Application of olefin metathesis in the synthesis of functionalized polyhedral oligomeric silsesquioxanes (POSS) and POSS-containing polymeric materials

• Patrycja Żak and
• Cezary Pietraszuk

Beilstein J. Org. Chem. 2019, 15, 310–332, doi:10.3762/bjoc.15.28

• edges, chemically bonded with eight different or similar organic substituents so that it represents a truly hybrid architecture. The cubic silsesquioxane unit is characterized by a three-dimensional nanoscopic size structure with approximate Si–Si distance equal to 0.5 nm and an approximate R–R distance

Adhesion, forces and the stability of interfaces

• Robin Guttmann,
• Johannes Hoja,
• Christoph Lechner,
• Reinhard J. Maurer and
• Alexander F. Sax

Beilstein J. Org. Chem. 2019, 15, 106–129, doi:10.3762/bjoc.15.12

• metallic nanotubes with easily polarizable electron densities, and they are less frequently found in three-dimensional metals [35][37][38]. Delocalized density fluctuations allow for the induction of large dipoles or higher multipoles that enhance weak molecular interaction: It is characteristic of

Lectins of Mycobacterium tuberculosis – rarely studied proteins

• Katharina Kolbe,
• Sri Kumar Veleti,
• Norbert Reiling and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2019, 15, 1–15, doi:10.3762/bjoc.15.1

• Streptomyces olivaceoviridis) [77][78]. This secreted protein was crystallized in 2010 by Patra et al., however, a three-dimensional structure has yet to be resolved [79]. Recently Nogueira et al. detected high titers of IgG antibodies against sMTL-13 in sera from TB patients, a response found to be diminished

Ring-opening metathesis of some strained bicyclic systems; stereocontrolled access to diolefinated saturated heterocycles with multiple stereogenic centers

• Zsanett Benke,
• Melinda Nonn,
• Márton Kardos,
• Santos Fustero and
• Loránd Kiss

Beilstein J. Org. Chem. 2018, 14, 2698–2707, doi:10.3762/bjoc.14.247

• of attention in synthetic organic chemistry, affording access to various highly functionalized, alkenylated molecular entities [1][2][3][4][5][6][7][8][9][10]. Highly functionalized three-dimensional organic scaffolds with multiple stereogenic centers as small molecular entities represent an

• multiple stereogenic centers thus synthesized can be considered interesting scaffolds for further transformations in view of the access of novel three-dimensional functionalized scaffolds through cross-metathesis (CM). An illustrative example is shown on Scheme 7. Divinylated γ-lactam (±)-19 selected as a

• stereogenic centers. The resulting diolefinated aminolactones, isoxazolines or lactam derivatives with multiple stereogenic centers might be considered to be interesting highly-functionalized three-dimensional compounds for further derivatizations. Extensions of the ROM of various bicyclic, conformationally

Impact of Pseudomonas aeruginosa quorum sensing signaling molecules on adhesion and inflammatory markers in endothelial cells

• Carmen Curutiu,
• Florin Iordache,
• Veronica Lazar,
• Aurelia Magdalena Pisoschi,
• Aneta Pop,
• Mariana Carmen Chifiriuc and
• Alina Maria Hoban

Beilstein J. Org. Chem. 2018, 14, 2580–2588, doi:10.3762/bjoc.14.235

• deficient strains differ in size and stability of the structure, being more flexible due to the production of QS-regulated extracellular DNA [8], which acts as a stabilizer of three-dimensional biofilm structure [8]. In patients with cystic fibrosis, the growth of bacteria in biofilm determines aggravation

Calixazulenes: azulene-based calixarene analogues – an overview and recent supramolecular complexation studies

• Paris E. Georghiou,
• Shofiur Rahman,
• Abdullah Alodhayb,
• Hidetaka Nishimura,
• Jaehyun Lee,
• Atsushi Wakamiya and
• Lawrence T. Scott

Beilstein J. Org. Chem. 2018, 14, 2488–2494, doi:10.3762/bjoc.14.225

• relatively facile and reproducible syntheses of the classical calix[n]arenes 1 in which n = 4, 6 or 8, with phenolic groups linked or bridged via methylene groups to form defined three-dimensional basket-like cavities with “upper” or “lower” rims, were developed by Gutsche and co-workers [4][5][6]. As a

Nucleoside macrocycles formed by intramolecular click reaction: efficient cyclization of pyrimidine nucleosides decorated with 5'-azido residues and 5-octadiynyl side chains

• Jiang Liu,
• Peter Leonard,
• Sebastian L. Müller,
• Constantin Daniliuc and
• Frank Seela

Beilstein J. Org. Chem. 2018, 14, 2404–2410, doi:10.3762/bjoc.14.217

• = 173°) [48] adopt an anti-conformation [49]. The conformation of the 2’-deoxyribofuranosyl moiety of 8 shows an C3’-endo envelope pucker (4E, N-type) in the solid state with a pseudorotational phase angle P = 50.2(2)° and a maximum amplitude of τm = 38.7(1)°. The extended structure forms a three

• -dimensional network consisting of a linear unit connected by hydrogen bonds between N3–H and the triazole N3’’ of a second molecule (Figure 3, Supporting Information File 1, Figures S3 and S4). Additionally, the molecules are bridged by water molecules connecting O2 of the base moiety and N2’’ of the triazole

Synthesis and post-functionalization of alternate-linked-meta-para-[2ⁿ.1ⁿ]thiacyclophanes

• Wout De Leger,
• Koen Adriaensen,
• Koen Robeyns,
• Luc Van Meervelt,
• Joice Thomas,
• Björn Meijers,
• Mario Smet and
• Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 2190–2197, doi:10.3762/bjoc.14.192

• ; Introduction The ability of cyclophanes to form three-dimensional cavities is interesting for various potential applications, e.g., as supramolecular hosts. Synthetic procedures towards novel cyclophanes have attracted much interest in the scientific community [1][2][3][4]. An interesting subclass of

Evaluation of dispersion type metal···π arene interaction in arylbismuth compounds – an experimental and theoretical study

• Ana-Maria Preda,
• Małgorzata Krasowska,
• Lydia Wrobel,
• Philipp Kitschke,
• Phil C. Andrews,
• Jonathan G. MacLellan,
• Lutz Mertens,
• Marcus Korb,
• Tobias Rüffer,
• Heinrich Lang,
• Alexander A. Auer and
• Michael Mehring

Beilstein J. Org. Chem. 2018, 14, 2125–2145, doi:10.3762/bjoc.14.187

• of a neighboring molecule in a way that each bismuth atom interacts with three oxygen atoms of different neighbors. In the resulting three-dimensional structure, one molecule of 3 interacts with six other molecules (Figure 6b). Similar Bi···O interactions are also found in tris(2-methoxyphenyl)- and

A self-assembled photoresponsive gel consisting of chiral nanofibers

• Lei Zou,
• Dan Han,
• Zhiyi Yuan,
• Dongdong Chang and
• Xiang Ma

Beilstein J. Org. Chem. 2018, 14, 1994–2001, doi:10.3762/bjoc.14.174

• by three-dimensional networks through self-assembly have drawn significant attention in the past decades. They are normally fabricated by means of noncovalent intermolecular interactions [3], such as π–π stacking, hydrogen bonding, van der Waals forces, hydrophobic, electrostatic, host–guest and

Recent applications of chiral calixarenes in asymmetric catalysis

• Mustafa Durmaz,
• Erkan Halay and
• Selahattin Bozkurt

Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117

• Analysis Technological Application and Research Center (UBATAM), Usak University, Usak, Turkey Vocational School of Health Services, Usak University, 64200 Usak, Turkey 10.3762/bjoc.14.117 Abstract The use of calixarenes in asymmetric catalysis is receiving increasing attention due to their tunable three

• -dimensional molecular platforms along with their easy syntheses and versatile modification at the upper and lower rims. This review summarizes the recent progress of synthesis and use of chiral calixarenes in asymmetric syntheses which emerged later than 2010. Keywords: asymmetric catalysis; chiral

Nanoreactors for green catalysis

• M. Teresa De Martino,
• Loai K. E. A. Abdelmohsen,
• Floris P. J. T. Rutjes and
• Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

• tuned by varying their initial molecular components or the number of generations they possess [91][92]. They can assemble in a spherical shape, and within the three-dimensional structure, an interior void is present wherein to accommodate other molecules [93]. Catalysis in dendrimers: The controlled

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

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• composed of three isoindoline units. The only central element of subphthalocyanine is boron, and it has a ligand in the axial direction on the boron. Since subphthalocyanines have excellent spectroscopic properties and a unique three-dimensional structure, it is expected that they will be applied to

• various fields [126][127][128], alongside phthalocyanines. However, the solubility of subphthalocyanines is not very high despite of the non-aggregation phenomenon due to their three-dimensional structure. On the other hand, since trifluoroethoxy-substituted subphthalocyanines (TFEO-subPcs) have high

Conformational impact of structural modifications in 2-fluorocyclohexanone

• Francisco A. Martins,
• Josué M. Silla and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2017, 13, 1781–1787, doi:10.3762/bjoc.13.172

• , while organic fluorine plays a fundamental role in the design of performance organic molecules. Since these features are dependent on the three-dimensional chemical structure of a molecule, simple structural modifications can affect its conformational stability and, consequently, the corresponding

2-Methyl-2,4-pentanediol (MPD) boosts as detergent-substitute the performance of ß-barrel hybrid catalyst for phenylacetylene polymerization

• Julia Kinzel,
• Daniel F. Sauer,
• Marco Bocola,
• Marcus Arlt,
• Tayebeh Mirzaei Garakani,
• Andreas Thiel,
• Klaus Beckerle,
• Tino Polen,
• Jun Okuda and
• Ulrich Schwaneberg

Beilstein J. Org. Chem. 2017, 13, 1498–1506, doi:10.3762/bjoc.13.148

• can destroy the three dimensional structure and cause protein precipitation [19][20][21]. To avoid precipitation when using nonpolar substrates, the protein concentration usually is decreased leading to a loss in activity. As an example, the polymerization of phenylacetylene was achieved in water by

A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline

• Olga Bakulina,
• Alexander Ivanov,
• Vitalii Suslonov,
• Dmitry Dar’in and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2017, 13, 1413–1424, doi:10.3762/bjoc.13.138

• hexahydropyrrolo[1,2-b]isoquinolone derivatives fused with benzene 10 that have pronounced three-dimensional features and potentially contain several quaternary carbon centers (Figure 2). The first aspect has been recently recognized [29] as a central principle in drug design ensuring effective interaction of

Detection of therapeutic radiation in three-dimensions

• John A. Adamovics

Beilstein J. Org. Chem. 2017, 13, 1325–1331, doi:10.3762/bjoc.13.129

• John A. Adamovics Department of Chemistry, Biochemistry and Physics, Rider University, 2083 Lawrenceville Road, Lawrenceville, NJ 08648-3099, USA 10.3762/bjoc.13.129 Abstract For over the last twenty years there has been a multitude of sophisticated three-dimensional radiation delivery procedures

• developed which requires a corresponding verification of the impact on patients. This article reviews the state of the art in the development of chemical detectors used to characterize the three-dimensional shape of therapeutic radiation. These detectors are composed of polyurethane, radical initiator and a

• made in developing chemical-based three-dimensional radiation detection systems but as of this review these dosimeters are primarily used in clinical research settings. This is partially due to the lack of a viable commercially available OCT scanner and availability of alternative semi-3D radiation

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• the wavelength to reach the values that are optimum for a given experiment provides the most powerful way to determine the three-dimensional features of macromolecular structures. Diffraction performed at an energy close to a heavy element absorption edge produces a resonant effect for which scattered

• 1930, the first crystal structures of organic compounds to be investigated were carbohydrates of low molecular weight. Over the following years, only eight additional crystal structures were reported. The determination of the three dimensional structure of the dehydrated form of sucrose, in 1947, was

• technique’s high resolution, new possibilities exist, such as the investigations of the occurrence of phase transitions in large macromolecules as a function of temperature. Macromolecular structures X-ray diffraction with synchrotron radiation is the most powerful method for revealing the three-dimensional

From chemical metabolism to life: the origin of the genetic coding process

• Antoine Danchin

Beilstein J. Org. Chem. 2017, 13, 1119–1135, doi:10.3762/bjoc.13.111

• atomic composition of matter: N for nitrogen, Fe, for iron, C for carbon). Thus a chemical molecule is information-rich. sn-Glycerol-3-phosphate can be described, including an outline of its three-dimensional configuration, by a limited alphabet of symbols (e.g., the Simplified Molecular Input Line Entry

Total syntheses of the archazolids: an emerging class of novel anticancer drugs

• Stephan Scheeff and
• Dirk Menche

Beilstein J. Org. Chem. 2017, 13, 1085–1098, doi:10.3762/bjoc.13.108

• three dimensional conformation of the archazolids by NMR methods, molecular modelling and chemical derivatizations [59][60]. During these studies, they became aware that C2–C5 diene of acyclic analogs would be very labile towards isomerization. However, such processes would be suppressed in the

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

• protein, GAT1, is a potential drug target. The exact three-dimensional structure of GAT1 protein could provide more information for pharmaceutical research. The structural analysis of most membrane proteins is challenging since significant protein yields are required and because eukaryotic membrane

• crystallography, thereby improving our understanding of the three-dimensional structure of the GAT1 protein. Experimental Immunoprecipitation and Western blotting The immunoprecipitation and Western blotting procedures were similar to those described previously [12]. Briefly, the GAT1/GFP protein was solubilized

The effect of cyclodextrin complexation on the solubility and photostability of nerolidol as pure compound and as main constituent of cabreuva essential oil

• Joyce Azzi,
• Pierre-Edouard Danjou,
• David Landy,
• Steven Ruellan,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2017, 13, 835–844, doi:10.3762/bjoc.13.84

• narrow side of CD. Molecular modelling The theoretical molecular modelling is useful to illustrate the most energetically favorable three-dimensional structure of the inclusion complex in solution. The inclusion complex conformer that presents the weakest relative binding energies (ΔE) (i.e., the most

Continuous-flow processes for the catalytic partial hydrogenation reaction of alkynes

• Carmen Moreno-Marrodan,
• Francesca Liguori and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2017, 13, 734–754, doi:10.3762/bjoc.13.73

• substrate hindrance affects catalyst activity, even if not directly related to continuous flow operation conditions. It was proposed that ligand-modified surfaces, such as Pd(HHDMA)@C, are three-dimensional catalytic ensembles whose organic capping layer cannot be penetrated with ease by larger alkynes

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

• two adjacent linear arrays will be approximately equal to (or less than) the width of the TPM-G12 molecule (8.50 Å). Subsequently, different layers of these two-dimensional planar structures can aggregate together to give the three-dimensional microstructure of the gel. The distance between any two