Elucidation of a masked repeating structure of the O-specific polysaccharide of the halotolerant soil bacteria Azospirillum halopraeferens Au4

• Elena N. Sigida,
• Yuliya P. Fedonenko,
• Alexander S. Shashkov,
• Nikolay P. Arbatsky,
• Evelina L. Zdorovenko,
• Svetlana A. Konnova,
• Vladimir V. Ignatov and
• Yuriy A. Knirel

Beilstein J. Org. Chem. 2016, 12, 636–642, doi:10.3762/bjoc.12.62

• deleterious salt stress effects by producing osmoprotectants and enzymes and inducing plant systemic resistance. Additionally, they enhance plant growth by the synthesis of phytohormones and vitamins, fixation of atmospheric nitrogen, and solubilization of soil phosphates [2][3][4]. Strains of the species

Enabling technologies and green processes in cyclodextrin chemistry

• Giancarlo Cravotto,
• Marina Caporaso,
• Laszlo Jicsinszky and
• Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

• -conventional techniques, the largest number of papers is dealing with US-assisted CD solubilization or re-dissolution and in a minor extends CD derivatization. Analogously, ball milling is mostly used in the preparation of CD complexes rather than synthetic preparations. MW-assisted CD chemistry covers 1/4–1/5

• various diseases [102][103]. Although these reactors exhibit an excellent energy and mass efficacy, their use in CD derivatization is just a curiosity. However, exhausting the complexation ability of various CD derivatives is advantageous in solubilization and stereoselective reactions. Delattre and

Physical properties and biological activities of hesperetin and naringenin in complex with methylated β-cyclodextrin

• Waratchada Sangpheak,
• Jintawee Kicuntod,
• Roswitha Schuster,
• Thanyada Rungrotmongkol,
• Peter Wolschann,
• Nawee Kungwan,
• Helmut Viernstein,
• Monika Mueller and
• Piamsook Pongsawasdi

Beilstein J. Org. Chem. 2015, 11, 2763–2773, doi:10.3762/bjoc.11.297

• a much better solubilization effect on naringenin than β-CD [31]. The solubility of the naringenin/CD complex was increased to approximately 1.34, 1.60 and 1.52 mg/mL by complexing with β-CD, DM-β-CD and TM-β-CD (trimethyl-β-CD), respectively, while the solubility of free naringenin was 4.38 μg/mL

• behavior, as the greatest solubilization occurs within 30 minutes as well. These results were in good agreement with a previous report [42] in which the dissolution of hesperetin and naringenin complexed with β-CD was studied. The improved dissolution rate observed may be due to the increase in solubility

Co-solvation effect on the binding mode of the α-mangostin/β-cyclodextrin inclusion complex

• Chompoonut Rungnim,
• Sarunya Phunpee,
• Manaschai Kunaseth,
• Supawadee Namuangruk,
• Kanin Rungsardthong,
• Thanyada Rungrotmongkol and
• Uracha Ruktanonchai

Beilstein J. Org. Chem. 2015, 11, 2306–2317, doi:10.3762/bjoc.11.251

• -solvent enhances the solubility of α-MGS with some effects on the binding affinity with β-CD, depending on the concentration employed. Keywords: α-mangostin; β-cyclodextrin; binary complex; inclusion complex; Introduction Solubilization of otherwise poorly soluble drugs under physiological conditions to

• -solvent molecules in the six simulation systems. Estimation of solubilization parameters. The apparent binary complexation constant, Kbapp, as a function of ethanol concentration. Percentage of hydrogen bond (% H-bond) formed between the hydroxy groups of α-MGS and the β-CD molecules, O6–H6(α-MGS)···O6(β

Hexacoordinate Ru-based olefin metathesis catalysts with pH-responsive N-heterocyclic carbene (NHC) and N-donor ligands for ROMP reactions in non-aqueous, aqueous and emulsion conditions

• Shawna L. Balof,
• K. Owen Nix,
• Matthew S. Olliff,
• Sarah E. Roessler,
• Arpita Saha,
• Kevin B. Müller,
• Ulrich Behrens,
• Edward J. Valente and
• Hans-Jörg Schanz

Beilstein J. Org. Chem. 2015, 11, 1960–1972, doi:10.3762/bjoc.11.212

• ][51][52][53] and/or solubilization [31][32] in aqueous media. One of the most intriguing applications of water-soluble metathesis catalysts is the production of latexes via ring-opening metathesis polymerization (ROMP) in emulsion. However, to date very few reports have successfully employed well

Properties of cationic monosubstituted tetraalkylammonium cyclodextrin derivatives – their stability, complexation ability in solution or when deposited on solid anionic surface

• Martin Popr,
• Sergey K. Filippov,
• Nikolai Matushkin,
• Juraj Dian and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2015, 11, 192–199, doi:10.3762/bjoc.11.20

• environment for encapsulation of a wide range of organic and inorganic molecules [2]. Therefore CDs and their derivatives are most often utilized in pharmaceutical industry for drug solubilization [3] and delivery [4]. Recently, we have published an article on the synthesis of a complete series of cationic

Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols

• Bianca Rossi,
• Nadia Pastori,
• Simona Prosperini and
• Carlo Punta

Beilstein J. Org. Chem. 2015, 11, 66–73, doi:10.3762/bjoc.11.10

• acetone have limited applications as solvents, both due to economic issues and with regards to their limited solubilization properties. For this reason, we verified the possibility of using dichloromethane as a solvent by decreasing the amount of acetone down to 1 mL (Table 1, entry 4), and to 5 mmol

Effects of RAMEA-complexed polyunsaturated fatty acids on the response of human dendritic cells to inflammatory signals

• Éva Rajnavölgyi,
• Renáta Laczik,
• Viktor Kun,
• Lajos Szente and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3152–3160, doi:10.3762/bjoc.10.332

• mediated through the GP120 receptor without interfering with the cell membrane structure. Keywords: cell membrane; cell surface markers; cyclodextrin; enzyme immunoassay; flow cytometry; monocyte-derived dendritic cells; proinflammatory cytokines; RAMEA; solubilization; Introduction The n−3

• ethanol, because they could not be dissolved in water owing to their long alkyl chains. However, solubilization of PUFAs could also be achieved by aqueous cyclodextrin (CD) solutions, which allowed us to avoid organic solvents. CDs are cyclic oligosaccharides consisting of 6, 7 or 8 glucopyranose units (α

• Toll-like receptor 3 (TLR3) specific for double stranded RNA (dsRNA). To avoid the interaction with cholesterol in the DC membrane in our in vitro experiments we used a non-cholesterol interacting CD, i.e., randomly methylated α-CD (RAMEA) for solubilization of n−3 PUFAs. Results and Discussion

Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs

• Lisa F. Becker,
• Dennis H. Schwarz and
• Gerhard Wenz

Beilstein J. Org. Chem. 2014, 10, 2920–2927, doi:10.3762/bjoc.10.310

• -CD [4][5], while β-CD shows some toxic effects such as haemolysis at high concentrations [6]. CDs are generally employed to increase the bioavailability of those APIs scarcely soluble in water [7]. The observed solubilization of an API is generally based on the complexation of the hydrophobic part of

Cyclodextrin–polysaccharide-based, in situ-gelled system for ocular antifungal delivery

• Anxo Fernández-Ferreiro,
• Noelia Fernández Bargiela,
• María Santiago Varela,
• Maria Gil Martínez,
• Maria Pardo,
• Antonio Piñeiro Ces,
• José Blanco Méndez,
• Miguel González Barcia,
• Maria Jesus Lamas and
• Francisco.J. Otero-Espinar

Beilstein J. Org. Chem. 2014, 10, 2903–2911, doi:10.3762/bjoc.10.308

• good candidates for the development of hydrogels. In this work, we have chosen HPBCD to solubilize fluconazole because although it showed comparable cytotoxicity effects compared to SBECD over short exposure periods, it has a lower molecular weight, and therefore, higher drug solubilization capacity

Synthesis of nanodiamond derivatives carrying amino functions and quantification by a modified Kaiser test

• Gerald Jarre,
• Steffen Heyer,
• Elisabeth Memmel,
• Thomas Meinhardt and
• Anke Krueger

Beilstein J. Org. Chem. 2014, 10, 2729–2737, doi:10.3762/bjoc.10.288

• situ. The reaction with the nanodiamond surface occurs simultaneously as soon as the diene is formed. The solvent dichlorobenzene was chosen not only for its suitable boiling point but also for the efficient solubilization of the reaction participants. The ND conjugate 9 shows characteristic signals in

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

• Véronique Nardello-Rataj and
• Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

• solubilization of CDs in water. In contrast, the cavity has a hydrophobic character due to carbons and ethereal oxygen atoms and allows the formation of inclusion complexes with hydrophobic molecules [3][4][5]. This property is useful to solubilize and to stabilize highly hydrophobic molecules in aqueous

Synthesis and characterization of a hyper-branched water-soluble β-cyclodextrin polymer

• Francesco Trotta,
• Fabrizio Caldera,
• Roberta Cavalli,
• Andrea Mele,
• Carlo Punta,
• Lucio Melone,
• Franca Castiglione,
• Barbara Rossi,
• Monica Ferro,
• Vincenza Crupi,
• Domenico Majolino,
• Valentina Venuti and
• Dominique Scalarone

Beilstein J. Org. Chem. 2014, 10, 2586–2593, doi:10.3762/bjoc.10.271

• at 450 nm, consistent with the formation of a SF/polymer complex. The solubilization capacity of the new branched β-CD polymer was also evaluated toward a very poor water soluble anticancer drug, i.e., paclitaxel, showing a great improvement in dispersion in water (data not shown). Conclusion A new

Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions

• Anne-Katrin Späte,
• Verena F. Schart,
• Julia Häfner,
• Andrea Niederwieser,
• Thomas U. Mayer and
• Valentin Wittmann

Beilstein J. Org. Chem. 2014, 10, 2235–2242, doi:10.3762/bjoc.10.232

• centrifugation (5 min, 400g). The cells were lysed in lysis buffer (400 µL) containing Triton X-100 (0.5%) (for permeabilization of membranes and solubilization of proteins and to prevent aggregate formation), DNase (30 µg mL−1), RNase (30 µg mL−1), β-glycerophosphate (20 mM) (Ser/Thr phosphatase inhibitor

A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, β-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges

• Martin Popr,
• Simona Hybelbauerová and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2014, 10, 1390–1396, doi:10.3762/bjoc.10.142

• [3]. The main areas of use of native CDs and their derivatives are drug transportation [4] and solubilization [5], catalysis [6] and enzyme mimics [7]. Chemically modified CDs [5][8] are prepared in order to reach specific chemical and physical properties, e.g., solubility or their binding behavior

Atherton–Todd reaction: mechanism, scope and applications

• Stéphanie S. Le Corre,
• Mathieu Berchel,
• Hélène Couthon-Gourvès,
• Jean-Pierre Haelters and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2014, 10, 1166–1196, doi:10.3762/bjoc.10.117

• second protocol (Scheme 23-ii) is almost similar to the first one except that a hydrochloride salt (e.g., ethylamine hydrochloride) was used as a substrate without prior solubilization in water. Finally, for the third protocol (Scheme 23-iii), the phosphinous acid is added to a mixture of the other

Stability of SG1 nitroxide towards unprotected sugar and lithium salts: a preamble to cellulose modification by nitroxide-mediated graft polymerization

• Guillaume Moreira,
• Laurence Charles,
• Mohamed Major,
• Florence Vacandio,
• Yohann Guillaneuf,
• Catherine Lefay and
• Didier Gigmes

Beilstein J. Org. Chem. 2013, 9, 1589–1600, doi:10.3762/bjoc.9.181

• SG1-based BlocBuilder MA alkoxyamine onto the acrylate function. Nevertheless, in the case of cellobiose the first step of acroylation has to be performed in DMA with a minimal amount of LiCl to ensure the cellobiose solubilization. The cello-SG1 alkoxyamine was then used to initiate the NMP of

Space filling of β-cyclodextrin and β-cyclodextrin derivatives by volatile hydrophobic guests

• Sophie Fourmentin,
• Anca Ciobanu,
• David Landy and
• Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1185–1191, doi:10.3762/bjoc.9.133

• superior to native β-CD. Thus, it was desirable to work with pure β-CD derivatives showing higher affinities. We reported recently the synthesis and use of heptafunctional 6-S-substitued CD derivatives 3 and 4 (Figure 1) for the solubilization of sparingly water-soluble drugs [32][33]. These β-CD

• -thioethers are single pure compounds and they showed very promising binding constants and very high aqueous solubility. In continuation of our investigations into the recognition of volatile organic compounds (VOCs) by CDs [34][35], we examined the potential of these β-CD-thioethers for the solubilization of

• good candidates for the solubilization of volatile hydrophobic compounds, because they are soluble in water at any concentration. Very high binding constants are obtained by attachment of hydrophobic substituents at both host and guest. However, substitution of CDs has to be performed at the primary

Influence of intramolecular hydrogen bonds on the binding potential of methylated β-cyclodextrin derivatives

• Gerhard Wenz

Beilstein J. Org. Chem. 2012, 8, 1890–1895, doi:10.3762/bjoc.8.218

• ]. The host–guest complexes, so-called cyclodextrin inclusion compounds, find many applications such as solubilization of pharmaceutical drugs, dispersion of cosmetics, catalysis, or chromatographic separation of enantiomers [2][7][8]. Application of β-CD 1 is hampered by its low solubility of 18.8 g L−1

Molecular solubilization of fullerene C₆₀ in water by γ-cyclodextrin thioethers

• Hai Ming Wang and
• Gerhard Wenz

Beilstein J. Org. Chem. 2012, 8, 1644–1651, doi:10.3762/bjoc.8.188

• with C60. Particle sizes of C60 were determined by dynamic light scattering. Keywords: C60; cyclodextrins; dynamic light scattering; particle size; solubilization; UV spectrum; Introduction Since the first spectroscopic discovery of buckminsterfullerene, C60, by Kroto, Heath, Curl and Smalley in 1985

• tendency to form nanoparticular aggregates [21][32], both of which limit their practical application. Recently, we developed a new class of highly water-soluble per-6-deoxy-thioethers of β- and γ-CD (>20% w/w), which showed exceptionally high solubilization abilities for several aromatic molecules, such as

• anthracene and acenaphthylene, in water [33][34][35]. In this work, we investigated solubilization of C60 by these γ-CD thioethers (compounds 1–7 in Scheme 1) with the hope of achieving high concentrations of solubilized C60. The hydrophilic substituents at the primary face of γ-CD should increase solubility

Highly selective synthesis of (E)-alkenyl-(pentafluorosulfanyl)benzenes through Horner–Wadsworth–Emmons reaction

• George Iakobson and
• Petr Beier

Beilstein J. Org. Chem. 2012, 8, 1185–1190, doi:10.3762/bjoc.8.131

• increased the reaction rate, presumably by better solubilization of KOH and the formed potassium diethylphosphate, and gave the required product 5a in 84% isolated yield and high E/Z selectivity (Table 1, entry 13). Using optimized reaction conditions (Table 1, entry 13), the scope of the HWE reaction of

Novel multi-responsive P2VP-block-PNIPAAm block copolymers via nitroxide-mediated radical polymerization

• Cathrin Corten,
• Katja Kretschmer and
• Dirk Kuckling

Beilstein J. Org. Chem. 2010, 6, 756–765, doi:10.3762/bjoc.6.89

• -dependent solution behavior, only block copolymers with a high P2VP content showed pH sensitivity. Solubilization of such polymers was possible below pH 5 only due to the protonation of pyridine moieties. In Figure 7 the solution behavior of such polymers is demonstrated. Figure 7a shows that the P2VP

Recognition properties of receptors consisting of imidazole and indole recognition units towards carbohydrates

• Monika Mazik and
• André Hartmann

Beilstein J. Org. Chem. 2010, 6, No. 9, doi:10.3762/bjoc.6.9

• -carbaldehyde (19) CH3OH, 3 d; h) 8 equiv of NaBH4, 0 °C to r. t., 12 h (78% of 4, 92% of 5). Solubilization of sugars in CDCl3 by receptor 4 and 5 (1 mM solution). Change in chemical shifta observed during 1H NMR titrations of receptor 4 or 5 with sugar 6a, 7a, 8a or 11 in CDCl3. Association constantsa,b for