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

• analyzed using the Gallios software (Beckman-Coulter). Statistical analysis One way analysis of variance (ANOVA) was used to analyze the data (GraphPad software). Bonferroni post test was used when appropriate. P values < 0.05 were considered significant. Graphic representation of the bacterial adherence

• to inert substrata (A) and biofilms developed after 24 h, 48 h and 72 h of incubation (B) in the presence of 20 µM purified QSSMs (*P < 0.05, based on ANOVA and Bonferroni post test of medians of 3 independent experiments performed in triplicate). Graphic representation of the adherence index to

Carbonylonium ions: the onium ions of the carbonyl group

• Daniel Blanco-Ania and
• Floris P. J. T. Rutjes

Beilstein J. Org. Chem. 2018, 14, 2568–2571, doi:10.3762/bjoc.14.233

• group with mercury to a double bond. “Oxycarbenium ion” can also be found in the literature with this meaning that it correctly describes the same intermediate, although not the more realistic representation of it [30]. Carboxonium ions Other research groups, e.g., Olah’s and Prakash’s, have used the

Learning from B₁₂ enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

• Keishiro Tahara,
• Ling Pan,
• Toshikazu Ono and
• Yoshio Hisaeda

Beilstein J. Org. Chem. 2018, 14, 2553–2567, doi:10.3762/bjoc.14.232

• systems in terms of green and eco-friendly reactions. (a) Structure and (b) reactivity of B12. (a) Schematic representation of B12 enzyme-involving systems. (b) Construction of biomimetic and bioinspired catalytic systems by combining functional equivalents of B12 enzyme-involving systems as components

Comparative cell biological study of in vitro antitumor and antimetastatic activity on melanoma cells of GnRH-III-containing conjugates modified with short-chain fatty acids

• Eszter Lajkó,
• Sarah Spring,
• Rózsa Hegedüs,
• Beáta Biri-Kovács,
• Sven Ingebrandt,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 2495–2509, doi:10.3762/bjoc.14.226

• frames. The levels of significance are shown as follows *: p < 0.05; ***: p < 0.001. Schematic representation of the proposed mechanisms of the effects of GnRH-III conjugates containing acylated 4Lys in A2058 melanoma cell line. Dau: daunorubicin. Analytical characteristics of Dau–GnRH-III conjugates

Some mechanistic aspects regarding the Suzuki–Miyaura reaction between selected ortho-substituted phenylboronic acids and 3,4,5-tribromo-2,6-dimethylpyridine

• Piotr Pomarański,
• Piotr Roszkowski,
• Jan K. Maurin,
• Armand Budzianowski and
• Zbigniew Czarnocki

Beilstein J. Org. Chem. 2018, 14, 2384–2393, doi:10.3762/bjoc.14.214

• stereoisomers of 3,4,5-tris(2-methoxyphenyl)-2,6-dimethylpyridines determined by X-ray analysis [38]. Graphical representation of kinetic, time-dependent 1H NMR analysis of (syn)-7 (100 °C). Graphical representation of kinetic, time-dependent 1H NMR analysis of (syn)-10 (120 °C). HT-NMR (300 MHz, DMSO-d6

Bioinspired cobalt cubanes with tunable redox potentials for photocatalytic water oxidation and CO₂ reduction

• Zhishan Luo,
• Yidong Hou,
• Jinshui Zhang,
• Sibo Wang and
• Xinchen Wang

Beilstein J. Org. Chem. 2018, 14, 2331–2339, doi:10.3762/bjoc.14.208

• -1 mesh 42/10); Argon was used as the carrier gas. (a) Molecular structures of the Co4O4 cubane catalysts. (b) Ball-and-stick representation of complex 1-H; H atoms are omitted for clarity. UV–vis absorption spectra of 1-R in H2O based on measurements in 10−4 M solution. Inset: scale from 400 nm to

Determining the predominant tautomeric structure of iodine-based group-transfer reagents by ¹⁷O NMR spectroscopy

• Nico Santschi,
• Cody Ross Pitts,
• Benson J. Jelier and
• René Verel

Beilstein J. Org. Chem. 2018, 14, 2289–2294, doi:10.3762/bjoc.14.203

• represent 4c in solution. Does the compound resemble the molecular structure obtained in the solid state with oxygen still coordinated to iodine or would a free alcohol be a more accurate representation? In order to generate 4c, reagent 4a was treated with five equivalents of trifluoroacetic acid (TFA) and

• minimum reminiscent of the pictographic representation of 4c with an intact but significantly elongated I–O bond of 2.55 Å (Figure 3) and qualitatively, the NMR data are in support of this notion. From a quantitative point of view, the data points (δiso, δobs) for 1, 4b, and 4c afforded a perfect linear

• correlation with R2 = 1, thus lending further credence to the representation of the protonated form 4a in solution as 4c (see Supporting Information File 1). Conclusion In summary, the present study demonstrates that 17O NMR spectroscopy at natural abundance coupled with DFT-calculated isotropic shift values

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

• -thiacyclophane 6: (a) ball-and-stick representation, with O–H···S hydrogen bonds shown as green dashed lines, (b) space-filling representation viewed along the pseudo twofold axis. Macrocyclization towards homothiacalixarenes 3a and 3b [12]. Cyclocondensation reaction of 4 and 5 towards [2 + 2] and [3 + 3

Tetrathiafulvalene – a redox-switchable building block to control motion in mechanically interlocked molecules

• Hendrik V. Schröder and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2018, 14, 2163–2185, doi:10.3762/bjoc.14.190

• states of 19. Schematic representation of a molecular electronic memory based on a bistable TTF-based rotaxane. (a) Molecular structure of the amphiphilic [2]rotaxane 20. (b) Structure of the crossbar device. (c) Switching mechanism of rotaxane 20 in a junction. Schematic representation of bending motion

• representation

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

Calix[6]arene-based atropoisomeric pseudo[2]rotaxanes

• Carmine Gaeta,
• Carmen Talotta and
• Placido Neri

Beilstein J. Org. Chem. 2018, 14, 2112–2124, doi:10.3762/bjoc.14.186

• pseudorotaxane (b). Cartoon representation of the chiral rotaxane of the Goldup group [15][16] (I and I*) and of the chiral pseudorotaxane (II and II*) reported by our group [17]. Cartoon representation of the rotaxane sequence isomers reported by Leigh [17] (III and IV) and of the pseudorotaxane sequential

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

• is used as a candidate to form a new chiro-optical system [30][36][37][38][39][40][41]. Ureidopyrimidinone (UPy), as a connection site, is also introduced to make quadruple hydrogen bonding [42][43][44]. The structure and schematic representation of 3 are shown in Figure 1. The possible assembly

• +, 763.3445; found, 763.3443. The chemical structure and the schematic representation of compound 3 as well as the proposed assembly process of the nanostructure. UV–vis absorbance spectra of a) compound 3 and b) irradiated by a light source of 365 nm and c) then treated by light of 420 nm. The concentration

An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point change

• Tomoki Ogoshi,
• Tomohiro Akutsu and
• Tada-aki Yamagishi

Beilstein J. Org. Chem. 2018, 14, 1937–1943, doi:10.3762/bjoc.14.167

• representation of neutral-guest responsive clouding point change using supramolecular structural change from pseudo[1]catenane to de-threaded form upon (b) addition of a competitive guest, 1,4-dicyanobutane. Synthesis of the bicyclic compound 3. Supporting Information Supporting Information File 348: 1H and 13C

Assessing the possibilities of designing a unified multistep continuous flow synthesis platform

• Mrityunjay K. Sharma,
• Roopashri B. Acharya,
• Chinmay A. Shukla and
• Amol A. Kulkarni

Beilstein J. Org. Chem. 2018, 14, 1917–1936, doi:10.3762/bjoc.14.166

• platform. Schematic representation of a unified platform for the flow synthesis (P1–P14 pumps, PBR packed bed reactor, HE1 heat exchanger, H1 heater, S1 and S2 separator, E1 extractor, TR1–TR4 tubular reactor, CH charcoal, CT1 crystallization tank, T1–T3 tanks, F1 filtration). Layout of a unified synthesis

Diazirine-functionalized mannosides for photoaffinity labeling: trouble with FimH

• Femke Beiroth,
• Tomas Koudelka,
• Thorsten Overath,
• Stefan D. Knight,
• Andreas Tholey and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1890–1900, doi:10.3762/bjoc.14.163

• of the mannoside are varied. In 5 a bis-diazirine functionalization is suggested to increase labeling probability. Connolly representation of photolabile α-D-mannoside 3 in the closed gate (A, PDB code 1UWF) and open gate crystal structure of FimH (B, PDB code 1KLF) [24]. The surface is colored

Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – a powerful hypervalent iodine(V) oxidant

• Irina A. Mironova,
• Pavel S. Postnikov,
• Rosa Y. Yusubova,
• Akira Yoshimura,
• Thomas Wirth,
• Viktor V. Zhdankin,
• Victor N. Nemykin and
• Mekhman S. Yusubov

Beilstein J. Org. Chem. 2018, 14, 1854–1858, doi:10.3762/bjoc.14.159

• the iodine(V) products. X-ray structure of an independent crystal unit of IBS 6-K. Simplified representation of structure 6-K. Selected interatomic distances (Å): I(1)=O(1) 1.79; I(1)=O(2) 1.81; I(1)–O(3) 2.54; O(2)–I(2) 2.46; I(2)=O(7) 1.81; I(2)–O(6) 1.88; I(2)–O(8) 2.60; I(2)–O(16) 2.71; I(3)=O(11

Defining the hydrophobic interactions that drive competence stimulating peptide (CSP)-ComD binding in Streptococcus pneumoniae

• Bimal Koirala,
• Robert A. Hillman,
• Erin K. Tiwold,
• Michael A. Bertucci and
• Yftah Tal-Gan

Beilstein J. Org. Chem. 2018, 14, 1769–1777, doi:10.3762/bjoc.14.151

• . A helical wheel representation of the CSP1 sequence revealed that, with the exception of L13, all the residues discussed above (4, 7, 8, 11 and 12) occupy the same face of the helix (Figure 4). This result suggests that only one face of the CSP1 helix is directly interacting with the ComD1 receptor

• wheel representation of CSP1. The CSP1 residues are presented using the one-letter amino acid code. The presentation reveals that, with the exception of L13, all the hydrophobic residues occupy the same face of the helix. Image produced using the NetWheels application (http://lbqp.unb.br/NetWheels

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

• Eirinaios I. Vrettos,
• Gábor Mező and
• Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

Local energy decomposition analysis of hydrogen-bonded dimers within a domain-based pair natural orbital coupled cluster study

• Ahmet Altun,
• Frank Neese and
• Giovanni Bistoni

Beilstein J. Org. Chem. 2018, 14, 919–929, doi:10.3762/bjoc.14.79

• (b) HF dimer. Schematic representation of strong pair excitations in the framework of the DLPNO-CCSD(T) method. Electronic preparation arises from excitations occurring within the same fragment, which are not shown. Only the charge transfer excitations from X to Y are shown. Analogous charge transfer

Crystal structure of the inclusion complex of cholesterol in β-cyclodextrin and molecular dynamics studies

• Elias Christoforides,
• Andreas Papaioannou and
• Kostas Bethanis

Beilstein J. Org. Chem. 2018, 14, 838–848, doi:10.3762/bjoc.14.69

• term is often problematic as the normal mode lacks information of the conformational entropy and alternative methods do not give converged results [51]. Thus, this term is usually omitted and the comparison between similar complexes is based on the ΔGGB solely. Schematic representation of (a) the

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

• representation of a Pickering emulsion with the enzyme in the water phase (i), or with the enzyme inside the polymersome lumen (ii). 3b) Chart of the specific activities of CalB dissolved in the water phase of the polymersome Pickering emulsion (left), CalB in a biphasic water/toluene system (middle,) and CalB

• encapsulated in the lumen of the polymersome Pickering emulsion (right). Adapted with permission from [79]. Cross-linked polymersomes with Cu(OTf)2 catalyst. Reprinted with permission from [15]. Schematic representation of enzymatic polymerization in polymersomes. (A) CALB in the aqueous compartment (B) CALB

• embedded in the bilayer. Reprinted with permission from [21]. Copyright 2007 American Chemical Society. Representation of DSN-G0. Reprinted with permission from [100]. The multivalent esterase dendrimer 5 catalyzes the hydrolysis of 8-acyloxypyrene 1,3,6-trisulfonates 6a–c. Reprinted with permission from

Enhanced quantum yields by sterically demanding aryl-substituted β-diketonate ancillary ligands

• Rebecca Pittkowski and
• Thomas Strassner

Beilstein J. Org. Chem. 2018, 14, 664–671, doi:10.3762/bjoc.14.54

• ); 195Pt NMR (CDCl3, 64.52 MHz) δ (ppm) −3383; ESIMS m/z = 688.4 [M + H]+; anal. calcd for C33H36N2O2Pt: C, 57.63; H, 5.28; N, 4.07; found: C, 57.93; H, 5.46; N, 3.82. ORTEP representation of 3. Thermal ellipsoids are drawn at the 50% probability level. Selected bond lengths (Å) and angles (deg): C(1)–Pt(1

High-yielding continuous-flow synthesis of antimalarial drug hydroxychloroquine

• Eric Yu,
• Hari P. R. Mangunuru,
• Nakul S. Telang,
• Caleb J. Kong,
• Jenson Verghese,
• Stanley E. Gilliland III,
• Saeed Ahmad,
• Raymond N. Dominey and
• B. Frank Gupton

Beilstein J. Org. Chem. 2018, 14, 583–592, doi:10.3762/bjoc.14.45

• were obtained in accordance with those previously reported [38][39]. Commercially available antimalarial drugs. Current batch syntheses of the key intermediate 5-(ethyl(2-hydroxyethyl)amino)pentan-2-one (6). Retrosynthetic strategy to hydroxychloroquine (1). Schematic representation for continuous in

• -line extraction of 10. Optimization of the flow process for the synthesis of 12. Optimization of the flow process for the synthesis of 10. Schematic representation for the continuous telescoped process to synthesize 11. Optimization of the flow process for the reductive amination of 12 using a CSTR

Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review

• Fabio Tonin and
• Isabel W. C. E. Arends

Beilstein J. Org. Chem. 2018, 14, 470–483, doi:10.3762/bjoc.14.33

• dehydroxylation reactions are highlighted with a red, blue and green arrow, respectively. Names of compounds are indicated in the box. The general stereoinformation of steroid scaffold is shown in Figure 2. R = 4-pentanoic acid. Schematic representation of the flow reactor for the continuous conversion of CDCA to