Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides

• Kartik Temburnikar and
• Katherine L. Seley-Radtke

Beilstein J. Org. Chem. 2018, 14, 772–785, doi:10.3762/bjoc.14.65

• stability, ii) altered hydrogen bonding motifs, and iii) altered molecular recognition properties [25][29][37][58]. Because of these changes, C-nucleosides have been useful in the study of RNA and DNA processing enzymes, as well as drug design efforts and novel supramolecular structures [12][29][59

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of γ-cyclodextrin

• Markéta Bláhová,
• Sergey K. Filippov,
• Lubomír Kováčik,
• Jiří Horský,
• Simona Hybelbauerová,
• Zdenka Syrová,
• Tomáš Křížek and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2017, 13, 2509–2520, doi:10.3762/bjoc.13.248

• CDs are attractive building blocks for various types of supramolecular structures [6][7]. Necessary non-covalent interactions depend on the type and derivatization of CD, on lipophilicity, shape, and size of the guest molecule, and on conditions such as temperature, pH, or solvent used [8]. In

• as a ditopic monomer of the AB type with groups A and B undergoing an association of 1:1. However, a number of alternate or competing interactions may occur, as mentioned above, γ-CD is known to form also inclusion complexes of 2:1 stoichiometry and formation of cyclic supramolecular structures my

• and γ-CD/γ-CD. In Figure 10 various putative interactions of NA-γ-CD are schematically depicted indicating how small supramolecular structures such as supramolecular oligomers or micelles as well as large one such as aggregates can originate. As all three NA-γ-CD regioisomers were prepared, the effect

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

• Martina Tireli,
• Silvija Maračić,
• Stipe Lukin,
• Marina Juribašić Kulcsár,
• Dijana Žilić,
• Mario Cetina,
• Ivan Halasz,
• Silvana Raić-Malić and
• Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

• notation as R22(18) [54]. Although the same motif formed by the analogous hydrogen bond is observed in other three structures (Table S3, Supporting Information File 1), the final supramolecular structures of 5–8 differ, from one-dimensional chains to three-dimensional network. It should be mentioned that

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

• activator of Vγ9Vδ2 T cells [53][54] (Figure 3D). Phosphonic acid is a function that is readily involved in hydrogen bonds thus generating auto-assembling supramolecular structures [55] or, when a second organic partner possessing basic groups is present (e.g., amine), mixt supramolecular materials [56][57

Framing major prebiotic transitions as stages of protocell development: three challenges for origins-of-life research

• Ben Shirt-Ediss,
• Sara Murillo-Sánchez and
• Kepa Ruiz-Mirazo

Beilstein J. Org. Chem. 2017, 13, 1388–1395, doi:10.3762/bjoc.13.135

• in which an alternative reaction domain is offered (especially for hydrophobic species to interact, or for water-producing reactions to proceed). In recent years, evidence is accumulating to support various potential functions that these self-assembling supramolecular structures could have as reactor

How and why kinetics, thermodynamics, and chemistry induce the logic of biological evolution

• Addy Pross and
• Robert Pascal

Beilstein J. Org. Chem. 2017, 13, 665–674, doi:10.3762/bjoc.13.66

• in support of that view. Results and Discussion From thermodynamic self-assembly to kinetic self-assembly Organised supramolecular structures are commonly formed when favourable interactions lead to the assembly of different components [18]. The release of chemical binding energy, i.e., the

Radical polymerization by a supramolecular catalyst: cyclodextrin with a RAFT reagent

• Kohei Koyanagi,
• Yoshinori Takashima,
• Takashi Nakamura,
• Hiroyasu Yamaguchi and
• Akira Harada

Beilstein J. Org. Chem. 2016, 12, 2495–2502, doi:10.3762/bjoc.12.244

• catalyst; Introduction The folding of proteins in biological systems, the replication of DNA, and specific substrate recognition by enzymes play important roles in forming supramolecular structures, achieving functions, and maintaining life [1][2][3][4][5][6]. The crystal structures of RNA polymerase, DNA

Amidofluorene-appended lower rim 1,3-diconjugate of calix[4]arene: synthesis, characterization and highly selective sensor for Cu²⁺

• Rahman Hosseinzadeh,
• Mohammad Nemati,
• Reza Zadmard and
• Maryam Mohadjerani

Beilstein J. Org. Chem. 2016, 12, 1749–1757, doi:10.3762/bjoc.12.163

• supramolecular structures, especially calixarene derivatives, has been an appealing field for research [14]. Calixarene has been considered as an effective molecular scaffold in the improvement of fluorescent and chromogenic sensors, especially for metal-ion recognition [14][15]. Calix[4]arene derivatives having

Superstructures with cyclodextrins: chemistry and applications III

• Gerhard Wenz and
• Eric Monflier

Beilstein J. Org. Chem. 2016, 12, 937–938, doi:10.3762/bjoc.12.91

• ; Cyclodextrins (CDs) are of increasing scientific and commercial interest because they are readily available, harmless and well-defined, forming sophisticated supramolecular structures in aqueous media. More than 2,300 publications and more than 1,200 patents appeared in 2015 in which CDs played a significant

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

• Vito Rizzi,
• Sergio Matera,
• Paola Semeraro,
• Paola Fini and
• Pinalysa Cosma

Beilstein J. Org. Chem. 2016, 12, 549–563, doi:10.3762/bjoc.12.54

• presence of CDs to prevent its degradation under irradiation. UV–vis, FTIR–ATR and CV measurements suggested the formation of supramolecular structures involving the employed CDs and mainly the pyrimidine ring of S4TdR. 1H NMR analyses confirmed such indication, unveiling the presence of inclusion

• powerful tools to clearly establish the presence of supramolecular structures involving S4TdR and CDs. Furthermore, assuming the formation of a 1:1 host–guest complex, in order to give details about the inclusion complexes the binding constant (K) and the stoichiometry of interaction, the Benesi–Hildebrand

• interaction between S4TdR and CDs. After the assessment of the presence of these supramolecular structures involving CDs and S4TdR and in addition to the stoichiometry of the interaction, detailed information was obtained using FTIR–ATR and NMR analysis. FTIR–ATR measurements FTIR–ATR measurements were

Art, auto-mechanics, and supramolecular chemistry. A merging of hobbies and career

• Eric V. Anslyn

Beilstein J. Org. Chem. 2016, 12, 362–376, doi:10.3762/bjoc.12.40

• Abstract Art? Maybe one can, but the similarly is striking (Figure 1). Besides having an aspect of beauty, supramolecular structures are created to achieve a chemical function or task. These functions range from imparting mechanical changes [11][12][13], to altering material properties [14][15], to

• functional models, it is not surprising that my career has focused on the creation of new molecular and supramolecular structures designed to execute a particular function or achieve a certain task. Further, while we all know “beauty is in the eye of the beholder”, many of our group’s chemical structures are

My maize and blue brick road to physical organic chemistry in materials

• Anne J. McNeil

Beilstein J. Org. Chem. 2016, 12, 229–238, doi:10.3762/bjoc.12.24

• providing a portable and potentially inexpensive method for sensing. Considering how naïve my understanding of gelation was at the time, I am still surprised that my proposal idea worked almost exactly as described. Molecular gels form through the self-assembly of small molecules into supramolecular

• structures, such as ribbons, fibers, and sheets. This self-aggregation is driven by noncovalent interactions, including hydrogen bonding, π stacking, van der Waals interactions, and halogen bonding. Physical interactions amongst these larger structures lead to gel formation. Because noncovalent interactions

A journey in bioinspired supramolecular chemistry: from molecular tweezers to small molecules that target myotonic dystrophy

• Steven C. Zimmerman

Beilstein J. Org. Chem. 2016, 12, 125–138, doi:10.3762/bjoc.12.14

• is the development of complex supramolecular systems. So much of supramolecular chemistry is inspired by biology, it is only natural that the complexity of biological systems be modeled in supramolecular systems. Thus, future developments will lead to multicomponent supramolecular structures/systems

Supramolecular structures based on regioisomers of cinnamyl-α-cyclodextrins – new media for capillary separation techniques

• Gabor Benkovics,
• Ondrej Hodek,
• Martina Havlikova,
• Zuzana Bosakova,
• Pavel Coufal,
• Milo Malanga,
• Eva Fenyvesi,
• Andras Darcsi,
• Szabolcs Beni and
• Jindrich Jindrich

Beilstein J. Org. Chem. 2016, 12, 97–109, doi:10.3762/bjoc.12.11

• This work focuses on the preparation and application of supramolecular structures based on mono-cinnamyl-α-cyclodextrins (Cin-α-CD). Pure regioisomers of Cin-α-CD having the cinnamyl moiety at the 2-O- or at the 3-O-position, respectively, were prepared, characterized and applied in capillary

• electrophoresis as additives to the background electrolyte. These new monomer units with a potential to self-organize into supramolecular structures were synthesized via a straightforward one-step synthetic procedure and purified using preparative reversed-phase chromatography allowing a large scale separation of

• the regioisomers. The ability of the monomers to self-assemble was proved by various methods including NMR spectroscopy and dynamic light scattering (DLS). The light scattering experiments showed that the monomer units have distinguishable ability to form supramolecular structures in different

Supramolecular polymer assembly in aqueous solution arising from cyclodextrin host–guest complexation

• Jie Wang,
• Zhiqiang Qiu,
• Yiming Wang,
• Li Li,
• Xuhong Guo,
• Duc-Truc Pham,
• Stephen F. Lincoln and
• Robert K. Prud’homme

Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7

• blocks in supramolecular structures and functional materials. These are exemplified by catenanes [20][21], rotaxanes [21][22][23][24][25], polyrotaxanes [24][25][26][27][28][29], polymers and polymer networks [12][22][26][30][31][32][33][34]. The focus of this review is on recent developments in the

Aggregation behaviour of amphiphilic cyclodextrins: the nucleation stage by atomistic molecular dynamics simulations

• Giuseppina Raffaini,
• Antonino Mazzaglia and
• Fabio Ganazzoli

Beilstein J. Org. Chem. 2015, 11, 2459–2473, doi:10.3762/bjoc.11.267

• correlating their structures with the pharmaceutical properties. Keywords: aggregation; amphiphilic cyclodextrins; micelles; molecular dynamics simulations; nanoparticles; self-assembly; Introduction Inclusion complexes with supramolecular structures formed by native or modified cyclodextrins (CDs) are

• -dependence of the supramolecular structures, or the pH dependence of water solubility, so as to improve our understanding of their activity as drug delivery systems [19][20] and of the biological fate of the assemblies [21][22]. The balance between the hydrophobic and the polar groups on the two CD rims

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

• Masahiko Iyoda and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

• produce supramolecular structures, and their TTF units stack face-to-face to form columnar structures using the fastener effect. Based on redox-active self-organizing supramolecular structures, conducting nanoobjects are constructed by doping of TTF oligomers with oxidants after the formation of such

• accelerate self-aggregation of molecules in solution [6][7][8] and then produce the functional one-dimensional (1D) or two-dimensional (2D) supramolecular structures, which are very important in advanced nanosciences [9][10][11]. For the formation of the nanostructured objects such as fibers, rods, tubes

Donor–acceptor type co-crystals of arylthio-substituted tetrathiafulvalenes and fullerenes

• Xiaofeng Lu,
• Jibin Sun,
• Shangxi Zhang,
• Longfei Ma,
• Lei Liu,
• Hui Qi,
• Yongliang Shao and
• Xiangfeng Shao

Beilstein J. Org. Chem. 2015, 11, 1043–1051, doi:10.3762/bjoc.11.117

• between TTFs and fullerenes are key factors that give rise to the effective surface contact for the stabilization of the resulting supramolecular structures. Because pristine TTF cannot form good enough surface contact with fullerenes due to the shape and size mismatch [42], chemical modifications of TTF

• factors to stabilize the resulting supramolecular structures. Meanwhile, the solid state absorption study indicates that the inclusion complexes display a photoexcited electronic transition between Ar–S–TTF and C60/C70. To gain further insight into the structural features of Ar-S-TTF upon complexation

• ratio of the co-crystals, this work further demonstrates that Ar-S-TTFs are promising candidates to serve as receptors for fullerenes and have diverse supramolecular structures. Crystal structures The single crystalline structure of the complex is suitable for X-ray single crystal diffraction

Potential of acylated peptides to target the influenza A virus

• Daniel Lauster,
• Damian Pawolski,
• Julian Storm,
• Kai Ludwig,
• Rudolf Volkmer,
• Henry Memczak,
• Andreas Herrmann and
• Sumati Bhatia

Beilstein J. Org. Chem. 2015, 11, 589–595, doi:10.3762/bjoc.11.65

• supramolecular structures [20][21]. Stearylated peptides, closely related to C18-s2s, C18-rs2s and C18-PeBGF assemble as supramolecular structures with a critical micelle concentration (CMC) between 0.8–0.9 µM and a size between 0.2 and 2.3 µm depending on the peptide concentration [12]. The rather large size

• supramolecular structures with hydrodynamic diameters of 184.3 nm and 573.1 nm as per volume distribution profile (Figure 1). We observed much bigger aggregates in the case of C18-rs2s with a hydrodynamic diameter of 818.8 nm (PDI = 0.328). The volume size distribution was multimodal for C18-s2s showing higher

• -order aggregates of different sizes at 20 µM concentration (see Supporting Information File 1). To address if the tendency of C18-PeBGF to form larger supramolecular structures becomes prominent at higher concentrations, we analyzed C18-PeBGF in DLS measurements at a concentration of 100 µM, too. Indeed

Superstructures with cyclodextrins: Chemistry and applications II

• Gerhard Wenz

Beilstein J. Org. Chem. 2015, 11, 271–272, doi:10.3762/bjoc.11.30

• soluble in water and able to solubilize hydrophobic active ingredients, they are broadly used in biomedical applications [4]. CDs are also well known to complex suitable monomeric and polymeric guest molecules, leading to supramolecular structures and topological compounds, such as rotaxanes and

Synthesis and characterization of pH responsive D-glucosamine based molecular gelators

• Navneet Goyal,
• Hari P. R. Mangunuru,
• Bargav Parikh,
• Sonu Shrestha and
• Guijun Wang

Beilstein J. Org. Chem. 2014, 10, 3111–3121, doi:10.3762/bjoc.10.328

• ; naproxen; organogelator; pH responsive; self-assembly; Introduction Low molecular weight gelators (LMWGs) have drawn great attention over the past few decades due to the formation of supramolecular structures and their potential applications as advanced materials [1][2][3][4][5][6][7]. LMWGs are also

Host–guest-driven color change in water: influence of cyclodextrin on the structure of a copper complex of poly((4-hydroxy-3-(pyridin-3-yldiazenyl)phenethyl)methacrylamide-co-dimethylacrylamide)

• Nils Retzmann,
• Gero Maatz and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 2480–2483, doi:10.3762/bjoc.10.259

• and led to an increased usage of dyes in the field of optical recording media [8][9]. However, up to now, only little is known about the interactions of azo–metal chelate complexes in supramolecular structures with CD as a modulator for macromolecular effects. Few reports dealt with the reversibility

• -copper complexes in aqueous media. In result we could show that supramolecular structures and metal complexes open up a wide field for the development of novel stimuli-responsive polymer materials. We thus described that the simple addition of copper and γ-CD to a poly((4-hydroxy-3-(pyridin-3-yldiazenyl

Molecular ordering at electrified interfaces: Template and potential effects

• Thanh Hai Phan and
• Klaus Wandelt

Beilstein J. Org. Chem. 2014, 10, 2243–2254, doi:10.3762/bjoc.10.233

• molecular self-organization on surfaces and to simulate the working principles of the derived molecular devices. This so-called “bottom-up” strategy, i.e., the formation of supramolecular structures from vapor deposited simpler building blocks has become an important research direction in ultra-high vacuum

Pyrene-modified PNAs: Stacking interactions and selective excimer emission in PNA₂DNA triplexes

• Alex Manicardi,
• Lucia Guidi,
• Alice Ghidini and
• Roberto Corradini

Beilstein J. Org. Chem. 2014, 10, 1495–1503, doi:10.3762/bjoc.10.154

• ][15][16][17][18][19][20]. Furthermore, pyrene has been shown to favour self-assembly processes of supramolecular structures [21][22][23][24][25][26][27][28] and interact with carbon nanostructures such as nanotubes [29] or graphene [30], thus allowing to create composite material with special

Carbohydrate PEGylation, an approach to improve pharmacological potency

• M. Eugenia Giorgi,
• Rosalía Agusti and
• Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2014, 10, 1433–1444, doi:10.3762/bjoc.10.147

• PEGylation. Hydrogels with supramolecular structures have been obtained by inclusion complexation of the PEG grafted dextrans with α-cyclodextrins. The unique thermoreversible sol-transition properties of the gels were considered interesting for drug delivery applications [65]. Conclusion The advantage of