/bjoc.20.68

• Chinese Medicine, No. 10 Poyang Lake Road, Tuanbo New Town, Jinghai District, Tianjin 301617, China 10.3762/bjoc.20.68 Abstract Crocins are water-soluble apocarotenoids isolated from the flowers of crocus and gardenia. They exhibit various pharmacological effects, including neuroprotection, anti

New variochelins from soil-isolated Variovorax sp. H002

• Jabal Rahmat Haedar,
• Aya Yoshimura and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2024, 20, 692–700, doi:10.3762/bjoc.20.63

• transporters to form the siderophore Fe(III) complex extracellularly [2][3]. Subsequently, the stable and water soluble siderophore Fe(III) complex is transported across the cell membrane into the cytoplasm, where the iron is released from the complex by reduction, generating free Fe(II) ions that are

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

• chemistry; Introduction The terminology “molecular tweezers” was first introduced by Chen and Whitlock in 1978 through a seminal paper [1], wherein they presented a water-soluble molecular receptor composed of two caffeine recognition units linked by a semi-rigid diyne spacer. This ingenious design enabled

• attached functional arms. The formation of new hydrogen bonds between -OMe groups and protonated pyridine stabilizes a "W"-shaped open conformation. The conformation switch can be easily followed by NMR spectroscopy in solution. Remarkably, the water-soluble tweezers 1, when functionalized with hydrophobic

A new analog of dihydroxybenzoic acid from Saccharopolyspora sp. KR21-0001

• Rattiya Janthanom,
• Yuta Kikuchi,
• Hiroki Kanto,
• Tomoyasu Hirose,
• Arisu Tahara,
• Takahiro Ishii,
• Arinthip Thamchaipenet and
• Yuki Inahashi

Beilstein J. Org. Chem. 2024, 20, 497–503, doi:10.3762/bjoc.20.44

• [16]. KR21-0001A (1) is a new analog of 2,3-DHBA connected to N-acetylcysteine (Figure 2b). 1 has a stronger antioxidant activity than trolox, which is a water-soluble analog of the free radical scavenger α-tocopherol [17][18]. 1 shows no antimicrobial activity against bacteria and fungi. Conclusion

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

• Corporation [79], in which the inventors succeeded in the synthesis of water-soluble indigo derivatives and applied these compounds as solar energy storage systems using the aforementioned energy storage mechanism. However, detailed studies on kinetics and thermodynamics of the photoisomerization and thermal

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

• ][9][10][11]. The development of new amphiphiles with large polyaromatic panels for strong aromatic–aromatic interactions and nonionic side-chains on the other hand would grant access to water-soluble nanocarbons with tunable surface properties, which could expand noncovalent nanocarbon chemistry and

Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

• Ken-ichi Nakashima,
• Naohito Abe,
• Masayoshi Oyama,
• Hiroko Murata and
• Makoto Inoue

Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117

• the solution was evaporated in vacuo to afford a MeOH extract (47.2 g). The MeOH extract was partitioned three times with 1.6 L of ethyl acetate and water 1:1 (v/v), and the water-soluble fraction was further partitioned three times with 800 mL of n-butanol. The ethyl acetate and n-butanol solutions

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

• improves the chemical stability and aqueous solubility of the guest molecule and results in most of the cases in the formation of a water-soluble CD–guest complex [3]. Being recognized as non-toxic, biodegradable, and sustainable carriers, CDs have attracted wide interest as potential carriers in different

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

• Stéphanie Hesse

Beilstein J. Org. Chem. 2023, 19, 1537–1544, doi:10.3762/bjoc.19.110

• appearance of a solid–liquid biphasic mixture as the components of the DES are water-soluble. A large volume of water should be used since otherwise some DES traces are present in the NMR spectrum of the precipitate. Benzaldehydes having electron-donating or electron-withdrawing groups were studied as well

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

CO₂ complexation with cyclodextrins

• Cecilie Høgfeldt Jessen,
• Jesper Bendix,
• Theis Brock Nannestad,
• Heloisa Bordallo,
• Martin Jæger Pedersen,
• Christian Marcus Pedersen and
• Mikael Bols

Beilstein J. Org. Chem. 2023, 19, 1021–1027, doi:10.3762/bjoc.19.78

• were the following: β- (2) and γ-cyclodextrins (3) were also studied by Cramer, but gave no crystals although they might still bind CO2. Compound 4 (permethylated α-cyclodextrin) [16] is in terms of hydrogen bonding properties and polarity vastly different from 1 yet still water-soluble. Compounds 5

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

• Nan Yang,
• Yi-Yan Zhu,
• Wei-Xiu Lin,
• Yi-Long Lu and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

• supramolecular systems derived from water-soluble macrocycles, including cyclodextrins (CDs), calix[n]arenes (CXs), cucurbiturils (CBs), and pillararenes have been widely studied [2][6][7][8]. Similar to those macrocyclic acceptors, tribenzotriquinacene (TBTQ) derivatives, a class of versatile host molecules

• with a bowl-shaped C3v-symmetric skeleton, are capable of effectively encapsulating guest molecules [9][10][11][12][13][14][15]. In recently published studies [16][17], we have successfully synthesized two water-soluble hexacarboxylated tribenzotriquinacene derivatives, 2,2',2'',2''',2'''',2'''''-((12d

• improved water solubility of the supra-amphiphile due to the highly water-soluble behavior of TBTQ-C6 under alkaline conditions in its carboxyl anion form. As a result, the polymer chains were extended, releasing the entanglement and wrapping of the TPE fluorogens, thereby reducing the emission of the

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

• Austin Pounder,
• Eric Neufeld,
• Peter Myler and
• William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

• phenanthridinones produced, the authors were able to quickly afford novel fagaronine 117j and nitidine 117k derivatives. Rhodium-catalyzed reactions In 2002, the Lautens laboratory reported a tandem cyclization of arylboronate esters 118 with a variety of bicyclic alkenes 15 using a water-soluble Rh-catalytic

Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

• Nicoleta G. Hădărugă,
• Gabriela Popescu,
• Dina Gligor (Pane),
• Cristina L. Mitroi,
• Sorin M. Stanciu and
• Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

• biologically active molecules on CD-coated polymers used in chromatography [62]. PCA was used for the evaluation of the similarity/dissimilarity of some pesticides, especially fungicides and herbicides, using the effect of a water-soluble β-CD polymer on the apparent pesticide’s lipophilicity [63]. Also

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 and copper-corrole moieties upon photoexcitation. Moreover, the theoretical calculations suggested that the porphyrin moiety acted as a donor while the corrole unit acted as an acceptor in dimer 60. Recently S. Y. Yap and co-workers [38] used “click chemistry” to link a water-soluble porphyrin

• with a histidine like group for the development of theranostic agents. Firstly, zinc triazole-porphyrins 63 and 66a were synthesized by the click reaction between water-soluble azidoporphyrin 61 and ᴅ-propargylglycine 62 or trifunctional-propargyllysine 65 in 83.6% and 77% yield, respectively, under

• conjugates. In addition to this, the fluorescence studies suggested that the energy transfer was not efficient in Zn(II) porphyrin-BODIPY and 21,23-dithiaporphyrin-BODIPY conjugates. Dalip Kumar and his co-workers reported a CuAAC click reaction to prepare novel water soluble triazole-linked cationic

Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin

• János Máté Orosz,
• Dóra Ujj,
• Petr Kasal,
• Gábor Benkovics and
• Erika Bálint

Beilstein J. Org. Chem. 2023, 19, 294–302, doi:10.3762/bjoc.19.25

• complexation can lead to a significant solubility enhancement of poorly water-soluble molecules, and therefore it can enable the biological testing of drugs, which would otherwise not be possible by any other means [2][3]. Monosubstituted CDs contain only one hydroxy group modified with a functional group. In

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

• Solomiia Borova and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2023, 19, 217–230, doi:10.3762/bjoc.19.21

• clear bimodality, but the molar mass distribution was slightly lower (Ð = 1.45) compared to PBuOx obtained from EtOxMeOTf (Figure S14, Supporting Information File 1). POx-based block copolymers are well known to formulate poorly water soluble drugs and Haider et al. recently compared the drug loading