A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE

• Tue Heesgaard Jepsen,
• Emil Glibstrup,
• François Crestey,
• Anders A. Jensen and
• Jesper Langgaard Kristensen

Beilstein J. Org. Chem. 2017, 13, 988–994, doi:10.3762/bjoc.13.98

• [6,6]-bicyclic lactone 26. Pharmacological evaluation The binding properties of two synthesized CD fragments (compounds 9 and 26) were characterized in a [3H]-epibatidine binding assay using membranes from HEK293 cells stably expressing the rat heteromeric nAChR subtypes α4β2, α4β4 and α3β4 as

Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands

• Nikolay V. Lukashev,
• Gennadii A. Grabovyi,
• Dmitry A. Erzunov,
• Alexey V. Kazantsev,
• Gennadij V. Latyshev,
• Alexei D. Averin and
• Irina P. Beletskaya.

Beilstein J. Org. Chem. 2017, 13, 564–570, doi:10.3762/bjoc.13.55

• arylaminocholanes and cholane-diaminoanthraquinone derivatives by Pd- and Cu-catalyzed amination. Such compounds not only have cation binding properties, but also might be easily introduced in lipid membranes to form ion channels. Appropriate close location of lipophilic steroid fragments in bis(cholanediamino

Spectral and DFT studies of anion bound organic receptors: Time dependent studies and logic gate applications

• Srikala Pangannaya,
• Neethu Padinchare Purayil,
• Shweta Dabhi,
• Venu Mankad,
• Prafulla K. Jha,
• Satyam Shinde and
• Darshak R. Trivedi

Beilstein J. Org. Chem. 2017, 13, 222–238, doi:10.3762/bjoc.13.25

• response of the anion detection process. The anion binding properties of receptors R1 and R2 (4.5 × 10−5 M in DMSO), have been studied through the addition of 2 equiv of a series of anions as their tetrabutylammonium salts (F−, Cl−, Br−, I−, NO3−, HSO4−, H2PO4− and AcO− at concentrations of 1 × 10−2 M in

Phosphated cyclodextrins as water-soluble chiral NMR solvating agents for cationic compounds

• Cira Mollings Puentes and
• Thomas J. Wenzel

Beilstein J. Org. Chem. 2017, 13, 43–53, doi:10.3762/bjoc.13.6

• derivatization can be used to alter the solubility, binding properties of substrates, and ultimately enantioselectivity properties of the CDs. The cavity of CDs has the secondary hydroxy groups at one opening and the primary ones at the other and the opening to the cavity at the secondary side is larger than

New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation

• Pavel Nagorny and
• Zhankui Sun

Beilstein J. Org. Chem. 2016, 12, 2834–2848, doi:10.3762/bjoc.12.283

• of the catalyst was found to directly correlate with the stability of supramolecular complex, and L21 capable of forming multiple halogen bonds at the same time was found to be the most active catalyst. The binding properties of L19–L21 toward halides in the solid state, in solution, and in the

Computational methods in drug discovery

• Sumudu P. Leelananda and
• Steffen Lindert

Beilstein J. Org. Chem. 2016, 12, 2694–2718, doi:10.3762/bjoc.12.267

A modular approach to neutral P,N-ligands: synthesis and coordination chemistry

• Vladislav Vasilenko,
• Torsten Roth,
• Clemens K. Blasius,
• Sebastian N. Intorp,
• Hubert Wadepohl and
• Lutz H. Gade

Beilstein J. Org. Chem. 2016, 12, 846–853, doi:10.3762/bjoc.12.83

• demanding 2,6-di(isopropyl)phenyl group as the N-aryl substituent induced only slight structural changes (complexes of ligand 2a vs 2b), mostly in the orientation of the phenyl rings of the phosphorus donor and the position of the cyclooctadiene co-ligand. To further explore the binding properties of the P

Size-controlled and redox-responsive supramolecular nanoparticles

• Raquel Mejia-Ariza,
• Gavin A. Kronig and
• Jurriaan Huskens

Beilstein J. Org. Chem. 2015, 11, 2388–2399, doi:10.3762/bjoc.11.260

• ) grafted with β-cyclodextrin (CD) and a positively charged ferrocene (Fc)-terminated poly(amidoamine) dendrimer, with a monovalent stabilizer at the surface. Fc was chosen for its loss of CD-binding properties when oxidizing it to the ferrocenium cation. The ionic strength was shown to play an important

Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity

• Louis P. Sandjo,
• Victor Kuete and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2015, 11, 1667–1699, doi:10.3762/bjoc.11.183

• be suggested as being partly responsible for the activity. Furthermore, cytotoxic modes of action of pyridoacridine alkaloids include DNA-binding properties, topoisomerase (TOPO) inhibition [91] or the production of reactive oxygen species (ROS) [92][93]. It was shown that planar iminoquinone

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

• called a hetero-heteraphane (11, Figure 2). A number of cyclophane derivatives have been employed as hosts, and their guest-binding properties have been widely investigated. A variety of reviews related to the cyclophane chemistry has been published. Although monomeric cyclophanes show moderate guest

Azobenzene-based inhibitors of human carbonic anhydrase II

• Leander Simon Runtsch,
• David Michael Barber,
• Peter Mayer,
• Michael Groll,
• Dirk Trauner and
• Johannes Broichhagen

Beilstein J. Org. Chem. 2015, 11, 1129–1135, doi:10.3762/bjoc.11.127

• 1c offers the second-lowest affinity (Ki = 55.4 nM), which seems counter-intuitive, as the only difference with respect to 1b is the connection of the ethyl chains by an oxygen atom to a morpholine ring. This does not only affect the binding properties, but also the π–π* band, which is 46 nm blue

• carboxylate 1i) show higher affinities at around 30 µM. The latter also shows a distribution from UV to blue maximal absorbance. We therefore speculate that electronics do not have a primary effect on the binding properties towards hCAII, but rather the sole presence of an aryl sulfonamide is sufficient. It

Glycoluril–tetrathiafulvalene molecular clips: on the influence of electronic and spatial properties for binding neutral accepting guests

• Yoann Cotelle,
• Marie Hardouin-Lerouge,
• Stéphanie Legoupy,
• Olivier Alévêque,
• Eric Levillain and
• Piétrick Hudhomme

Beilstein J. Org. Chem. 2015, 11, 1023–1036, doi:10.3762/bjoc.11.115

• appeared in a head-to-tail arrangement and short TTF···TTF intermolecular distances (3.51 Å) were determined between two clips in the solid state. Binding properties In order to establish the influence of electronic and spatial properties of the clips towards binding ability of neutral electrodeficient

• guest molecules, we have chosen compounds 3 and 4 for this study. Molecular clip 3 presents better π-donating ability according to CV study and a smaller interplanar TTF distance (7.41 Å compared to calculated 9.2 Å for clip 4). Binding properties were studied using 1,3-dinitrobenzene (m-DNB) as a weak

• through an induced-fit mechanism with a recognition process on the basis of the size rather than the acceptor strength. We can suppose that the presence of stronger π-donor TTF sidewalls in clip 3 favorize donor–acceptor interactions and consequently the binding properties towards m-DNB. We have also

Peptide–polymer ligands for a tandem WW-domain, an adaptive multivalent protein–protein interaction: lessons on the thermodynamic fitness of flexible ligands

• Katharina Koschek,
• Vedat Durmaz,
• Oxana Krylova,
• Marek Wieczorek,
• Shilpi Gupta,
• Martin Richter,
• Alexander Bujotzek,
• Christina Fischer,
• Rainer Haag,
• Christian Freund,
• Marcus Weber and
• Jörg Rademann

Beilstein J. Org. Chem. 2015, 11, 837–847, doi:10.3762/bjoc.11.93

• correlates with the experimentally observed binding properties of the multivalent ligands. The construction and experimental investigation of further peptide–polymer conjugates will show, whether the results reported here will be helpful for the construction of even more potent multivalent and/or

Impact of multivalent charge presentation on peptide–nanoparticle aggregation

• Daniel Schöne,
• Boris Schade,
• Christoph Böttcher and
• Beate Koksch

Beilstein J. Org. Chem. 2015, 11, 792–803, doi:10.3762/bjoc.11.89

• switching [15] applications, a variety of specific and site selective binding properties are available [16]. In particular, the specificity of Watson–Crick base pairing of DNA nucleotides can be used for the directed and predictable self-assembly of nanoparticles [17]. The DNA mediated assembly of

Orthogonal dual-modification of proteins for the engineering of multivalent protein scaffolds

• Michaela Mühlberg,
• Michael G. Hoesl,
• Christian Kuehne,
• Jens Dernedde,
• Nediljko Budisa and
• Christian P. R. Hackenberger

Beilstein J. Org. Chem. 2015, 11, 784–791, doi:10.3762/bjoc.11.88

• protein with two unnatural functional groups. For the functionalization of these unnatural moieties, we combined CuAAC with oxime ligation for the attachment of two different ligands, galactose and biotin, to the thermostable lipase TTL. The double functionalized TTL scaffold exhibited lectin binding

• properties while conserving its natural enzymatic activity, thereby demonstrating the principle applicability of this double protein functionalization strategy to the generation of new multivalent binding scaffolds. Currently, we are further expanding our general dual-labeling strategy to other protein

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

• Franziska Klitsche,
• Julian Ramcke,
• Julia Migenda,
• Andreas Hensel,
• Tobias Vossmeyer,
• Horst Weller,
• Silvia Gross and
• Wolfgang Maison

Beilstein J. Org. Chem. 2015, 11, 678–686, doi:10.3762/bjoc.11.77

• chemistry after immobilization. Immobilization on ZnO NPs Three different catecholates were selected to study the binding properties to ZnO NPs (Figure 2). Monomeric PEG-catecholate 14 [46] and the tripodal homologue 3 were chosen to study the stability of the coatings and the particles in aqueous solution

Formation of nanoparticles by cooperative inclusion between (S)-camptothecin-modified dextrans and β-cyclodextrin polymers

• Thorbjørn Terndrup Nielsen,
• Catherine Amiel,
• Laurent Duroux,
• Kim Lambertsen Larsen,
• Lars Wagner Städe,
• Reinhard Wimmer and
• Véronique Wintgens

Beilstein J. Org. Chem. 2015, 11, 147–154, doi:10.3762/bjoc.11.14

• prepared with a degree of substitution of (S)-camptothecin between 3.1 and 10.2%. The binding properties with β-cyclodextrin and β-cyclodextrin polymers were measured by isothermal titration calorimetry and fluorescence spectroscopy, showing no binding with β-cyclodextrin but high binding with β

• ). Binding properties and formation of nanoparticles The ability to form inclusion complexes with β-CD and β-CD-polymers was determined by isothermal titration calorimetry (ITC) and fluorescence spectroscopy. The β-CD polymer (D70HPβ-CD) had been prepared from a 70 kDa dextran backbone modified with 6

• prepared with a DS of (S)-camptothecin between 3.1 and 10.2%. It was measured by ITC and fluorescence spectroscopy that the binding properties with β-CD polymers depended significantly on the molecular weight of the dextran backbone of the (S)-camptothecin-dextran polymers, where the strongest binding was

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

• Lidija-Marija Tumir,
• Marijana Radić Stojković and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

• toward particular nucleobase recognition, with very few referent compounds for any final conclusion about the binding properties of phenanthridine moiety alone. Nevertheless, binding data obtained for ethidium bromide and 8-amino-substituted derivatives with methylated or protonated heterocyclic N5

Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction

• Vicky Gheerardijn,
• Jos Van den Begin and
• Annemieke Madder

Beilstein J. Org. Chem. 2014, 10, 2566–2572, doi:10.3762/bjoc.10.268

• increased attention for incorporation in modified nucleic acid structures both for the design of aptamers with enhanced binding properties as well as the construction of catalytic DNA and RNA. As a shortcut alternative to the incorporation of multiple modified residues, each bearing one extra functional

Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives

• Marijana Radić Stojković,
• Marko Škugor,
• Łukasz Dudek,
• Jarosław Grolik,
• Julita Eilmes and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2175–2185, doi:10.3762/bjoc.10.225

• different interactions with DNA/RNA. Future prospects also include the synthesis of fluorescent DBTAA derivatives, which are expected to transfer observed intriguing DBTAA-DNA/RNA binding properties in a lower concentration range and broaden the set of DBTAA applications by cell-bioimaging. Such

Organophosphorus chemistry

• Paul R. Hanson

Beilstein J. Org. Chem. 2014, 10, 2087–2088, doi:10.3762/bjoc.10.217

• number of important fields. Among the more prominent features that elevate their status as a unique and versatile class of compounds, include variable oxidation states, multivalency, asymmetry and metal-binding properties. Their presence in bioactive natural products, endogenous biomolecules, small

Macrocyclic bis(ureas) as ligands for anion complexation

• Claudia Kretschmer,
• Gertrud Dittmann and
• Johannes Beck

Beilstein J. Org. Chem. 2014, 10, 1834–1839, doi:10.3762/bjoc.10.193

• (urea) ring. The ammonium ions are located in the saddle shaped cavity formed by the twisted bis(urea). The binding properties of 1 and 2 towards anions were studied by 1H NMR spectroscopy. As 2 was sufficiently soluble, tetrahydrofuran (THF) turned out as a suitable solvent for the spectroscopic

Photoswitchable precision glycooligomers and their lectin binding

• Daniela Ponader,
• Sinaida Igde,
• Marko Wehle,
• Katharina Märker,
• Mark Santer,
• David Bléger and
• Laura Hartmann

Beilstein J. Org. Chem. 2014, 10, 1603–1612, doi:10.3762/bjoc.10.166

• functionalities along the backbone, polymer scaffolds make it particularly difficult to correlate their chemical structure with the resulting binding properties. Recently, we introduced a novel synthetic approach towards monodisperse, sequence-defined glycooligomers, so-called precision glycomacromolecules, via

Synthesis and solvodynamic diameter measurements of closely related mannodendrimers for the study of multivalent carbohydrate–protein interactions

• Yoann M. Chabre,
• Alex Papadopoulos,
• Alexandre A. Arnold and
• René Roy

Beilstein J. Org. Chem. 2014, 10, 1524–1535, doi:10.3762/bjoc.10.157

• quantitative structure–activity relationships (QSARs). In most of the studies related to aglycon modifications, it was concluded that aromatic glycosides possessed improved binding properties due to the ubiquitous presence of aromatic amino acids in the cognate binding sites [23][24][25]. This is also

Direct and indirect single electron transfer (SET)-photochemical approaches for the preparation of novel phthalimide and naphthalimide-based lariat-type crown ethers

• Dae Won Cho,
• Patrick S. Mariano and
• Ung Chan Yoon

Beilstein J. Org. Chem. 2014, 10, 514–527, doi:10.3762/bjoc.10.47

• these compounds are crown ethers, whose preparation, and metal and ammonium cation-binding properties were explored thoroughly by Petersen and Lehn [68][69]. Early pioneering efforts by Gokel and coworkers [70][71][72][73] in this area have shown that novel, lariat-type crown ethers display unique

• binding properties with a variety of cationic guests. In typical cases, carbon or nitrogen-pivot lariat crown ethers are comprised of crown ether cores and one or more heteroatom-containing side arms that are covalently bonded to carbon or nitrogen in the core. The skeletal framework and position of

• lariat-type crown ethers that could have potentially interesting metal cation binding properties. As can be seen by inspection of the synthetic sequence shown in Scheme 14, the preparation of lariat-type crown ethers 72–74 by employing this strategy began with the synthesis of the α-silyl ether