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

• ) resembles those of other amphiphilic marine siderophores such as marinobactins and aquachelins exhibiting the membrane affinity [21] as well as the self-assembling ability to form iron-containing vesicles [22]. This study presents another suite of amphiphilic peptidic siderophores originating in the

Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors

• Sedat Ünal,
• Gamze Varan,
• Juan M. Benito,
• Yeşim Aktaş and
• Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

• from the dosage system may be controlled by altering the physicochemical parameters (particle size, zeta potential, hydrophobicity) of the self-assembling units utilized to design nanoparticles [9][10][11][12]. However, oral nano drug delivery systems capable of providing all the necessary features

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

• Konstantin Lebedinskiy Volodymyr Lobaz Jindrich Jindrich Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Prague, Czech Republic Institute of Macromolecular Chemistry, Department of Supramolecular Systems and Self-Assembling Processes, Heyrovského nám. 2

First series of N-alkylamino peptoid homooligomers: solution phase synthesis and conformational investigation

• Maxime Pypec,
• Laurent Jouffret,
• Claude Taillefumier and
• Olivier Roy

Beilstein J. Org. Chem. 2022, 18, 845–854, doi:10.3762/bjoc.18.85

• ]. Conformational analysis and self-assembling properties The 1H NMR analysis of monomer 1 in various solvents including CDCl3, CD3CN, C6D6, CD3OD, D2O, and DMSO-d6 showed two sets of resonances in proportions varying from 75:25 to 90:10 (Table 3). These two sets of signals were characterized as the backbone cis

• proton exchange. Overall, the NMR study suggests that the N-methylamino glycine monomer and oligomers have a strong propensity to form intermolecular hydrogen bonds, an interesting and sought-after property for self-assembling and interaction with biological targets. Neat peptoids 1–6 were also

Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery

• Man-Ping Li,
• Nan Yang and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56

• (CXs), cyclodextrins (CDs), cucurbiturils (CBs), and pillararenes, are of particular interest because they can act as vehicles for anticancer drugs by either self-assembling into nanocarriers [14][15][16] or forming host–guest complexes with anticancer drugs [17][18][19][20]. Tribenzotriquinacene (TBTQ

A resorcin[4]arene hexameric capsule as a supramolecular catalyst in elimination and isomerization reactions

• Tommaso Lorenzetto,
• Fabrizio Fabris and
• Alessandro Scarso

Beilstein J. Org. Chem. 2022, 18, 337–349, doi:10.3762/bjoc.18.38

• structures endowed with catalytic features are full covalent units (e.g., cyclodextrins, cucurbiturils, pillararenes and other derivatives) whose synthesis can be sometimes time consuming. Alternatively, supramolecular catalysts can be obtained through self-assembling units [18][19], metal-ligand components

Synthesis and bioactivity of pyrrole-conjugated phosphopeptides

• Qiuxin Zhang,
• Weiyi Tan and
• Bing Xu

Beilstein J. Org. Chem. 2022, 18, 159–166, doi:10.3762/bjoc.18.17

• -terminal of the peptide, a self-assembling motif (ᴅ-phenylalanine-ᴅ-phenylalanine (ff)) [69] as the main backbone, and an enzymatic trigger ᴅ-phosphotyrosine (py). This design presents a substrate of alkaline phosphatase (ALP) for EISA. Based on this structure, a considerable number of studies have

• . According to this rationale, replacing the Nap capping group in 1 with a dipyrrole or a tripyrrole segment at the N-terminal generates 2a and 2b. Introducing two or three glycine residues between the pyrrole segment and the self-assembling segment produces 2c–h, which would help to understand the role of a

• the sidechain of NBD-ffky or NBD-ffkpy [66], another previously studied self-assembling peptide, produces 13 and 14. In addition, 15a–c consist of only pyrrole and glycine units, which should help delineate the roles of the self-assembling motif and the enzymatic triggers. Synthesis The synthesis of

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

Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings

• Ivan P. Mosiagin,
• Olesya A. Tomashenko,
• Dar’ya V. Spiridonova,
• Mikhail S. Novikov,
• Sergey P. Tunik and
• Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2021, 17, 1490–1498, doi:10.3762/bjoc.17.105

• skeletons that are inaccessible via Pd-catalyzed cyclization. Keywords: arylation; pyridine; pyrrole; radical cyclization; tris(trimethylsilyl)silane; Introduction Polycyclic heteroaromatic molecules, which have a tunable electronic structure and excellent self-assembling properties, are highly desirable

Enzyme-instructed morphological transition of the supramolecular assemblies of branched peptides

• Dongsik Yang,
• Hongjian He and
• Bing Xu

Beilstein J. Org. Chem. 2020, 16, 2709–2718, doi:10.3762/bjoc.16.221

• role in endocytic pathways. Figure 1A shows the molecular design of the branched peptides, which also act as hydrogelator precursors [44][45]. The branch consists of (i) a hydrophilic ʟ-peptide segment for enzymatic recognition and cleavage, (ii) a self-assembling ᴅ-peptide sequence composed of a 2

pH- and concentration-dependent supramolecular self-assembly of a naturally occurring octapeptide

• Goutam Ghosh and
• Gustavo Fernández

Beilstein J. Org. Chem. 2020, 16, 2017–2025, doi:10.3762/bjoc.16.168

• implications for the development of a wide range of functional materials [2][3][4][5][6][7][8]. Peptides are arguably the most eminent candidates among all types of biological self-assembling building blocks because of a number of key properties. This includes a high biocompatibility [9][10][11][12][13][14

• , as mentioned above. The pH-responsive self-assembling behavior of peptides has a great importance in drug delivery, and since PEP-1 contains rich cationic residues, such as Arg, this system can be an interesting potential candidate for DDS and as an antibacterial agent [71]. Biocompatibility, drug

Efficient synthesis of 3,6,13,16-tetrasubstituted-tetrabenzo[a,d,j,m]coronenes by selective C–H/C–O arylations of anthraquinone derivatives

• Seiya Terai,
• Yuki Sato,
• Takuya Kochi and
• Fumitoshi Kakiuchi

Beilstein J. Org. Chem. 2020, 16, 544–550, doi:10.3762/bjoc.16.51

• tetrabenzo[a,d,j,m]coronene product indicated its self-assembling behavior in CDCl3. Keywords: C–H arylation; C–O arylation; oxidative cyclization; polycyclic aromatic hydrocarbons; ruthenium catalyst; Introduction Polycyclic aromatic hydrocarbons (PAHs) and their derivatives have attracted much attention

• ,m]coronenes having two different types of substituents. Coronene derivatives such as hexabenzocoronenes and ovalenes have been extensively studied because of their optoelectronic and self-assembling properties [34][35][36][37][38][39][40][41][42][43][44]. Various synthetic methods have been

• , and the π–π* transitions (p-band) for 7aa, 7bb, and 7ba were observed at 426 nm [11]. The peaks corresponding to n–π* transitions (α-band) were observed at 456–469 nm and were red-shifted with growing intensity as the number of hexyloxy groups increases. The self-assembling property of tetrabenzo[a,d

Influence of the cis/trans configuration on the supramolecular aggregation of aryltriazoles

• Sara Tejera,
• Giada Caniglia,
• Rosa L. Dorta,
• Andrea Favero,
• Javier González-Platas and
• Jesús T. Vázquez

Beilstein J. Org. Chem. 2019, 15, 2881–2888, doi:10.3762/bjoc.15.282

• "click" chemistry [16][17][18] of azides and alkynes catalyzed by Cu(I) salts, the CuAAC reaction. Self-assembling properties were not observed for any of the prepared monotriazoles, namely the 4-substituted 1-glucopyranosyltriazoles 1a–g and 2a–g (Scheme 1) [15]. However, most ditriazoles 7a–g and 8a–g

Host–guest interactions between p-sulfonatocalix[4]arene and p-sulfonatothiacalix[4]arene and group IA, IIA and f-block metal cations: a DFT/SMD study

• Valya K. Nikolova,
• Cristina V. Kirkova,
• Silvia E. Angelova and
• Todor M. Dudev

Beilstein J. Org. Chem. 2019, 15, 1321–1330, doi:10.3762/bjoc.15.131

• ligands with novel features. They have found various applications in chemical [5], analytical [6][7][8][9], and engineering materials fields (self-assembling monolayers, surfactants, sensors [10][11]), in polymer synthesis [12][13], controlled drug-delivery systems [14], and so on, besides the biochemical

Fabrication of supramolecular cyclodextrin–fullerene nonwovens by electrospinning

• Hiroaki Yoshida,
• Ken Kikuta and
• Toshiyuki Kida

Beilstein J. Org. Chem. 2019, 15, 89–95, doi:10.3762/bjoc.15.10

• gemini surfactants [7], diphenylalanine [8], cyclodextrin (CD)/CD derivatives [9][10][11][12], heteroditopic monomers [13], and self-assembling oligopeptides [14] have been successfully electrospun to produce continuous fibers. Among these molecules, CD is a unique compound that can form fibers despite

Design, synthesis and structure of novel G-2 melamine-based dendrimers incorporating 4-(n-octyloxy)aniline as a peripheral unit

• Cristina Morar,
• Pedro Lameiras,
• Attila Bende,
• Gabriel Katona,
• Emese Gál and
• Mircea Darabantu

Beilstein J. Org. Chem. 2018, 14, 1704–1722, doi:10.3762/bjoc.14.145

• macromolecular shape in solution). DFT calculations (in solution), (VT) NMR and IR (KBr) spectroscopy supported these assignments. TEM analysis revealed the ability of the title compounds towards self-assembling into homogeneously packed spherical nano-aggregates. Conclusions: The (non)covalent synthesis and

Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies

• Artur Jabłoński,
• Yannic Fritz,
• Hans-Achim Wagenknecht,
• Rafał Czerwieniec,
• Tytus Bernaś,
• Damian Trzybiński,
• Krzysztof Woźniak and
• Konrad Kowalski

Beilstein J. Org. Chem. 2017, 13, 2521–2534, doi:10.3762/bjoc.13.249

• solution. In respect to the complementary oligothymidine T10 template in water, compounds 3 and 5 both show a self-assembling behavior according to canonical base–base pairing. However, in buffer solution, derivative 5 was much more effective than 3 in binding to the T10 template. Furthermore the adenine

• % to the double-stranded template is significantly higher compared to the single-stranded templates and must be assigned either to a triple-helix-like binding or intercalation, or a mixture of both (Table 3). In summary, compounds 3 and 5 show a self-assembling behavior in the presence of the

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

• light scattering (DLS) The supramolecular properties of all regioisomers of NA-γ-CD (2-O-, 3-O-, 6-O-) were investigated by DLS. We analyzed the dependence of self-assembling of the isomers on external stimuli such as agitation and temperature. The 3-O-isomer 2b shows co-existence of two types of

β-Cyclodextrin- and adamantyl-substituted poly(acrylate) self-assembling aqueous networks designed for controlled complexation and release of small molecules

• Liang Yan,
• Duc-Truc Pham,
• Philip Clements,
• Stephen F. Lincoln,
• Jie Wang,
• Xuhong Guo and
• Christopher J. Easton

Beilstein J. Org. Chem. 2017, 13, 1879–1892, doi:10.3762/bjoc.13.183

• Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia 10.3762/bjoc.13.183 Abstract Three aqueous self-assembling poly(acrylate) networks have been designed to gain insight into the factors controlling the complexation and release of small molecules within them. These

• self-assembling aqueous polymer networks through the complexation of hydrophobic polymer substituents by cyclodextrin oligomers [1][2][3][4] and cyclodextrin substituted polymers [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] to form cross-links between polymer strands is well-established

• designed into the structure of aqueous networks formed between a β-cyclodextrin-substituted poly(acrylate) and three adamantyl-substituted poly(acrylate)s. Accordingly, we report an ITC, 1H NMR and UV–vis spectroscopic and rheological study of three self-assembling networks formed between the 8.8% 6A-(2

Grip on complexity in chemical reaction networks

• Albert S. Y. Wong and
• Wilhelm T. S. Huck

Beilstein J. Org. Chem. 2017, 13, 1486–1497, doi:10.3762/bjoc.13.147

• dissipative self-assembling structures, creating new forms of smart materials [31][32][33][34][35]. Yet, we are severely limited by too few examples of systems which are both extensive enough to exhibit dynamics, and at the same time, simple enough to be tunable [36]. In this perspective, we will attempt to

• chemical dissipative networks from organic structures. This has resulted in numerous exciting examples, ranging from functional out-of-equilibrium systems that can perform logic operations to dissipative self-assembling structures, creating new forms of smart materials (Figure 3a–d) [31][32][33][34][35][74

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

• minimal number and the specific nature of these prebiotic components/processes (i.e., that ‘irreducible core’ required for functional emergence) remains an open empirical question [46]. One needs to try different combinations of precursors, taking part in various reactive and self-assembling processes

• 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

• will defend the view that in order to reconstruct this process a strict ‘bottom-up’ approach should be pursued, starting with chemical precursors of biomolecules, rather than with fully functional biomolecules. Whereas the encapsulation of biopolymers (DNA, RNA, proteins) or cell extracts in self

Interactions between shape-persistent macromolecules as probed by AFM

• Johanna Blass,
• Jessica Brunke,
• Franziska Emmerich,
• Cédric Przybylski,
• Vasil M. Garamus,
• Artem Feoktystov,
• Roland Bennewitz,
• Gerhard Wenz and
• Marcel Albrecht

Beilstein J. Org. Chem. 2017, 13, 938–951, doi:10.3762/bjoc.13.95

• used in low equilibrium concentrations. Since AFM even allows the investigation of single molecules, such as DNA [37][38] or molecular self-assembling based on “Dip-Pen” nanolithography [39], it was chosen as the most reliable technique to probe highly cooperative recognition processes. The

Sulfamide chemistry applied to the functionalization of self-assembled monolayers on gold surfaces

• Loïc Pantaine,
• Vincent Humblot,
• Vincent Coeffard and
• Anne Vallée

Beilstein J. Org. Chem. 2017, 13, 648–658, doi:10.3762/bjoc.13.64

• applications in medicinal chemistry, sulfamide groups have been incorporated in self-assembling molecules [22][23][24][25][26][27], peptides [28], polymers [29], ligands [30], chiral auxiliaries [31][32][33] and in organocatalysts [34][35][36][37]. In light of the importance of the sulfamide functionality, our

Inhibition of peptide aggregation by means of enzymatic phosphorylation

• Kristin Folmert,
• Malgorzata Broncel,
• Hans v. Berlepsch,
• Christopher H. Ullrich,
• Mary-Ann Siegert and
• Beate Koksch

Beilstein J. Org. Chem. 2016, 12, 2462–2470, doi:10.3762/bjoc.12.240

• components on the peptide conformation during this process. This knowledge could become a useful tool in employing enzymatic phosphorylation and dephosphorylation as triggers for or inhibitors of amyloid formation, as it was previously shown for a self-assembling, supramolecular hydrogel [44]. Results

DNA functionalization by dynamic chemistry

• Zeynep Kanlidere,
• Oleg Jochim,
• Marta Cal and
• Ulf Diederichsen

Beilstein J. Org. Chem. 2016, 12, 2136–2144, doi:10.3762/bjoc.12.203

• analogue. Keywords: base-pairing; base-pair mismatch; DNA functionalization; DNA templates; dynamic combinatorial chemistry; D-threoninol based scaffolds; Introduction The well-defined duplex structure, self-assembling by base-pair recognition, and the accessibility by solid-phase synthesis make DNA