Hot shape transformation: the role of PSar dehydration in stomatocyte morphogenesis

• Remi Peters,
• Levy A. Charleston,
• Karinan van Eck,
• Teun van Berlo and
• Daniela A. Wilson

Beilstein J. Org. Chem. 2025, 21, 47–54, doi:10.3762/bjoc.21.5

• the PSar-PBLG block copolymers was optimally achieved by dissolving the block copolymers in DMF followed by a solvent-exchange method. Here, Milli-Q water was gradually introduced to form monodisperse polymersomes (Figure 1i, and Supporting Information File 1, Figure S22). Hexafluoroisopropanol (HFIP

• ) emerged as another solvent yielding monodisperse assemblies. HFIP promotes formation of alpha helices in peptides and this property yielded vesicles with different morphologies [30]. The resulting vesicles looked darker compared to those formed in DMF, as observed through TEM (Supporting Information File

Elucidating the glycan-binding specificity and structure of Cucumis melo agglutinin, a new R-type lectin

• Jon Lundstrøm,
• Emilie Gillon,
• Valérie Chazalet,
• Nicole Kerekes,
• Antonio Di Maio,
• Ten Feizi,
• Yan Liu,
• Annabelle Varrot and
• Daniel Bojar

Beilstein J. Org. Chem. 2024, 20, 306–320, doi:10.3762/bjoc.20.31

• necessary for the purification of the CMA1 N-terminal domain (Figure 1d). Expression of the CMA1 C-terminal domain did not yield sufficiently pure and monodisperse protein for further biochemical and structural analyses. Cucumis melo agglutinin binds C2-substituted, beta-linked galactose We then set out to

Inductive heating and flow chemistry – a perfect synergy of emerging enabling technologies

• Conrad Kuhwald,
• Sibel Türkhan and
• Andreas Kirschning

Beilstein J. Org. Chem. 2022, 18, 688–706, doi:10.3762/bjoc.18.70

• conventional heating methods, coupled with shorter cycle and start-up times. Rebrov et al. also suggested that the system can be used during periods of low power consumption to reduce the load on the electrical system. 2.5 Preparation of hydrocarbons (the Fischer–Tropsch process) Monodisperse Fe@FeCo core

Stepwise PEG synthesis featuring deprotection and coupling in one pot

• Logan Mikesell,
• Dhananjani N. A. M. Eriyagama,
• Yipeng Yin,
• Bao-Yuan Lu and
• Shiyue Fang

Beilstein J. Org. Chem. 2021, 17, 2976–2982, doi:10.3762/bjoc.17.207

• synthesis of monodisperse polyethylene glycols (PEGs) and their derivatives usually involves using an acid-labile protecting group such as DMTr and coupling the two PEG moieties together under basic Williamson ether formation conditions. Using this approach, each elongation of PEG is achieved in three steps

• method is expected to significantly lower PEG synthesis cost. Keywords: base-labile; monodisperse; PEG; polyethylene glycol; protecting group; Introduction Polyethylene glycols and derivatives (PEGs) have found wide applications in many areas [1][2][3][4][5][6]. For some applications, polydisperse PEGs

• peptides, proteins and nucleic acids and to evade undesired immune responses, monodisperse PEGs are required or highly desired [12][13]. To meet the needs of monodisperse PEGs, significant efforts have been made to develop stepwise methods for their synthesis [14][15][16][17][18][19][20][21][22][23][24][25

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

• relationships for the mixing process of two liquids are now transferred to free polymer chains in a solvent. For simplicity, a monodisperse polymer is assumed, which, in a first approximation, should behave like a liquid in a solvent. The dissolution of polymers is characterized by strong interactions among the

Oligomeric ricinoleic acid preparation promoted by an efficient and recoverable Brønsted acidic ionic liquid

• Fei You,
• Xing He,
• Song Gao,
• Hong-Ru Li and
• Liang-Nian He

Beilstein J. Org. Chem. 2020, 16, 351–361, doi:10.3762/bjoc.16.34

• oligomerization degree of the product is monodisperse. Actually, the obtained oligomerization degree is the average oligomerization degree. By adopting the index An/Am, the relationship of acid value and oligomerization degree can be constructed. According to the 1H NMR results, the value An/Am increased as the

Nanopatterns of arylene–alkynylene squares on graphite: self-sorting and intercalation

• Tristan J. Keller,
• Joshua Bahr,
• Kristin Gratzfeld,
• Nina Schönfelder,
• Marcin A. Majewski,
• Marcin Stępień,
• Sigurd Höger and
• Stefan-S. Jester

Beilstein J. Org. Chem. 2019, 15, 1848–1855, doi:10.3762/bjoc.15.180

• protective groups [28]. Subsequently, 1a/b were prepared by Pd-catalyzed oxidative cyclodimerization of the respective acetylene-terminated precursors under high-dilution conditions [29][30]. The separation of the crude products by recycling gel permeation chromatography (recGPC) yielded the monodisperse

Mechanochemical synthesis of poly(trimethylene carbonate)s: an example of rate acceleration

• Sora Park and
• Jeung Gon Kim

Beilstein J. Org. Chem. 2019, 15, 963–970, doi:10.3762/bjoc.15.93

• HPLC grade, Fisher) at 40 °C at 1.0 mL/min and calibrated using 14 monodisperse polystyrene standards (Alfa Aesar). The temperature was recorded using a Fluke VT04 Visual IR thermometer. Synthesis of trimethylene carbonate. 1,3-Propanediol (4.72 mL, 0.657 mol) and ethyl chloroformate (12.5 mL, 0.131

A recursive microfluidic platform to explore the emergence of chemical evolution

• David Doran,
• Marc Rodriguez-Garcia,
• Rebecca Turk-MacLeod,
• Geoffrey J. T. Cooper and
• Leroy Cronin

Beilstein J. Org. Chem. 2017, 13, 1702–1709, doi:10.3762/bjoc.13.164

• undertook some experiments to explore osmotic exchange between microdroplets. A mixed but monodisperse population of 50 mM glycylglycine droplets and pure water droplets was used as a model for this process. Due to their greater osmotic pressure, the glycylglycine droplets grew at the expense of the water

• . Monodisperse droplets loaded with complex autocatalytic chemical networks are incubated in the microfluidic device. Those droplets which facilitate the fastest production of high molecular weight polymers from simple precursors exhibit an increase in osmolarity and subsequently grow in size at the expense of

• . Osmotic exchange and coarsening of co-incubating aqueous microdroplets. 50 mM glycylglycine and pure H2O droplets were co-incubated in the same chamber. Upper panel: mixed but monodisperse droplet population at t = 0 min; lower panel: t = 125 min. Real-time, LabVIEWTM tracking of osmosis-driven coarsening

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

• highly monodisperse. Besides sample quality control by using complementary analysis, such as dynamic light scattering, native gel, ultracentrifugation, many BioSAXS beamlines at synchrotrons are nowadays equipped with size exclusion chromatography devices directly connected with the sample cell and 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

• hydrated state. After a BCA control, the fraction of peak 2 containing the larger amount of protein was characterized by cryo-TEM and showed a very monodisperse distribution of particles (Figure 5B) with a diameter in the 5–6 nm range, which might correspond to protein monomers. The peak 1 fraction

• concentration (CMC) of DDM:0.009% or 0.18 mM), no significant population of micelles could be found. These results suggest that the observed particles most likely correspond to a monodisperse preparation of GAT1/GFP. Several studies have demonstrated that GAT1 expresses in an oligomeric formation in the plasma

Novel β-cyclodextrin–eosin conjugates

• Gábor Benkovics,
• Damien Afonso,
• András Darcsi,
• Szabolcs Béni,
• Sabrina Conoci,
• Éva Fenyvesi,
• Lajos Szente,
• Milo Malanga and
• Salvatore Sortino

Beilstein J. Org. Chem. 2017, 13, 543–551, doi:10.3762/bjoc.13.52

• aggregation behavior of eosin B (4)– and eosin Y (2)–β-CD conjugates significantly differ from each other. The size distribution of 2–β-CD shows that the sample is essentially monodisperse with a peak at around 5 nm and this behavior is also observed by transforming the results into volume-related data (see

Assembly of synthetic Aβ miniamyloids on polyol templates

• Sebastian Nils Fischer and
• Armin Geyer

Beilstein J. Org. Chem. 2015, 11, 2646–2653, doi:10.3762/bjoc.11.284

• molecular weights in the region of several kilodalton. Sugars (polyols) were already investigated as templates for peptides [6] and vice versa [7] but both concepts were not yet used for the assembly of monodisperse Aβ miniamyloids. Lehn’s concept of constitutional dynamic chemistry (CDC) [8][9] relies on

• the supramolecular chemistry of Aβ with the concepts of reversible covalent chemistry. The present study shows how oligomers of the Hot=Tap dipeptide serve as templates for the reversible covalent esterification of boronic acids which mediate the assembly of monodisperse Aβ miniamyloids. The modular

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

• Alexander L. Kanibolotsky,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

• separation and is lacking efficient electron mobility. TTF-oligothiophene systems with well-defined structures The monodisperse analogue of polymer 34, bearing two TTF units and capped with dodecyl chains at the terminal positions, was synthesised using chemical coupling protocols, or alternatively via

• . Characterisation of the polymers 34, 35, 37, and 39. Performance of BHJSCs fabricated from the thiophene-TTF hybrid systems. The properties of monodisperse oligothiophene-TTF systems in dichloromethane solution. Acknowledgements PJS thanks the Royal Society for a Wolfson Research Merit Award and ALK thanks the

Impact of multivalent charge presentation on peptide–nanoparticle aggregation

• Daniel Schöne,
• Boris Schade,
• Christoph Böttcher and
• Beate Koksch

Beilstein J. Org. Chem. 2015, 11, 792–803, doi:10.3762/bjoc.11.89

• exchange reaction with mercaptoundecanoic acid [38][39]. The obtained Au/MUA nanoparticles have an average diameter of 5.5 nm, as determined by TEM, and are monodisperse, as confirmed by DLS. An absorption maximum of 525 nm is observed for the Au/MUA nanoparticles in the absence of peptide, even over an

Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin

• Hale Ünal,
• Naile Öztürk and
• Erem Bilensoy

Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22

• monodisperse size distribution of nanocapsules with favourable potential for intracellular drug delivery to tumour cells. Surface charges of anionic and cationic nanocapsules were demonstrated as −21 mV and +18 mV, respectively. The stability of CPT in simulated release media, SGF and SIF were maintained

• wall thickness, is an important parameter in regard to give an idea for the thickness of this nanocapsule shell and for the stability thereby. Hence for further studies 0.1% w/v concentration of polymer was retained. PDI values indicated monodisperse distribution of particles and a higher

Formation of nanoparticles by cooperative inclusion between (S)-camptothecin-modified dextrans and β-cyclodextrin polymers

• Thorbjørn Terndrup Nielsen,
• Catherine Amiel,
• Laurent Duroux,
• Kim Lambertsen Larsen,
• Lars Wagner Städe,
• Reinhard Wimmer and
• Véronique Wintgens

Beilstein J. Org. Chem. 2015, 11, 147–154, doi:10.3762/bjoc.11.14

• polymers. As illustrated in Table 3 the D70GP-CPT2 with a DS of 4.6 mol % forms highly monodisperse nanoparticles when associated with D70HPβ-CD in aqueous media, measured by dynamic light scattering (DLS). The optimum ratio between CPT and β-CD units was found to be 1:1 but even more extreme ratios of 1:4

• and 4:1 led to the formation of nanoparticles. For the 1:1 complexes the concentrations of CPT and β-CD units were 2.25·10−4 M after mixture corresponding to a CPT content of 78 µg/mL. The nanoparticles were stable for more than three days. No monodisperse nanoparticles were formed when associated

Mono- and multilayers of molecular spoked carbazole wheels on graphite

• Stefan-S. Jester,
• A. Vikas Aggarwal,
• Daniel Kalle and
• Sigurd Höger

Beilstein J. Org. Chem. 2014, 10, 2783–2788, doi:10.3762/bjoc.10.295

• ]. They can be viewed as shape-persistent arylene–alkynylene macrocycles in which the intraannular spoke system increases the stiffness (persistence length) of the ring. They are non-collapsible monodisperse cyclooligomers with a fixed and predictable conformation, and their side-chain substitution

Photoswitchable precision glycooligomers and their lectin binding

• Daniela Ponader,
• Sinaida Igde,
• Marko Wehle,
• Katharina Märker,
• Mark Santer,
• David Bléger and
• Laura Hartmann

Beilstein J. Org. Chem. 2014, 10, 1603–1612, doi:10.3762/bjoc.10.166

• building blocks. The obtained glycoligands are monodisperse and present azobenzene moieties as well as sugar ligands at defined positions within the oligomeric backbone and side chains, respectively. We show that the combination of molecular precision together with the photoswitchable properties of the

• functionalities along the backbone, polymer scaffolds make it particularly difficult to correlate their chemical structure with the resulting binding properties. Recently, we introduced a novel synthetic approach towards monodisperse, sequence-defined glycooligomers, so-called precision glycomacromolecules, via

• the combination of solid phase polymer synthesis and tailor-made building blocks [7][8][9]. Through a stepwise assembly of our functional building blocks, we can now control the kind, number, and spacing of sugar ligands along a monodisperse scaffold. Thus, our precision glycomacromolecules allow for

Multivalent scaffolds induce galectin-3 aggregation into nanoparticles

• Candace K. Goodman,
• Mark L. Wolfenden,
• Pratima Nangia-Makker,
• Anna K. Michel,
• Avraham Raz and
• Mary J. Cloninger

Beilstein J. Org. Chem. 2014, 10, 1570–1577, doi:10.3762/bjoc.10.162

• the CRD, the glycodendrimer complex would be expected to have a much smaller diameter than the observed values. Considering the large number of copies of dendrimer and protein that are required to form nanoparticle aggregates of the observed sizes, the aggregates are highly monodisperse. Although it

• formation of large, monodisperse nanoparticle aggregates from galectin-3/glycodendrimer solutions is as follows. The glycodendrimer serves to nucleate the aggregation process through the specific binding of lactose into the carbohydrate binding site on galectin-3. Binding of the carbohydrate into the

• were synthesized and characterized. The presence of complex multivalent interactions between galectin-3 and lactose-functionalized dendrimers is indicated by the observation of large aggregates in DLS and epifluorescence experiments. The large and relatively monodisperse nature of the glycodendrimer

Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks

• Felix Wojcik,
• Sinaida Lel,
• Alexander G. O’Brien,
• Peter H. Seeberger and
• Laura Hartmann

Beilstein J. Org. Chem. 2013, 9, 2395–2403, doi:10.3762/bjoc.9.276

• branched) [18] and biocompatible with a decreased risk of inherent immunogenicity [19]. Recently, we showed that monodisperse, sequence-defined glycooligomers obtained by sequential addition of building blocks on solid support are valuable tools for tuning and understanding carbohydrate–lectin interactions

• reaction conditions for the production of six glycosylated building blocks (Figure 1). These building blocks can then be used for the assembly of monodisperse, sequence-defined glycooligomers via fully automated standard amide coupling. Straightforward variations in the scaffold architecture, number and

• resulting in three monodisperse, sequence-defined glycooligomers with different glycosylation patterns. The building-block approach for the synthesis of glycooligomers thus allows for the control of the ligand positioning as well as the straightforward introduction of defined sequences of different types of

A³-Coupling catalyzed by robust Au nanoparticles covalently bonded to HS-functionalized cellulose nanocrystalline films

• Jian-Lin Huang,
• Derek G. Gray and
• Chao-Jun Li

Beilstein J. Org. Chem. 2013, 9, 1388–1396, doi:10.3762/bjoc.9.155

• Jian-Lin Huang Derek G. Gray Chao-Jun Li Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A0B8, Canada 10.3762/bjoc.9.155 Abstract We decorated HS-functionalized cellulose nanocrystallite (CNC) films with monodisperse Au nanoparticles (AuNPs) to form a

The synthesis of well-defined poly(vinylbenzyl chloride)-grafted nanoparticles via RAFT polymerization

• John Moraes,
• Kohji Ohno,
• Guillaume Gody,
• Thomas Maschmeyer and
• Sébastien Perrier

Beilstein J. Org. Chem. 2013, 9, 1226–1234, doi:10.3762/bjoc.9.139

• (VBC) shell nanoparticles. Optimal conditions for the control of VBC polymerization by RAFT are first established, followed by the use of the “grafting from” method to yield polymeric brushes that form a well-defined shell surrounding the silica core. We obtain particles that are monodisperse in size

• preparing highly monodisperse core–shell nanoparticles, which hold great promise for a range of applications such as drug-delivery vectors or colloidal-crystal self-assemblies [10][11]. RAFT polymerization initiated from preformed inorganic nanoparticles enables the grafting of polymer shells from the

Cyanoethylation of the glucans dextran and pullulan: Substitution pattern and formation of nanostructures and entrapment of magnetic nanoparticles

• Kathrin Fiege,
• Heinrich Lünsdorf,
• Sevil Atarijabarzadeh and
• Petra Mischnick

Beilstein J. Org. Chem. 2012, 8, 551–566, doi:10.3762/bjoc.8.63

• were fixed with strong magnets and washed with distilled water. Monodisperse and regularly shaped iron oxide nanoparticles were obtained as shown by TEM (Figure 9). The iron concentration of the nanoparticle dispersion, as analyzed with inductively coupled plasma optical emission spectroscopy (ICP–OES

Miniemulsion polymerization as a versatile tool for the synthesis of functionalized polymers

• Daniel Crespy and
• Katharina Landfester

Beilstein J. Org. Chem. 2010, 6, 1132–1148, doi:10.3762/bjoc.6.130

• diacrylate to yield, after the transfer to water, stable microgels. Monodisperse latexes could be obtained with the poly(2-hydroxyethyl methacrylate) when water, methanol, ethanol, ethylene glycol, or water/ethanol mixtures were used as the dispersed phase in the presence of cobalt tetrafluoroborate [21

• ]. This approach is particularly interesting to encapsulate large amounts of metal salts. Indeed, up to 22.6 wt % of the cobalt salt compared to the monomer content could be encapsulated. Monodisperse latexes of silver–polymer particles were also obtained upon reduction of silver nitrate in the monomer

• monodisperse nanoparticles with a controlled density of functionalization of the surface. Thus, the influence of the surface functionality nature and density of the nanoparticles on their uptake by different cell lines could be investigated. 2-Aminoethyl methacrylate (0–20 wt %) or acrylic acid were