Cage-like microstructures via sequential Ugi reactions in aqueous emulsions

• Rita S. Alqubelat,
• Yaroslava A. Menzorova and
• Maxim A. Mironov

Beilstein J. Org. Chem. 2024, 20, 2078–2083, doi:10.3762/bjoc.20.179

• Pickering emulsions. We also recently encountered this problem when we obtained Pickering emulsions stabilized by cellulose particles with an extremely low concentration, which would not have been enough to form a monolayer at the interface [17]. We assumed that in this case, a cage-like structure was

• in favor of the second mechanism. To identify the structure obtained on the surface of the droplets during the formation of the Pickering emulsion, we used fluorescent labels. Aminofluorescein was introduced into the CMC composition with a ratio of 3 mg per 1 g of cellulose using condensation in the

• presence of dicyclohexylcarbodiimide in dimethylformamide. The resulting product was precipitated with acetonitrile, dried, and redissolved in water. Fluorescein-labelled cellulose was used to produce submicron particles according to our previously described method via the Ugi reaction in water (Scheme 1

Polymer degrading marine Microbulbifer bacteria: an un(der)utilized source of chemical and biocatalytic novelty

• Weimao Zhong and
• Vinayak Agarwal

Beilstein J. Org. Chem. 2024, 20, 1635–1651, doi:10.3762/bjoc.20.146

• not only a wide variety of polysaccharides including cellulose, agar, chitin, alginate, and xylan [8][9][10][11], but also plastics [4][12]. Progressing from their isolation and cultivation, natural product discovery from Microbulbifer bacteria is starting to gather steam [6][13][14]. The major

• -linked homopolymer of N-acetyl-β-ᴅ-glucosamine (GlcNAc), the second most abundant biomass on earth after cellulose (Figure 4). Approximately 1011 tons of chitin are produced annually in nature, about 70% of which originate from the ocean. Most of the chitin is recycled by bacteria and fungi as carbon and

Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions

• Martyn Jevric,
• Julian Klepp,
• Johannes Puschnig,
• Oscar Lamb,
• Christopher J. Sumby and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2024, 20, 823–829, doi:10.3762/bjoc.20.74

• ) is produced selectively when cellulose-containing materials, including lignocellulosic biomass, are acidified and pyrolysed [1][2]. Lab scale synthesis of this chiral material can be accomplished in a single step without special glassware [3], while large scale production of the reduction product

Facile access to pyridinium-based bent aromatic amphiphiles: nonionic surface modification of nanocarbons in water

• Lorenzo Catti,
• Shinji Aoyama and
• Michito Yoshizawa

Beilstein J. Org. Chem. 2024, 20, 32–40, doi:10.3762/bjoc.20.5

• solubilized by PA-R in water and subsequently deposited onto a cellulose filter using a simple filtration protocol. Results and Discussion Synthesis of pyridinium-based amphiphiles Synthesis of the pyridinium-based amphiphiles PA-R was achieved in 2–4 steps starting from commercially available 3,5

• sheets with thicknesses of 10–30 nm and widths of 150–300 nm (Figure 6c,d), indicating solubilization of (g-C3N4)m as 20–60 stacks. The encircled g-C3N4-based host–guest composite was subsequently deposited onto a mixed cellulose ester (MCE) filter (50 nm pore-size) using a simple filtration protocol

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen

• Gyula Dargó,
• Dóra Erdélyi,
• Balázs Molnár,
• Péter Kisszékelyi,
• Zsófia Garádi and
• József Kupai

Beilstein J. Org. Chem. 2023, 19, 1811–1824, doi:10.3762/bjoc.19.133

• products) [26]. HPLC: Phenomenex Lux Cellulose-3 column (3 mm, 250 × 4.6 mm), eluent CH3CN/H2O (0.1% formic acid) 40:60, isocratic mode; 0.6 mL min−1; UV detector 222 nm, 30 °C. The retention time for the (S)-enantiomer was 12.3 min, for the (R)-enantiomer 14.7 min. General procedure for recycling of the

• 164.4, 163.9, 135.1, 133.7, 130.7, 129.5, 106.9, 76.1, 49.0, 41.4, 36.8, 36.7, 29.8, 21.8 ppm; HRESI(+)-MS (m/z): [M + Na+] calcd for C17H18ClNO6Na, 390.0720; found, 390.0682; HPLC: Phenomenex Lux Cellulose-3 column (3 mm, 250 × 4.6 mm), eluent CH3CN/H2O (0.2% formic acid) 40:60, isocratic mode; 1 mL

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

• Solomiia Borova and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2023, 19, 217–230, doi:10.3762/bjoc.19.21

• bio-based solvent obtained from cellulose [36][37], commercially known as CyreneTM, and has been introduced as a new "green" solvent marketed specifically as an alternative to solvents such as DMF or NMP, which are particularly interesting for CROP of POx. It is reported that DLG is safe to handle

Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors

• Sedat Ünal,
• Gamze Varan,
• Juan M. Benito,
• Yeşim Aktaş and
• Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

• purchased from Sigma-Aldrich, USA. Chitosan (Protasan UP G-113; MW < 200 kDa) was purchased from Novamatrix, Norway. Dialysis cellulose tubing membrane for in vitro release studies (average flat width 25 mm, MWCO: 14,000 Da) was obtained from Sigma-Aldrich, USA. Cell culture studies were performed on CT26

Inline purification in continuous flow synthesis – opportunities and challenges

• Jorge García-Lacuna and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182

• dissolve the magnesium salts, and the organic mixture was the appropriate solvent for the next step. Recently, a regenerated cellulose membrane to purify micelles via inline dialysis was reported by Junkers and co-workers [63]. This semicontinuous closed-loop setup can remove the organic solvent (THF) to a

Oxa-Michael-initiated cascade reactions of levoglucosenone

• Julian Klepp,
• Thomas Bousfield,
• Hugh Cummins,
• Sarah V. A.-M. Legendre,
• Jason E. Camp and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2022, 18, 1457–1462, doi:10.3762/bjoc.18.151

• chemistry; levoglucosenone; oxa-Michael reaction; Introduction (−)-Levoglucosenone (1) is formed from the acid-catalyzed pyrolysis of cellulose along with minor amounts of furfural and 5-methylfurfural [1][2][3]. It has emerged as a promising starting material for enantioselective synthesis from materials

Polymer and small molecule mechanochemistry: closer than ever

• José G. Hernández

Beilstein J. Org. Chem. 2022, 18, 1225–1235, doi:10.3762/bjoc.18.128

• -free ball milling has enabled to surpass the insolubility and recalcitrant reactivity of cellulose [36][37], chitin [38][39], and lignin (Figure 2) [40][41]. In addition to allowing solvent-free reactions, mechanical forces generated inside ball mills can depolymerize biomass through cleavage pathways

• cellulose and chitin and approximation to the structure of lignin. Tensile forces by ball milling change the conformation of a chitin model compound. This deformation facilitates the subsequent cleavage of glycosidic bonds to produce oxocarbenium ion intermediates for hydrolysis [45]. (a) Representation of

A trustworthy mechanochemical route to isocyanides

• Francesco Basoccu,
• Federico Cuccu,
• Federico Casti,
• Rita Mocci,
• Claudia Fattuoni and
• Andrea Porcheddu

Beilstein J. Org. Chem. 2022, 18, 732–737, doi:10.3762/bjoc.18.73

• hydrolyse the p-tosyl chloride excess. Our approach for the removal of the unreacted p-tosyl chloride was demonstrated to be the most feasible and eco-friendly compared with the reported techniques, which imply the use of cellulose with a large excess of pyridine [40] and the need for flash chromatography

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

• major components, lignin and cellulose, were pyrolyzed by RF heating at high temperatures ranging from 500 °C to 700 °C. The authors found that higher temperature resulted in higher gas yield and lower liquid yield. The results could be relevant to the forestry and paper industries, which produce large

Terpenoids from Glechoma hederacea var. longituba and their biological activities

• Dong Hyun Kim,
• Song Lim Ham,
• Zahra Khan,
• Sun Yeou Kim,
• Sang Un Choi,
• Chung Sub Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2022, 18, 555–566, doi:10.3762/bjoc.18.58

• was performed using a Gilson 321 pump with a Shodex Refractive Index Detector, an INNO column C18 5 μm column (250 × 10 mm), and a Lux 5 μm Cellulose-1 column (250 × 4.6 mm). Silica gel 60 (Merck, 70–230 mesh and 230–400 mesh), RP-C18 silica gel (Merck, 230–400 mesh), Sephadex LH-20 (Parmacia Co

A resorcin[4]arene hexameric capsule as a supramolecular catalyst in elimination and isomerization reactions

• Tommaso Lorenzetto,
• Fabrizio Fabris and
• Alessandro Scarso

Beilstein J. Org. Chem. 2022, 18, 337–349, doi:10.3762/bjoc.18.38

• leading to the promotion of the elimination reaction. β-Pinene isomerization β-Pinene is a bicyclic monoterpene bearing an exocyclic C=C double bond that can be recovered in large quantities from the production processes of cellulose from the wood of conifers. β-Pinene is in equilibrium with the more

Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks

• Jolita Bruzgulienė,
• Greta Račkauskienė,
• Aurimas Bieliauskas,
• Vaida Milišiūnaitė,
• Miglė Dagilienė,
• Gita Matulevičiūtė,
• Vytas Martynaitis,
• Sonata Krikštolaitytė,
• Frank A. Sløk and
• Algirdas Šačkus

Beilstein J. Org. Chem. 2022, 18, 102–109, doi:10.3762/bjoc.18.11

• correlations of compound 4a. Stacked chromatogram view of pairs of enantiomers with area, %: (R)-4b, ee 100% (tR = 10.1 min) and (S)-4c, ee 100% (tR = 9.6 min); conditions: CHIRAL ART Cellulose-SB (100 × 4.6 mm I.D., S-3 µm, chiral selector cellulose tris(3,5-dimethylphenylcarbamate), YMC); mobile phase: ACN

Unsaturated fatty acids and a prenylated tryptophan derivative from a rare actinomycete of the genus Couchioplanes

• Shun Saito,
• Kanji Indo,
• Naoya Oku,
• Hisayuki Komaki,
• Masashi Kawasaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2939–2949, doi:10.3762/bjoc.17.203

• between the diastereomer pairs. The enantiomer ratio of 4 was estimated to be S/R = 56:44 or near by chiral phase HPLC analysis of 4' on a cellulose tribenzoate-coated silica gel column (Figure 4). Thus, 4 was concluded to be an enantiomeric mixture of (2E,4E)-7-hydroxy-2,4-dimethyl-2,4-octadienoic acid

• . (S)-MPA ester of 7R enantiomer 4'd: 1H NMR data was identical to those of 4'a. Chiral HPLC analysis A 0.2 μL-portion of 4', dissolved in iPrOH, was injected into a cellulose tribenzoate-coated silica gel column (CHIRALCEL OB-H, 4.6 mm × 250 mm, Daicel Co.) eluted with n-hexane/iPrOH (4:1) at 0.5 mL

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

• Luke O. Jones,
• Leah Williams,
• Tasmin Boam,
• Martin Kalmet,
• Chidubem Oguike and
• Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

• [11][33][39]. Thermoresponsive cryogels comprising oligoethylene glycol have also been reported with dual shape memory behaviour [40]. Natural polymers such as cellulose derivatives, chitosan, gelatin, and dextran exhibit temperature-responsive properties and have been used in cryogels. 3.2. pH

• prior to printing [68]. They demonstrated the ability to control pore sizes by altering the temperature of the frozen bed used and the temperature of the dispensing probe. Successfully 3D-printed sodium carboxymethyl cellulose (CMC)-based cryogels were subsequently coated with collagen to promote cell

• significant increase in the total number of cells, and more particularly infiltration by DCs. The works done by Bauleth-Ramos et al. [82] and Bencherif et al. [27] suggest that the cryogels may help to combat against cancers. Injectable composite cryogels based on GelMA, and cellulose nanocrystals (CNC) or

Post-functionalization of drug-loaded nanoparticles prepared by polymerization-induced self-assembly (PISA) with mitochondria targeting ligands

• Janina-Miriam Noy,
• Fan Chen and
• Martina Stenzel

Beilstein J. Org. Chem. 2021, 17, 2302–2314, doi:10.3762/bjoc.17.148

• solution was stirred for 45 min and the pH was adjusted to 8.3 and the solution was stirred for 3 days at room temperature. The particles were purified by dialysis in Milli-Q water with frequent solvent change (regenerated cellulose membranes, MW cut-off 6000–8000 g mol−1) and analysed via DLS experiments

• 8.2 and the reaction was left to stir at room temperature for 3 days. The polymer was purified by dialysis in Milli-Q water with frequent solvent change (regenerated cellulose membranes, MW cut-off 6000–8000 g mol−1) and the product was then lyophilized and analysed using NMR spectroscopy. 1H NMR (300

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• methodologies or post-extraction modifications are not discussed. Review Glucose-based polysaccharides Cellulose Cellulose is a polymer consisting of glucose units connected by β(1–4) glycosidic bonds. It is mainly found in two allomorphs – Cellulose I (natural) and Cellulose II (synthetic) – that differ in the

• orientation of the individual chains and in the number of hydrogen bonds in the crystalline structures [42][43]. In Cellulose I, the chains are oriented parallel, whereas in Cellulose II antiparallel. Natural cellulose is produced by cellulose synthases [44][45][46]. As the chain gets elongated, microfibrils

• and produce long and uniform polysaccharides. Solvent systems like DMAc/LiCl or quaternary ammonium electrolytes are able to dissolve cellulose and could overcome the precipitation issues during synthesis [55][56]; however, these systems are not always compatible with reaction conditions [57]. The

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane

• David Weinzierl and
• Mario Waser

Beilstein J. Org. Chem. 2021, 17, 800–804, doi:10.3762/bjoc.17.68

• Cellulose-SB stationary phase. Optical rotations were recorded on a Schmidt + Haensch Polarimeter Model UniPol L1000 at 589 nm. All chemicals were purchased from commercial suppliers and used without further purification unless otherwise stated. rac-2 was prepared from 1 according to a previously published

• ), 35.4 (1C, -CH2), 34.9 (1C, -CH2), 34.0 (1C, -CH2), 32.2 (1C, -CH2); HRMS (ESI) m/z: calcd for [C16H16O + H]+, 225.1274; found, 225.1280, HPLC: YMC Chiral ART Cellulose-SB, n-hexane/iPrOH 3:1, 1 mL/min, 10 °C; tR = 6.4 min [Sp; minor], 7.2 min [Rp; major]. (Sp)-3a: Analytical data match those reported

• (1C, -CH2), 35.0 (1C, -CH2), 34.4 (2C, -CH, -CH2), 31.8 (1C, -CH2), 19.4 (1C, -CH3), 19.1 (1C, -CH3); HRMS (ESI) m/z: calcd for [C20H22O2 + NH4]+, 312.1958; found, 312.1958, HPLC: YMC Chiral ART Cellulose-SB, n-hexane/iPrOH 3:1, 1 mL/min, 10 °C; tR = 7.3 min [Rp; minor], 8.4 min [Sp; major]. Overview

Valorisation of plastic waste via metal-catalysed depolymerisation

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

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

• valorisation of naturally-occurring polymeric waste, i.e., lignocellulosic biomass [97][98], particularly lignin [99][100] and cellulose [101], to monomers or added-value platform molecules [102][103]. Here the main drawbacks concern safety hazards, supply, transport and storage costs of hydrogen. Catalytic

Identification of volatiles from six marine Celeribacter strains

• Anuj Kumar Chhalodia,
• Jan Rinkel,
• Dorota Konvalinkova,
• Jörn Petersen and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 420–430, doi:10.3762/bjoc.17.38

• using a YMC ChiralART Cellulose-SC column. This yielded 70% of (Z)-42 and 6% of (E)-42, and their analysis by GC–MS showed retention indices of I = 1177 for (E)-42 and I = 1200 for (Z)-42, revealing that the compound in the headspace extracts of C. marinus DSM 100036T and C. manganoxidans DSM 27541T was

• 2.1L (deuterium lamp, 190–700 nm) and a YMC ChiralART Cellulose-SC column (5 μm; 250 × 20 mm) with a guard column of the same type (30 × 20 mm). The elution was performed with hexane/propanol 60:40 (isocratic) at a flow rate of 10 mL min−1 (36 bar). The UV–vis absorption was monitored at 275 nm

Progress in the total synthesis of inthomycins

• Bidyut Kumar Senapati

Beilstein J. Org. Chem. 2021, 17, 58–82, doi:10.3762/bjoc.17.7

• Omura’s group in 1995 [3]. Inthomycin A ((+)-1) displays moderate antifungal activity against cellulose-containing Phytophthora parasitica and Phytophthora capsici [4]. Inthomycins were reported to possess many interesting biological properties, which include the specific inhibition of the cellular

Easy access to a carbohydrate-based template for stimuli-responsive surfactants

• Thomas Holmstrøm,
• Daniel Raydan and
• Christian Marcus Pedersen

Beilstein J. Org. Chem. 2020, 16, 2788–2794, doi:10.3762/bjoc.16.229

• and lipophilic groups at a late stage of the synthesis (Figure 1a). The synthesis is centered around the cheap and commercially available levoglucosan, a glucose derivative that can be produced directly from cellulose [19]. This building block seemed ideal for the synthesis of a stimuli-responsive