BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

• Ludmila Škorpilová,
• Silvie Rimpelová,
• Michal Jurášek,
• Miloš Buděšínský,
• Jana Lokajová,
• Roman Effenberg,
• Petr Slepička,
• Tomáš Ruml,
• Eva Kmoníčková,
• Pavel B. Drašar and
• Zdeněk Wimmer

Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128

• . Specific drug targeting can be achieved by using, for example, antibodies, peptides, polyethylene glycol polymers, and last but not least, liposomes, which have been nowadays extensively investigated [1][2]. In general, liposomes are employed in order to enhance the therapeutic index of an applied drug by

Strategies toward protecting group-free glycosylation through selective activation of the anomeric center

• A. Michael Downey and
• Michal Hocek

Beilstein J. Org. Chem. 2017, 13, 1239–1279, doi:10.3762/bjoc.13.123

Phosphorus pentasulfide mediated conversion of organic thiocyanates to thiols

• Chandra Kant Maurya,
• Avik Mazumder and
• Pradeep Kumar Gupta

Beilstein J. Org. Chem. 2017, 13, 1184–1188, doi:10.3762/bjoc.13.117

• potassium thiocyanate in refluxing propylene glycol [19]. Simple short chain thiocyanates were found to react rapidly to give the corresponding thiols. In comparison to the alkyl substrates, the benzyl derivative reacted sluggishly possibly due to electronic effects which was further evident by the longer

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• intracellular stability. Liz-Marzan et al. assessed the ability of glycan ligands to reduce the protein corona formation around rod-shaped AuNPs [71]. Lactose- and polyethylene glycol (PEG)-functionalized gold nanorods demonstrated similar ability in reducing the interaction with proteins, when compared to

• protein component. In a different example, Barchi and co-workers focused on the Thomsen Friedenreich tumor-associated antigen (TFag) and synthesized TFag-amino acid-coated AuNPs by means of a thiol-polyethylene glycol spacer. Among the synthesized GAuNPs, TFag-Thr-AuNPs showed, in vitro, an increased

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

• , synthesized from polymer 8 (Scheme 3) through Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) with the triethylene glycol linker 11 (N3-TEG-NH2) which had been prepared in a five-step procedure [62][63]. Probing multivalent interactions by AFM The adhesive forces of 12, due to supramolecular interactions

Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

• Adrián A. Heredia and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2017, 13, 910–918, doi:10.3762/bjoc.13.92

• , we performed a screening of solvents under oxygen atmosphere (Table 1). Best yields were obtained with DMF, isopropanol or polyethylene glycol (PEG) as the solvents (Table 1, entries 1, 10, 12 and 13), whereas only moderate yields below 50% were obtained when the reaction was conducted in

Expression, purification and structural analysis of functional GABA transporter 1 using the baculovirus expression system

• Jing Hu,
• Chris Weise,
• Christoph Böttcher,
• Hua Fan and
• Jian Yin

Beilstein J. Org. Chem. 2017, 13, 874–882, doi:10.3762/bjoc.13.88

• glycans on the activity of the GAT1 protein, the glycol-engineered insect cells coupled with the baculovirus system may be further applied to produce a GAT1/GFP protein with complex, terminally sialylated N-glycans. Further structural analysis of the GAT1/GFP fusion protein is possible using

Energy down converting organic fluorophore functionalized mesoporous silica hybrids for monolith-coated light emitting diodes

• Markus Börgardts and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 768–778, doi:10.3762/bjoc.13.76

• , 9, and 10 were mixed in ethanol in a ratio of 1:6:17 furnishing a perfect white emission with the CIE chromaticity coordinates of x = 0.33 and y = 0.33. This mixture was then mixed with TEOS (tetraethoxysilane), surfactant P123 (poly(ethylene glycol)-poly(propylene glycol)-poly(ethylene glycol/(EtO

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• glucose, this particular monosaccharide has been extensively used as an ideal carbon source for CD formation, under a range of experimental conditions. The microwave-assisted synthesis of FCDs from a glucose solution in the presence of poly(ethylene glycol)-200 (PEG-200) by Yang et al. is, to the best of

• ]. It was found that irradiation times of 14 min could be employed to afford CDs from glycerol, glycol, glucose or sucrose. The source of the inorganic ion was important too, as increasing the valency of either the anion or cation would lead to a greater ability to dehydrate the carbon precursor. An

Transition-metal-catalyzed synthesis of phenols and aryl thiols

• Yajun Liu,
• Shasha Liu and
• Yan Xiao

Beilstein J. Org. Chem. 2017, 13, 589–611, doi:10.3762/bjoc.13.58

• nucleophilic substitution [39]. In 2015, the Chae group found difunctionalized ethanes including 2-dimethylaminoethanol and ethylene glycol can function as ligand to work with Cu(OAc)2 in the presence of KOH, affording phenols from aryl iodides in moderate to excellent yields (Scheme 17) [40]. In 2010, a

• 2015, on the basis of a successful application of ethylene glycol in a phenol synthesis [39], the Chae group developed a single-step protocol for the direct synthesis of aryl thiols. The protocol employed CuSO4·5H2O as the catalyst and KOH or Cs2CO3 as bases, and could convert aryl iodides, and aryl

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation

• Wangkhem P. Singh and
• Rajkumar S. Singh

Beilstein J. Org. Chem. 2017, 13, 138–149, doi:10.3762/bjoc.13.17

• summarized in Table 1. Three of the compounds (TPM-G4, TPM-G5, TPM-G12) formed organogels in polar solvents like dimethylsulfoxide (DMSO), propan-1-ol, propan-2-ol, butan-1-ol, butan-2-ol, diethylene glycol, and triethylene glycol. TPM-G5 (trityl derivative of 1-hexadecanol) formed an organogel in DMSO while

• TPM-G4 (trityl derivative of 1-tetradecanol) was able to gel diethylene glycol and triethylene glycol (Figure 1). TPM-G12 (the ditrityl derivative of 1,8-octanediol) turned out to be an excellent gelator of some polar solvents. It formed gels in DMSO, propan-1-ol, propan-2-ol, butan-1-ol, and butan-2

• loss of the entrapped solvent from the gels. TPM-G5 also formed a strong gel in DMSO which is stable at room temperature for a long time (≈2 weeks). In contrast, organogels formed from TPM-G4 in diethylene glycol and triethylene glycol were weak and not stable at prolonged storage (≈2 days). This is

Diels–Alder reactions of myrcene using intensified continuous-flow reactors

• Christian H. Hornung,
• Miguel Á. Álvarez-Diéguez,
• Thomas M. Kohl and
• John Tsanaktsidis

Beilstein J. Org. Chem. 2017, 13, 120–126, doi:10.3762/bjoc.13.15

• myrcene (1, 90% purity), maleic anhydride (2a), acrylic acid (2b), itaconic acid (2c), dimethyl maleate (2d), ethyl acrylate (2f) and poly(ethylene glycol) methyl ether acrylate (PEGA, 2g) were obtained from Sigma-Aldrich; bis(2-ethylhexyl) maleate was provided by TriTech Lubricants. The solvents

Poly(ethylene glycol)s as grinding additives in the mechanochemical preparation of highly functionalized 3,5-disubstituted hydantoins

• Andrea Mascitti,
• Massimiliano Lupacchini,
• Ruben Guerra,
• Ilya Taydakov,
• Lucia Tonucci,
• Nicola d’Alessandro,
• Frederic Lamaty,
• Jean Martinez and
• Evelina Colacino

Beilstein J. Org. Chem. 2017, 13, 19–25, doi:10.3762/bjoc.13.3

Versatile synthesis of end-reactive polyrotaxanes applicable to fabrication of supramolecular biomaterials

• Atsushi Tamura,
• Asato Tonegawa,
• Yoshinori Arisaka and
• Nobuhiko Yui

Beilstein J. Org. Chem. 2016, 12, 2883–2892, doi:10.3762/bjoc.12.287

• polyrotaxanes (PRXs) with reactive functional groups at the terminals of the axle polymers are attractive candidates for the design of supramolecular materials. Herein, we describe a novel and simple synthetic method for end-reactive PRXs using bis(2-amino-3-phenylpropyl) poly(ethylene glycol) (PEG-Ph-NH2) as

• simple synthesis method for end-reactive PRXs using commercially available 4-substituted benzoic acids. Typically, 4-substituted benzoic acids are unsuitable for the capping of pseudopolyrotaxanes because they are insufficiently bulky. In this study, bis(2-amino-3-phenylpropyl) poly(ethylene glycol) (PEG

• -catalyzed click reactions are performed. Additionally, fluorescence labeling of the PRX and intracellular fluorescence imaging were performed as an example application. Results and Discussion Synthesis of azide-terminated PRXs using bis(2-amino-3-phenylpropyl) poly(ethylene glycol) and 4-substituted benzoic

Biochemical and structural characterisation of the second oxidative crosslinking step during the biosynthesis of the glycopeptide antibiotic A47934

• Veronika Ulrich,
• Clara Brieke and
• Max J. Cryle

Beilstein J. Org. Chem. 2016, 12, 2849–2864, doi:10.3762/bjoc.12.284

• -function relationship of StaF, we attempted to structurally characterise the protein. We were able to determine the crystal structure of StaF to a resolution of 2.1 Å and 2.2 Å using different cryo-protectant solutions (ethylene glycol and glycerol) and by solving the phase problem through molecular

• for analysis (PDB ID: 5EX8; ethylene glycol cryo-protectant solution). The StaF structure is well resolved and adopts the typical structure of a cytochrome P450 [34], which consists predominantly of α-helices (12 in total: labelled A to L, including two additional helices labelled A’ and J’, Figure 5A

• (≈150 µm length) had formed. The crystals were passed through a cryoprotectant solution (0.1 M phosphate/citrate buffer (pH 4.2), 1.2 M Na2PO4, 0.3 M K2HPO4 and either 25% (v/v) glycerol, or 25% (v/v) ethylene glycol) and then flash cooled in liquid nitrogen for data collection. Two native data sets

Formose reaction controlled by boronic acid compounds

• Toru Imai,
• Tomohiro Michitaka and
• Akihito Hashidzume

Beilstein J. Org. Chem. 2016, 12, 2668–2672, doi:10.3762/bjoc.12.263

• six-carbon sugar alcohols (ethylene glycol, glycerol, erythritol, D-arabinitol, and D-mannitol, respectively) (Figure 2a). In Figure 2b–d, the signals at ca. 5 min may be due to impurities, e.g., inorganic salts. As can be seen in Figure 2b, the HPLC chart for the formose reaction in the absence of

Formose reaction accelerated in aerosol-OT reverse micelles

• Makoto Masaoka,
• Tomohiro Michitaka and
• Akihito Hashidzume

Beilstein J. Org. Chem. 2016, 12, 2663–2667, doi:10.3762/bjoc.12.262

• reaction using formaldehyde-13C as starting material are indicative of the formation of ethylene glycol as a major product. Keywords: aerosol-OT; formose reaction; hexadecyltrimethylammonium bromide; interfacial layer; reverse micelles; triton X-100; water pool; Findings The ‘formose reaction’ yields a

• acetonitrile, the internal standard, respectively. All the spectra contain two intense signals at ca. 63 and 75 ppm, although the ratios of signal intensities are different at different temperatures. The signal at ca. 63 ppm can be assigned to ethylene glycol, which may be derived from glycolaldehyde through

• Cannizzaro reaction. (We could not assign the signal at ca. 75 ppm comparing to signals for various sugar and sugar alcohols.) On the basis of these spectra, we can conclude that ethylene glycol is formed as a major product. In summary, the formose reaction in reverse micelles of AOT, TX, and CTAB was

A self-assembled cyclodextrin nanocarrier for photoreactive squaraine

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2016, 12, 2535–2542, doi:10.3762/bjoc.12.248

• -assembled from amphiphilic cyclodextrin [27]. Given their negligible toxicity cyclodextrins have been utilized as carriers in a number of studies [28][29]. Amphiphilic cyclodextrins substituted with hydrophobic alkyl groups on the primary side and hydrophilic oligo(ethylene glycol) units on the secondary

• . Amphiphilic β-cyclodextrins substituted with 7 dodecylsulfide groups on the primary side and 7 oligo(ethylene glycol) units on the secondary side were obtained via a straightforward three step synthesis as described [27][30]. A thin film of these amphiphiles was obtained by evaporation of a chloroform

Isosorbide and dimethyl carbonate: a green match

• Fabio Aricò and
• Pietro Tundo

Beilstein J. Org. Chem. 2016, 12, 2256–2266, doi:10.3762/bjoc.12.218

• conditions at the reflux temperature of DMC, methyl derivatives were either not observed or formed in small amount (Scheme 6). In particular, 2-octanol gave only the carboxymethyl derivative, meanwhile the methyl derivatives of propylene glycol propyl ether and 3-hydroxytetrahydrofuran formed only in scarce

The direct oxidative diene cyclization and related reactions in natural product synthesis

• Juliane Adrian,
• Leona J. Gross and
• Christian B. W. Stark

Beilstein J. Org. Chem. 2016, 12, 2104–2123, doi:10.3762/bjoc.12.200

• reaction; cf. Scheme 3). In this case the diol and the metal oxide form a glycol ester intermediate which then undergoes an intramolecular oxidative addition to a remote double bond. Thereby, type B oxidative cyclizations converge to the same (or very similar) reactive intermediate as is passed through in

• succeeded in synthesizing cis-solamin A (29) utilizing a ruthenium tetroxide-catalyzed type A oxidative cyclization approach (Scheme 9) [80]. Silyl-protected dienediol 34, the oxidative cyclization precursor, was synthesized from all-trans-cyclododecatriene 33 in four steps including dihydroxylation, glycol

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

• Maurizio Selva,
• Alvise Perosa,
• Sandro Guidi and
• Lisa Cattelan

Beilstein J. Org. Chem. 2016, 12, 1911–1924, doi:10.3762/bjoc.12.181

• phosphines and amines by dimethyl carbonate (Q = N, P). Bottom: anion metathesis of methyl carbonate onium salts. Synthesis of the acid polymeric IL. EGDMA: ethylene glycol dimethacrylate. The transesterification of sec-butyl acetate with MeOH catalyzed by some acidic imidazolium ILs. Top: phosgenation of

Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters

• Élise Euvrard,
• Nadia Morin-Crini,
• Coline Druart,
• Justine Bugnet,
• Bernard Martel,
• Cesare Cosentino,
• Virginie Moutarlier and
• Grégorio Crini

Beilstein J. Org. Chem. 2016, 12, 1826–1838, doi:10.3762/bjoc.12.172

• for the use of carboxylic acids and pyromellitic dianhydride, respectively, as agents to cross-linking CDs. Other cross-linking agents such as epichlorohydrin, ethylene glycol diglycidyl ether, glutaraldehyde, benzoquinone or isocyanates can be also used [1][12]. The main objective of the study was to

Organic chemistry meets polymers, nanoscience, therapeutics and diagnostics

• Vincent M. Rotello

Beilstein J. Org. Chem. 2016, 12, 1638–1646, doi:10.3762/bjoc.12.161

• the "tabula rasa" ligand [43], namely a ligand that features a hydrophobic interior for self-assembly, and a short tetra(ethylene glycol) layer to block interactions of the hydrophobic interiors with proteins [44]. These particles were indeed "blank" (but not as blank as our later zwitterionic “corona

• -free’ particles [45]), and behaved like high molecular weight poly(ethylene glycol) [46]. Once we appended simple anionic and cationic recognition elements to the surface these system bound proteins with high affinity [47] and some degree of selectivity [48]. What was surprising is that not only did

From N-vinylpyrrolidone anions to modified paraffin-like oligomers via double alkylation with 1,8-dibromooctane: access to covalent networks and oligomeric amines for dye attachment

• Daniela Obels,
• Melanie Lievenbrück and
• Helmut Ritter

Beilstein J. Org. Chem. 2016, 12, 1395–1400, doi:10.3762/bjoc.12.133

• poly(ethylene glycol) side chains. Keywords: double alkylation; modified N-vinylpyrrolidone; oligomeric anthraquinone dye; paraffin-like oligomer; radical thiol-ene click reaction; Introduction Poly(N-vinylpyrrolidone) (PVP) is established in daily life due to its high water solubility and

• Jeffamine® M 600 leads to blue-colored branched oligomer 6 with poly(ethylene glycol) side chains. The conducted reaction sequence is shown in Scheme 2. The quantitative conversion of the double bonds of oligomer 2a was verified by 1H NMR spectroscopy. As described above, the corresponding product 4 bears

• substituent of the attached anthraquinone moiety in 5 was replaced at elevated temperature with O-(2-aminopropyl)-O'-(2-methoxyethyl)propylene glycol (Jeffamine® M 600) yielding the branched blue-colored oligomeric dye 6. The deep blue color is a result of the presence of two amino groups in 1,4-position of