Membrane properties of hydroxycholesterols related to the brain cholesterol metabolism

• Malte Hilsch,
• Ivan Haralampiev,
• Peter Müller,
• Daniel Huster and
• Holger A. Scheidt

Beilstein J. Org. Chem. 2017, 13, 720–727, doi:10.3762/bjoc.13.71

• constituents, resulting in highly characteristic effects on the packing and lateral organization of the membrane lipids and proteins [1][10][11][12][13]. Even very small alterations in the molecular structure of cholesterol cause large differences in the interaction with phospholipids and its membrane’s

Sulfamide chemistry applied to the functionalization of self-assembled monolayers on gold surfaces

• Loïc Pantaine,
• Vincent Humblot,
• Vincent Coeffard and
• Anne Vallée

Beilstein J. Org. Chem. 2017, 13, 648–658, doi:10.3762/bjoc.13.64

• the layer organization. Even if the reaction is not completely reversible, it is worth noting that the conversion rate of the hydrolysis in these mild conditions on the surface is as good as the one obtained in solution in the same conditions, e.g. 65%. While most of the previous works used only

Biosynthetic origin of butyrolactol A, an antifungal polyketide produced by a marine-derived Streptomyces

• Enjuro Harunari,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2017, 13, 441–450, doi:10.3762/bjoc.13.47

• -butyl group. Actinomycete metabolites possessing a contiguous 1,2-diol system. Feeding experiments of 13C-labeled precursors into 1 detected by 2D-INADEQUATE NMR experiments. (a) [1,2-13C2]acetate; (b) [U-13C6]glucose. Organization of the biosynthesis gene cluster for 1. Blue, transcriptional regulator

Versatile synthesis of the signaling peptide glorin

• Robert Barnett,
• Daniel Raszkowski,
• Thomas Winckler and
• Pierre Stallforth

Beilstein J. Org. Chem. 2017, 13, 247–250, doi:10.3762/bjoc.13.27

• actin cytoskeleton organization, as a model gene. Upon glorin (1) exposure, this gene was found to be up-regulated by about 50-fold [11]. To this end, the compounds were dissolved in DMSO/water and added in two 1 μM portions (30 min apart) to a suspension of starving P. pallidum. After 1 h, the cells

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

• chemistry have demonstrated that hydrogen bonds formed by C–H bonds are not necessarily “weak”, and in certain cases are almost as strong as more traditional A–H···A bonds [20]. The C–H hydrogen bonding between the substrate and the catalyst could be of great significance for transition state organization

Benzothiadiazole oligoene fatty acids: fluorescent dyes with large Stokes shifts

• Lukas J. Patalag and
• Daniel B. Werz

Beilstein J. Org. Chem. 2016, 12, 2739–2747, doi:10.3762/bjoc.12.270

• , SFB 803 “Functionality controlled by organization in and between membranes”, project A05) and the Fonds der Chemischen Industrie (FCI) for financial support (Dozentenstipendium to D.B.W.). We thank Martin Bröring (TU Braunschweig) for the possibility of measuring quantum yields by the instrument in

Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases

• Vladimir A. Stepchenko,
• Anatoly I. Miroshnikov,
• Frank Seela and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2016, 12, 2588–2601, doi:10.3762/bjoc.12.254

• ), respectively, towards the calf-spleen and E. coli PNPs and disclosed their satisfactory substrate activity [68]. The authors discussed the results in terms of similar spatial organization of natural nucleosides and their N-3-isomers admitting the binding and activation of the latter at the catalytic sites of

• not shown). Thus, both enzymes demonstrated severe restrictions on the bulkiness and three-dimensional structure of the substituent at the C-5 atom of the pyrimidines. The spatial organization of the very poor substrates 5-tert-butyluracil (15) and 5-phenyluracil (16) vs good substrates 5-ethyluracil

Effects of solvent additive on “s-shaped” curves in solution-processed small molecule solar cells

• John A. Love,
• Shu-Hua Chou,
• Ye Huang,
• Guilllermo C. Bazan and
• Thuc-Quyen Nguyen

Beilstein J. Org. Chem. 2016, 12, 2543–2555, doi:10.3762/bjoc.12.249

• deep energy levels, as well as some of the other desirable properties of the parent material [20][21][22]. However, molecular design remains only the first step towards the development of high performance devices. Mismanagement of the organization and phase-separation processes or inappropriate device

Protonated paramagnetic redox forms of di-o-quinone bridged with p-phenylene-extended TTF: A EPR spectroscopy study

• Nikolay O. Chalkov,
• Vladimir K. Cherkasov,
• Gleb A. Abakumov,
• Andrey G. Starikov and
• Viacheslav A. Kuropatov

Beilstein J. Org. Chem. 2016, 12, 2450–2456, doi:10.3762/bjoc.12.238

• proceeding at the coordination sites. Previously we reported paramagnetic derivatives of di-o-quinone (1, Figure 1) with alkali metals [3]. Using the protonated paramagnetic derivatives of the quinone-exTTF-quinone system we succeeded in organization of a symmetric surrounding for both coordination sites of

High performance p-type molecular electron donors for OPV applications via alkylthiophene catenation chromophore extension

• Paul B. Geraghty,
• Calvin Lee,
• Jegadesan Subbiah,
• Wallace W. H. Wong,
• James L. Banal,
• Mohammed A. Jameel,
• Trevor A. Smith and
• David J. Jones

Beilstein J. Org. Chem. 2016, 12, 2298–2314, doi:10.3762/bjoc.12.223

• impacts significantly on the development of highly π–π stacked materials. Shorter chromophore length leads to good stacking in thin films with dominant absorption transitions even in as-cast films for BMR, BTR and BQR. Molecular organization is improved in all films with SVA, except for the longest

Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

• Adrian E. Ion,
• Liliana Cristian,
• Mariana Voicescu,
• Masroor Bangesh,
• Augustin M. Madalan,
• Daniela Bala,
• Constantin Mihailciuc and
• Simona Nica

Beilstein J. Org. Chem. 2016, 12, 1812–1825, doi:10.3762/bjoc.12.171

• exhibit a herringbone arrangement (Figure 2). This organization is sustained by CH–π interactions (H18∙∙∙centroid and H14′∙∙∙C10 contacts are 3.00 and 2.89 Å, respectively; symmetry code: ’ = −0.5 + x, −0.5 + y, 0.5 − z). Instead, the analysis of the packing diagrams in 4b (Figure 3) shows that only the

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

• the World Health Organization (WHO) malaria is a widely distributed illness. About 3.2 billion people remain at risk of malaria and in 2015 214 million cases of malaria and 438 thousands deaths from it have been registered [10]. Compounds with high antimalarial [11][12][13][14][15][16][17][18][19][20

Synthesis and characterization of benzodithiophene and benzotriazole-based polymers for photovoltaic applications

• Desta Gedefaw,
• Marta Tessarolo,
• Margherita Bolognesi,
• Mario Prosa,
• Renee Kroon,
• Wenliu Zhuang,
• Patrik Henriksson,
• Kim Bini,
• Ergang Wang,
• Michele Muccini,
• Mirko Seri and
• Mats R. Andersson

Beilstein J. Org. Chem. 2016, 12, 1629–1637, doi:10.3762/bjoc.12.160

• % and 4.7% were achieved for PTzBDT-1 and PTzBDT-2 based devices, respectively, likely suggesting a different BHJ self-organization as a consequence of the different material properties induced by the alkyl substitution on the aromatic side groups. Results and Discussion Synthesis of the polymers Scheme

• PTzBDT-1 (13 nm). These findings combined with the still different film absorption spectra, suggest a different self-organization of the polymer chains, as supported by additional optical, electrical and morphological investigations of PTzBDT-1 and PTzBDT-2 based blends (vide infra). The HOMO and LUMO

• ], however the subsequent different organization in the solid state might be the main factor responsible for the observed variation of the HOMO and LUMO energy levels, which is in perfect agreement with the different optical properties. Interestingly, the deep HOMO energies of both polymers would result in

Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

• Daniel Wiegmann,
• Stefan Koppermann,
• Marius Wirth,
• Giuliana Niro,
• Kristin Leyerer and
• Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

• Vito Rizzi,
• Sergio Matera,
• Paola Semeraro,
• Paola Fini and
• Pinalysa Cosma

Beilstein J. Org. Chem. 2016, 12, 549–563, doi:10.3762/bjoc.12.54

• through a re-organization of solvating water molecules. Undoubtedly, a combination of these two effects could be considered. At this point, since the obtained UV–vis results are not sufficiently clear to definitely prove the formation of S4TdR/CDs inclusion complexes, in which the pyrimidine ring is

Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen

• Hans Sterckx,
• Johan De Houwer,
• Carl Mensch,
• Wouter Herrebout,
• Kourosch Abbaspour Tehrani and
• Bert U. W. Maes

Beilstein J. Org. Chem. 2016, 12, 144–153, doi:10.3762/bjoc.12.16

• the World Health Organization essential medicines list and despite numerous side effects it remains one of the most effective antimalarial drugs on the market [37][38]. Its classical synthesis (Scheme 2, top) is based on the lithiation of 4-bromo-2,8-bis(trifluoromethyl)quinoline (7a) and quenching

A journey in bioinspired supramolecular chemistry: from molecular tweezers to small molecules that target myotonic dystrophy

• Steven C. Zimmerman

Beilstein J. Org. Chem. 2016, 12, 125–138, doi:10.3762/bjoc.12.14

• personal growth, having learned how to work with a wide range of people and manage a complex organization. The expressions “herding cats” and “drinking from a fire hose” are apropos descriptors as it was more than a full time job and extremely demanding in other ways. Although it was hard to take time away

Bright molecules for sensing, computing and imaging: a tale of two once-troubled cities

• A. Prasanna de Silva

Beilstein J. Org. Chem. 2015, 11, 2774–2784, doi:10.3762/bjoc.11.298

• molecular-mass oligonucleotides [81], both of which involve high levels of organization in space-time. The challenge we faced was to emulate this deep-seated animal behaviour with small molecules with no organization other than to spread them out on paper [82]. Such spreading would create a graphical user

Versatile synthesis and biological evaluation of novel 3’-fluorinated purine nucleosides

• Hang Ren,
• Haoyun An,
• Paul J. Hatala,
• William C. Stevens Jr,
• Jingchao Tao and
• Baicheng He

Beilstein J. Org. Chem. 2015, 11, 2509–2520, doi:10.3762/bjoc.11.272

• largest classes of drugs. Most antimetabolite drugs are nucleoside derivatives that substitute for endogenous nucleosides and prevent DNA and protein replication [1]. Many of the drugs described by the World Health Organization as "essential medicines" are nucleoside derivatives [2] and nearly 20% of all

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

• NaCl) using CD-PEI and Fc8-PAMAM keeping the total concentration constant at [CD] = 100 µM and [Fc] = 50 µM (in Fc and CD moieties from Fc8-PAMAM and CD-PEI, respectively). Acknowledgements This research was supported by the Council for Chemical Sciences of the Netherlands Organization for Scientific

Preparation of Pickering emulsions through interfacial adsorption by soft cyclodextrin nanogels

• Shintaro Kawano,
• Toshiyuki Kida,
• Mitsuru Akashi,
• Hirofumi Sato,
• Motohiro Shizuma and
• Daisuke Ono

Beilstein J. Org. Chem. 2015, 11, 2355–2364, doi:10.3762/bjoc.11.257

• that the adsorption of the CD nanogels at the oil–water interface stabilizes the emulsion. Organization of CD nanogels at the interface To characterize the interfacial structure and to examine the stability of interfacial assembly of the CD nanogels, laser or scanning microscopy observation was

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

• Xiang Sun,
• Guoqiao Lai,
• Zhifang Li,
• Yuwen Ma,
• Xiao Yuan,
• Yongjia Shen and
• Chengyun Wang

Beilstein J. Org. Chem. 2015, 11, 2343–2349, doi:10.3762/bjoc.11.255

• XRD pattern of T1 showed three sharp peaks at 7.4°, 14.9° and 22.1°, which suggested that a lamellar stacking organization was formed [4]. This was not the case for the XRD pattern of T2. In general, intermolecular hydrogen bonding is the main driving force behind self-assembly. Although T2 contains

Synthesis, structure, and mechanical properties of silica nanocomposite polyrotaxane gels

• Kazuaki Kato,
• Daisuke Matsui,
• Koichi Mayumi and
• Kohzo Ito

Beilstein J. Org. Chem. 2015, 11, 2194–2201, doi:10.3762/bjoc.11.238

• following structural analysis. Small-angle X-ray scattering measurement Synchrotron small-angle X-ray scattering (SAXS) experiments were carried out at the beamline 6A of Photon Factory, HighEnergy Accelerator Research Organization, KEK (Tsukuba, Japan). The wavelength λ of the incident X-ray beam was 1.50

• Program of Council for Science, Technology and Innovation (Cabinet Office, Government of Japan). The small-angle X-ray scattering experiments were performed at beamlines BL-6A at the Photon Factory, High Energy Accelerator Research Organization, KEK, with the approval of the Photon Factory Program

Conformational equilibrium in supramolecular chemistry: Dibutyltriuret case

• Karina Mroczyńska,
• Małgorzata Kaczorowska,
• Erkki Kolehmainen,
• Ireneusz Grubecki,
• Marek Pietrzak and
• Borys Ośmiałowski

Beilstein J. Org. Chem. 2015, 11, 2105–2116, doi:10.3762/bjoc.11.227

• observations are in line with computations that are very useful in drawing conclusions. The use of benzoates with regularly changed properties may be the method of choice in analysis of complexes. The pre-organization of molecules used in supramolecular chemistry is, in general, important to this field. On the

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

• realized on this system [59]. By comparison with these results observed for molecular clip 15 [58], it is clear that clips 1–3 exhibit [(TTF)2]+˙ mixed-valence dimer and/or (TTF+˙)2 dimer species but their self-association organization could not be yet demonstrated. The presence of more or less sterically