Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

• Dimitri Fayolle,
• Nathalie Berthet,
• Bastien Doumeche,
• Olivier Renaudet,
• Peter Strazewski and
• Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

• vesicles, alone or in mixture with phospholipids, mimicking bacterial outer membrane vesicles (OMV) with potential antiadhesive properties. Keywords: glycolipids; outer membrane vesicles; synthetic vaccines; Introduction Outer membrane vesicles (OMV) [1], lipid bilayer vesicles released from the outer

• , Figure S4) [1]. This work suggests that mixtures of phospholipids such as POPC and small amounts of bioactive glycolipids should give a controlled bilayer. Such a construct could represent attractive carriers for vaccines once the sugar moiety of the glycolipid is substituted by Tn or Tf antigens [42][43

Synthesis of acylglycerol derivatives by mechanochemistry

• Karen J. Ardila-Fierro,
• Andrij Pich,
• Marc Spehr,
• José G. Hernández and
• Carsten Bolm

Beilstein J. Org. Chem. 2019, 15, 811–817, doi:10.3762/bjoc.15.78

• yields up to 91% (Scheme 4). Particularly interesting was the formation of DAG (18:0/20:4) 5d, an important lipidic backbone present in the biologically relevant phosphatidylinositol 4,5-bisphosphate (PIP2) [22]. In fact, diacylglycerols have proven to play vital roles in regulation of lipid bilayer and

Pd-Catalyzed microwave-assisted synthesis of phosphonated 13α-estrones as potential OATP2B1, 17β-HSD1 and/or STS inhibitors

• Rebeka Jójárt,
• Szabolcs Pécsy,
• György Keglevich,
• Mihály Szécsi,
• Réka Rigó,
• Csilla Özvegy-Laczka,
• Gábor Kecskeméti and
• Erzsébet Mernyák

Beilstein J. Org. Chem. 2018, 14, 2838–2845, doi:10.3762/bjoc.14.262

• phenolic hydroxy function. On the other hand, estrone sulfate is not able to cross the cell membrane passively; therefore, a carrier is needed to mediate its transport across the lipid bilayer. These carriers are certain representatives of the solute carrier superfamily (SLC), including members of 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

• B12 [30]. Indeed, in the crystal structure, 1 maintained the same corrin framework as natural B12 [31]. We combined the hydrophobic B12 derivatives with bilayer vesicles [32][33], a protein [34], organic polymers [35][36][37][38][39][40], and metal organic frameworks (MOFs) [41]. Furthermore, to

• carboxylic ester-migrated product was formed via not a radical, but a cationic intermediate that was generated by the fragmentation to the monoalkylated complex at the anode (Scheme 2). 2-2. Artificial enzyme-mediated reactions A vesicle-type B12 artificial enzyme was constructed by combining bilayer

Synergistic electrodeposition of bilayer films and analysis by Raman spectroscopy

• Saadeldin E. T. Elmasly,
• Luca Guerrini,
• Joseph Cameron,
• Alexander L. Kanibolotsky,
• Neil J. Findlay,
• Karen Faulds and
• Peter J. Skabara

Beilstein J. Org. Chem. 2018, 14, 2186–2189, doi:10.3762/bjoc.14.191

• successfully demonstrated. Moreover, careful control of the electrochemical conditions allows the degree of doping to be effectively altered for one of the polymer layers. Raman spectroscopy confirmed the formation and doped states of the PEDOT/PEDTT bilayer. The electrochemical deposition of a bilayer

• ) raises the possibility of depositing a subsequent layer via solution-processing. Keywords: bilayer; electropolymerisation; PEDOT; PEDTT; Raman; Findings Fabrication of multilayer organic electronic devices has been extensively researched in the past 20 years, resulting in numerous processes and

• two different monomers in a step-wise fashion, a PEDOT/PEDTT bilayer was fabricated. Crucially, this approach provides an insoluble, conductive PEDOT layer, allowing the second PEDTT layer to be deposited on top (and subsequently de-doped), without compromising the initial deposition. Alemán and co

Drug targeting to decrease cardiotoxicity – determination of the cytotoxic effect of GnRH-based conjugates containing doxorubicin, daunorubicin and methotrexate on human cardiomyocytes and endothelial cells

• Livia Polgár,
• Eszter Lajkó,
• Pál Soós,
• Orsolya Láng,
• Marilena Manea,
• Béla Merkely,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 1583–1594, doi:10.3762/bjoc.14.136

• environment, due to the electric insulator character of intact surface membranes composed of the phospholipid bilayer. Application of cytotoxic compounds results in disturbed electrophysical integrity (decreasing value of impedance) of surface membranes as a signal of cell death. While cell physiological

Steric “attraction”: not by dispersion alone

• Ganna Gryn’ova and
• Clémence Corminboeuf

Beilstein J. Org. Chem. 2018, 14, 1482–1490, doi:10.3762/bjoc.14.125

• * hyperconjugative interaction) [17], and a similar argument was used to suggest the possibility of manipulating the band gap of patterned hydrogenated graphene C4H bilayer by an external electric field [27]. Furthermore, Schreiner et al. showed that approx. 10% of the total interaction energy in the tris(3,5-di

• dimers. (A) Dispersion is insufficient to bend the heptacene σ-dimer, but becomes sizable enough in nonacene [2]. (B) Bare hexaphenylethane is not thermodynamically stable, but its all-meta-tert-butyl derivative is [3][4]. (C) Thermodynamically stable (at B97D/6-31G(d,p) level) bilayer of a fully

Design and biological characterization of novel cell-penetrating peptides preferentially targeting cell nuclei and subnuclear regions

• Anja Gronewold,
• Mareike Horn and
• Ines Neundorf

Beilstein J. Org. Chem. 2018, 14, 1378–1388, doi:10.3762/bjoc.14.116

• nuclei; cell-penetrating peptides; nucleoli; subcellular targeting; Introduction Various drugs act on targets that are located within the nucleus, the control center of the eukaryotic cell. A lipid bilayer membrane, which is perforated with nuclear pore complex structures through which the transfer of

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

• ]. Polymersomes comprise an aqueous lumen and hydrophobic membrane. Such hydrophilic and hydrophobic compartments are capable of accommodating hydrophilic (e.g., enzymes) or hydrophobic catalysts (e.g., metal catalysts) in their lumen or bilayer, respectively [28][79]. In an aqueous environment the hydrophobic

• hydrophobic membrane and as a consequence a higher reaction rate. Dergunov et al. reported on the design of a porous polymeric nanoreactor with a lipid bilayer for coupling reactions [87]. These nanocapsules were loaded with palladium catalysts and successfully used in Suzuki, Sonogashira and Heck cross

• 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

Remarkable functions of sn-3 hydroxy and phosphocholine groups in 1,2-diacyl-sn-glycerolipids to induce clockwise (+)-helicity around the 1,2-diacyl moiety: Evidence from conformation analysis by ¹H NMR spectroscopy

• Yoshihiro Nishida,
• Mengfei Yuan,
• Kazuo Fukuda,
• Kaito Fujisawa,
• Hirofumi Dohi and
• Hirotaka Uzawa

Beilstein J. Org. Chem. 2017, 13, 1999–2009, doi:10.3762/bjoc.13.196

• ; deuterium labeling; sn-glycerol; glycerolipids; glycerophospholipids; helicity; Karplus equation; proton NMR spectroscopy; staggered conformers; Introduction Glycerophospholipids, constituting the basic elements of cytoplasm bilayer membranes, are responsible for several cell functions [1][2][3]. These

Chemical systems, chemical contiguity and the emergence of life

• Terrence P. Kee and
• Pierre-Alain Monnard

Beilstein J. Org. Chem. 2017, 13, 1551–1563, doi:10.3762/bjoc.13.155

• for the determination of environmental conditions conducive to the self-assembly of several cellular-like components, such as bilayer membranes [15] and simple energy systems [16], or dynamic processes, such as growth and division [17][18] and potential evolution [19]. However, the experimental set

• nucleic acid oligomers [53][54][55]. The presence of the mineral support is crucial here as it permits the preservation of the amphiphile bilayer structure during drying, thereby promoting the conversion of an “unreactive” organization (free floating vesicles and free monomers) into reactive chemical

• activity, the inserted PAH molecules in turn contributed to stabilizing the aggregates and reducing the bilayer permeability to additional small solutes [74]. That is, feedback interactions between system components significantly increase the probability of coupled functionality, in this case coupling of a

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

• to eight weeks Keeping membrane proteins properly folded outside of a biological membrane is a challenging task. Detergents are needed to refold the applied membrane proteins after their extraction from the natural bilayer environment [35][36][37][38][39][40]. In case of FhuA, so far, refolding has

Grip on complexity in chemical reaction networks

• Albert S. Y. Wong and
• Wilhelm T. S. Huck

Beilstein J. Org. Chem. 2017, 13, 1486–1497, doi:10.3762/bjoc.13.147

• of a bilayer network composed of the mechanical action of a temperature-responsive gel coupled with various exothermic reactions. Reprinted with permission from [34], copyright 2012 Nature Publishing Group. (b) Small dynamic combinatorial library made from dithiol building blocks. Adapted with

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

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

• function associated to this view is that the cell separates between an inside and an outside. In 1935, James Danielli proposed with Hugh Davson that this embodiment was achieved by formation of a bilayer made of amphiphilic lipid molecules [11]. This process is entropy-driven (life belongs to physics, it

• to understand the way proteins interact with membrane lipids, and our knowledge in the domain is still far from complete. There exist many models describing the operation (including ideas about the asymmetry of the bilayer, its local changes and lipid rafts). Work exploring the way proteins are

Correlation of surface pressure and hue of planarizable push–pull chromophores at the air/water interface

• Frederik Neuhaus,
• Fabio Zobi,
• Gerald Brezesinski,
• Marta Dal Molin,
• Stefan Matile and
• Andreas Zumbuehl

Beilstein J. Org. Chem. 2017, 13, 1099–1105, doi:10.3762/bjoc.13.109

• ; membrane pressure; membrane probes; monolayers; Introduction Physical triggers are a major regulator of biological processes. The lateral bilayer membrane pressure, e.g., influences the nucleation [1] and shape changes [2] of lipid domains, it gates mechanosensitive pores [3] and globally organizes cell

• directionally into lipid bilayer membranes. In order to use fluorescent flipper mechanophores for biological measurements, it is crucial to understand the exact relation between surface pressure and their spectroscopic properties. In earlier studies [8], the fluorescence was qualitatively determined in

• . Monolayers at the air/water interface are well known models for biological membranes, avoiding trans-bilayer leaflet correlation effects [11][12][13][14]. Various techniques exist to probe the surface pressure and the lateral organization of the monolayer [14]. Using monolayers of pure flipper probes, we

Aggregation behaviour of a single-chain, phenylene-modified bolalipid and its miscibility with classical phospholipids

• Simon Drescher,
• Vasil M. Garamus,
• Christopher J. Garvey,
• Annette Meister and
• Alfred Blume

Beilstein J. Org. Chem. 2017, 13, 995–1007, doi:10.3762/bjoc.13.99

• flexible nanofibres at 27 °C and further to small elongated micelles at 45 °C. Furthermore, the miscibility of the bolalipid with bilayer-forming phosphatidylcholines (DMPC, DPPC, and DSPC) was investigated by means of DSC, TEM, FTIR, and small angle X-ray scattering (SAXS). We could show that the PC

• -C18pPhC18-PC is partially miscible with saturated phosphatidylcholines; however, closed lipid vesicles with an increased thermal stability were not found. Instead, bilayer fragments and disk-like aggregates are formed. Keywords: aggregation behaviour; bolaamphiphiles; bolalipids; membrane lipids; mixing

• into the bilayer was observed [28]. The reason for this behaviour is that packing problems due to the mismatch between the large space requirement of the PC headgroup of PC-C32-PC and the small cross-sectional area of its single alkyl chain arise. The insertion of a PC-C32-PC molecule in a stretched

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

• maintaining the membrane’s barrier function by increasing the bilayer packing density through condensing the phospholipids. Furthermore, cholesterol is an important player in the dynamic domain structure of the plasma membrane and the formation of lateral lipid domains with relevance to membrane protein

• the presence of 20 mol % of the respective hydroxysterols or cholesterol. The 2H NMR spectra (not shown) exhibited for all samples the typical superposition of Pake doublets with varying quadrupolar splittings as well-known for a lamellar bilayer membrane in the liquid-crystalline phase. From the 2H

• and sphingomyelin being the basis for lipid segregation and, finally, domain formation. What is the physiological consequence of the data presented? We could show that hydroxycholesterols at similarly large membrane concentrations like endogenous cholesterol do not disturb the bilayer structure of the

How and why kinetics, thermodynamics, and chemistry induce the logic of biological evolution

• Addy Pross and
• Robert Pascal

Beilstein J. Org. Chem. 2017, 13, 665–674, doi:10.3762/bjoc.13.66

• of nucleic acid duplexes as well as that of phospholipids to form a bilayer membrane). On the other hand, even though the Second Law must always remain an inescapable constraint, a simple drift towards the equilibrium state is not sufficient to account for the evolutionary changes of life. More

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

• interdigitated bilayer structure. The molecules are oriented side by side such that each hexadecyl alkyl chain is sandwiched between two such chains. The high-intensity peak at 12.75° (d-spacing value of 6.93 Å which is comparable to the width of TPM-G5, 6.99 Å) can be attributed to the distance between adjacent

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

• solution in a round bottom flask. Hydration and extrusion with a Liposofast extruder and membranes with 100 nm pore size yield bilayer vesicles of an approximate size of 100 nm. CDVs were decorated with AdSq by simple addition of the AdSq to the aqueous dispersion of the CDVs. Interestingly, the

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

• postulated that this lipophilic side chain may not be necessary for target inhibition, but for cellular uptake through the lipid bilayer of the cytoplasmic membrane, as an increased lipophilicity is advantageous for this [77][114]. Consequently, several lipophilic derivatives 91a–d were prepared (Figure 9

Smart molecules for imaging, sensing and health (SMITH)

• Bradley D. Smith

Beilstein J. Org. Chem. 2015, 11, 2540–2548, doi:10.3762/bjoc.11.274

• surface of biological membranes [9][10]. Biomembrane science is very challenging because the self-assembled bilayer is a soft and dynamic object that is hard to characterize with spectroscopic methods. To paraphrase a former US president, “we pursue biomembrane science not because it is easy but because

Aggregation behaviour of amphiphilic cyclodextrins: the nucleation stage by atomistic molecular dynamics simulations

• Giuseppina Raffaini,
• Antonino Mazzaglia and
• Fabio Ganazzoli

Beilstein J. Org. Chem. 2015, 11, 2459–2473, doi:10.3762/bjoc.11.267

• for instance the wormlike micelles formed by the cetyltrimethylammonium cations, investigated at various salt concentrations to assess their stability against rupture in smaller spherical micelles [36], or more recently a bilayer of aCDs functionalized through an anthraquinone moiety mimicking a small

• or bilayer, or vesicles and nanospheres at appropriate concentrations. In the recent past, some of these structures have been selected to yield versatile and reliable carriers for drug delivery [3][50], and even for molecular recognition of polymers [51]. In this scenario, the proposed study can open

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

• Mohamed Ramadan El Sayed Aly,
• Hosam Ali Saad and
• Shams Hashim Abdel-Hafez

Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208

• peptides (AMPs) [4] and ceragenins I (Figure 1) [5]. These CSAs selectively bind to the over expressed negatively charged peripheral phospholipids on the internal bacterial cell membranes. Following membrane association, deformation occurs causing bilayer destabilization and cell lysis [6]. According to