Volatile emission and biosynthesis in endophytic fungi colonizing black poplar leaves

• Christin Walther,
• Pamela Baumann,
• Katrin Luck,
• Beate Rothe,
• Peter H. W. Biedermann,
• Jonathan Gershenzon,
• Tobias G. Köllner and
• Sybille B. Unsicker

Beilstein J. Org. Chem. 2021, 17, 1698–1711, doi:10.3762/bjoc.17.118

• : initiation and activation of polymerase (95 °C/5 min); followed by 35 cycles of denaturation (95 °C/30 s), annealing (65 °C/30 s) and elongation (72 °C/90 s) and a single, final elongation step (72 °C/10 min). For gel electrophoresis, 4 µL PCR product was mixed with one drop loading dye (0.3 mL 30% glycerol

• by a 4 × 20 s treatment with a sonicator (Bandelin UW2070, Berlin, Germany) in chilled extraction buffer (10 mM Tris-HCl, pH 7.5, 1 mM dithiothreitol, 10% (v/v) glycerol). Cell fragments were removed by centrifugation at 14,000g and the supernatant was further processed via an Illustra NAP-5 gravity

Fritsch–Buttenberg–Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes

• Tsutomu Kimura,
• Koto Sekiguchi,
• Akane Ando and
• Aki Imafuji

Beilstein J. Org. Chem. 2021, 17, 1352–1359, doi:10.3762/bjoc.17.94

• JNM-LA 500, Bruker AVANCE DPX 300, and Bruker AVANCE DPX 400 spectrometers. Mass spectrometry (MS) experiments were conducted at 70 eV by direct injection with a HITACHI M-80B mass spectrometer. Fast atom bombardment (FAB) mass spectra were obtained with a mixture of m-nitrobenzyl alcohol and glycerol

A new glance at the chemosphere of macroalgal–bacterial interactions: In situ profiling of metabolites in symbiosis by mass spectrometry

• Marine Vallet,
• Filip Kaftan,
• Veit Grabe,
• Fatemeh Ghaderiardakani,
• Simona Fenizia,
• Aleš Svatoš,
• Georg Pohnert and
• Thomas Wichard

Beilstein J. Org. Chem. 2021, 17, 1313–1322, doi:10.3762/bjoc.17.91

• . MS6 and Roseovarius sp. MS2 forming a tripartite community [3][7][8] (see also Figure 1a and the Graphical Abstract). In turn, Roseovarius sp. benefits from the released photosynthate glycerol as a carbon source [9]. Axenic Ulva germ cells (i.e. gametes) develop into a callus-like phenotype composed

• zwitterion dimethylsulphoniopropionate (DMSP), resulting in biofilm formation on the algal surrounding [9]. The bacterium subsequently uses the provided glycerol for growth and transforms DMSP into methanethiol and dimethyl sulphide [9]. The metabolic activities of marine bacteria and algae can be surveyed

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

Nitroalkene reduction in deep eutectic solvents promoted by BH₃NH₃

• Chiara Faverio,
• Monica Fiorenza Boselli,
• Patricia Camarero Gonzalez,
• Alessandra Puglisi and
• Maurizio Benaglia

Beilstein J. Org. Chem. 2021, 17, 1041–1047, doi:10.3762/bjoc.17.83

• product was isolated in 27% yield. For sake of comparison, the reaction was also performed in water, where a negligible amount of the product was detected, and in glycerol, which proved to be a good reaction medium (41% yield) [17]. In order to further speed up the reaction and suppress the byproducts

• formation [18], the reaction was performed at 60 °C for 18 h on a 0,1 M substrate concentration (entries 6–9, Table 1). Under those conditions, the product was isolated after chromatographic purification in a higher yield; in DES B, 41% yield was reached, while in glycerol, the reaction gave 61% yield

• (entries 6 and 8, Table 1). Therefore, DES mixture B (ChCl/gly 1:2) and glycerol were selected as reaction media of choice to further investigate the reduction of nitroalkenes mediated by ammonia borane. Both solvent systems represent promising alternatives, green solvents for organic reactions; glycerol

Synthesis of 10-O-aryl-substituted berberine derivatives by Chan–Evans–Lam coupling and investigation of their DNA-binding properties

• Peter Jonas Wickhorst,
• Mathilda Blachnik,
• Denisa Lagumdzija and
• Heiko Ihmels

Beilstein J. Org. Chem. 2021, 17, 991–1000, doi:10.3762/bjoc.17.81

• low fluorescence quantum yields are caused by conformational changes in the excited state, the fluorescence was recorded in media with different viscosity, namely in glycerol at different temperatures (Figure 2, Figure S2, Supporting Information File 1). It was observed that the derivatives 5a–e have

• significantly higher, but still relatively low emission quantum yields in glycerol at room temperature (Φfl = 0.009–0.031, 20 °C, η = 1412 cP) [41], whereas the emission intensity decreased with increasing temperature (Φfl = 0.001–0.002, 80 °C, η = 32 cP) [41]. Such a behavior usually indicates a radiationless

• deactivation of the excited state by conformational changes, e.g., torsional relaxation [42][43]. Since the fluorescence quantum yield of the parent berberine (1a) does not correlate well with the viscosity of the medium [40], it was concluded that the weak light-up effect in glycerol is mainly caused by the

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

• Christopher Liczner,
• Kieran Duke,
• Gabrielle Juneau,
• Martin Egli and
• Christopher J. Wilds

Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76

• (R) or (S) starting material, respectively. These simple nucleic acid building blocks were first synthesized in 1971 by Ueda et al. [96]. The group was able to synthesize adenine, cytosine, and uracil GNA analogues by reacting these bases with glycerol α-chlorohydrin or glycidol. The following year

• glycerol α-chlorohydrin, the ratio of I/II was 1:4 with II being the preferred isomer but when using glycidol, this ratio shifted to 3:1 in the favor of the desired isomer [96][97]. From there on, the use of glycidol for the preparation of GNA analogues became the gold standard. The first GNA polymers were

Kinetics of enzyme-catalysed desymmetrisation of prochiral substrates: product enantiomeric excess is not always constant

• Peter J. Halling

Beilstein J. Org. Chem. 2021, 17, 873–884, doi:10.3762/bjoc.17.73

• diol ester hydrolysis, Keq will probably depend significantly on the positions of the hydroxy groups with respect to each other. A value around 40 M was found for glycerol dioctanoate [35]. Effect of eeDP and k−4 · Keq/k4 on the product ee at high conversion for “ping-pong, first” kinetics. S0 = 0.2 M

Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition

• Maryna O. Mazur,
• Oleksii S. Zhelavskyi,
• Eugene M. Zviagin,
• Svitlana V. Shishkina,
• Vladimir I. Musatov,
• Maksim A. Kolosov,
• Elena H. Shvets,
• Anna Yu. Andryushchenko and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2021, 17, 678–687, doi:10.3762/bjoc.17.57

• reaction time (Table 1, entries 11–24) as variables. Reactions in such solvents as ethanol and glycerol resulted in almost no conversion. The treatment in water led to a mixture of the product with the starting material where low conversion can be explained by solubility issues. To overcome this, the

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

Synthetic strategies of phosphonodepsipeptides

• Jiaxi Xu

Beilstein J. Org. Chem. 2021, 17, 461–484, doi:10.3762/bjoc.17.41

• library of carboxylic acids 72 in the presence of coupling reagents (Scheme 11) [27]. Alternatively, the 1,3-protected glycerol 73 was first converted into various 2,3-protected glycerols 74, which were further transformed to methyl 2-alkoxy-3-hydroxypropanoates 75. Following a similar strategy as above

Regioselective chemoenzymatic syntheses of ferulate conjugates as chromogenic substrates for feruloyl esterases

• Olga Gherbovet,
• Fernando Ferreira,
• Apolline Clément,
• Mélanie Ragon,
• Julien Durand,
• Sophie Bozonnet,
• Michael J. O'Donohue and
• Régis Fauré

Beilstein J. Org. Chem. 2021, 17, 325–333, doi:10.3762/bjoc.17.30

• glycerol (pKa = 13.61) or ʟ-arabinose (pKa = 11.31) [41], meaning that it is a poor leaving group. Moreover, our observations regarding the linker stability are consistent with the known stability of the ester linkages under basic conditions. The usefulness of 4NTC–linker–Fe (12) for the characterization

Ultrasound-assisted Strecker synthesis of novel 2-(hetero)aryl-2-(arylamino)acetonitrile derivatives

• Emese Gal,
• Luiza Gaina,
• Hermina Petkes,
• Alexandra Pop,
• Castelia Cristea,
• Gabriel Barta,
• Dan Cristian Vodnar and
• Luminiţa Silaghi-Dumitrescu

Beilstein J. Org. Chem. 2020, 16, 2929–2936, doi:10.3762/bjoc.16.242

• using “green” solvents, for example, low vapor pressure solvents such as ionic liquids [3], low volatile solvents such as glycerol, ethylene glycol and its oligomers, or nontoxic water solvent, as well as in heterogeneous media under solvent-free conditions [4]. Other advantages induced by sonication

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

• Paola Vitale,
• Luciana Cicco,
• Ilaria Cellamare,
• Filippo M. Perna,
• Antonio Salomone and
• Vito Capriati

Beilstein J. Org. Chem. 2020, 16, 1915–1923, doi:10.3762/bjoc.16.158

• imidazole (32–98% yield) and pyrimidine derivatives (45–88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/urea (1:2 mol/mol)] as environmentally benign and non-innocent reaction media, by modulating the temperature (25 or 80

• symmetrical pyrazines, we observed that phenacyl bromide (1a, 1.5 mmol) could be almost quantitatively converted into phenacyl azide (2a, 97% yield), within 4 h, when treated with NaN3 (1.65 mmol) as the azide source in a choline chloride (ChCl)/glycerol (Gly) (1:2 mol/mol) eutectic mixture at room

• electron-donating groups like MeO. Studies to expand even more the scope and the selectivity of such DES-promoted heterocyclization reactions and to elucidate their mechanism are in progress. Experimental General methods Deep eutectic solvents [choline chloride (ChCl)/glycerol (Gly) (1:2 mol/mol); choline

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway

• Esra Demir,
• Ozlem Sari,
• Yasin Çetinkaya,
• Ufuk Atmaca,
• Safiye Sağ Erdem and
• Murat Çelik

Beilstein J. Org. Chem. 2020, 16, 1805–1819, doi:10.3762/bjoc.16.148

• polymerization of the compounds containing cyclic carbonates such as methyl 4,6-O-benzylidene-2,3-O-carbonyl-α-ᴅ-glucopyranoside (MBCG) (5) [19][20] and glycerol carbonate (6) [21] were also reported (Scheme 1). Therefore, numerous synthetic approaches have been developed to date for the preparation of

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

• high-throughput reaction screening, both of which are progressive areas of chemical research [69][70][71][72][73]. 2 Heterogeneous photocatalysts Probably the first report of HPC was published by Renz in 1921, who observed the partial reduction of titania (TiO2) in the presence of glycerol when

Anthelmintic drug discovery: target identification, screening methods and the role of open science

• Frederick A. Partridge,
• Ruth Forman,
• Carole J. R. Bataille,
• Graham M. Wynne,
• Marina Nick,
• Angela J. Russell,
• Kathryn J. Else and
• David B. Sattelle

Beilstein J. Org. Chem. 2020, 16, 1203–1224, doi:10.3762/bjoc.16.105

• sequenced [85]. C. elegans occurs as hermaphrodites and males and its capacity for hermaphroditic reproduction (selfing) facilitates the long-term maintenance of genetic strains. The capacity to freeze and store strains in glycerol adds to its utility. The transparency of the worm facilitates studies on the

A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium

• Shun Saito,
• Kota Atsumi,
• Tao Zhou,
• Keisuke Fukaya,
• Daisuke Urabe,
• Naoya Oku,
• Md. Rokon Ul Karim,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1100–1110, doi:10.3762/bjoc.16.97

• consisting of glucose 0.5%, glycerol 2%, soluble starch 2%, Pharmamedia (Traders Protein) 1.5%, dry yeast (Kamaishi Hamayuri Yeast, Nihon Tensai Seito Co., Ltd.) 0.3%. The pH of the medium was adjusted to 7.0 before sterilization. The inoculated flasks were placed on a rotary shaker TB98 (Takasaki Scientific

Two new aromatic polyketides from a sponge-derived Fusarium

• Mada Triandala Sibero,
• Tao Zhou,
• Keisuke Fukaya,
• Daisuke Urabe,
• Ocky K. Karna Radjasa,
• Agus Sabdono,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2941–2947, doi:10.3762/bjoc.15.289

• %, MgSO4·7H2O 0.05%, and CaCO3 0.3% (pH 7.0). The flasks were shaken at 30 °C for 4 days on a rotary shaker (200 rpm). The seed culture (3 mL) was transferred into 500 mL K-1 flasks each containing 100 mL of A3M production medium (pH 7.0) consisting of 2.0% soluble starch, 0.5% glucose, 2.0% glycerol, 0.3

Unexpected one-pot formation of the 1H-6a,8a-epiminotricyclopenta[a,c,e][8]annulene system from cyclopentanone, ammonia and dimethyl fumarate. Synthesis of highly strained polycyclic nitroxide and EPR study

• Sergey A. Dobrynin,
• Igor A. Kirilyuk,
• Yuri V. Gatilov,
• Andrey A. Kuzhelev,
• Olesya A. Krumkacheva,
• Matvey V. Fedin,
• Michael K. Bowman and
• Elena G. Bagryanskaya

Beilstein J. Org. Chem. 2019, 15, 2664–2670, doi:10.3762/bjoc.15.259

• labels for measurements at room temperature [10]. In this paper we examined the properties of this new nitroxide, in particular, the electron spin relaxation at different temperatures in water/glycerol solution. Results and Discussion Synthesis Polycyclic amine A mixture cyclopentanone, dimethyl fumarate

• molecules along the a-axis. EPR measurements Figure 4 demonstrates the X-band CW EPR spectra of nitroxide 6 in water/glycerol solution at 180 K and at room temperature with simulations (red) using the parameters listed in the caption. The electron spin relaxation of nitroxides with different bulky

• substituents has been studied in water/glycerol solutions at low temperatures in numerous papers [9][14][15][16]. Previously, we have investigated the electron spin relaxation of a series of nitroxides with different bulky substituents in water solution and in trehalose [10]. Because 6 is a new class of a

Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

• Heather J. Lacey,
• Cameron L. M. Gilchrist,
• Andrew Crombie,
• John A. Kalaitzis,
• Daniel Vuong,
• Peter J. Rutledge,
• Peter Turner,
• John I. Pitt,
• Ernest Lacey,
• Yit-Heng Chooi and
• Andrew M. Piggott

Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256

• of glycerol casein (AC), Czapek-Dox (CZ), malt extract (MA) and yeast extract (YS) media, and the grains, pearl barley (PB), cracked wheat (BL), jasmine rice (JR) and basmati rice (BS) were prepared in accordance with recipes provided in Table S1 in Supporting Information File 1. The culture was

Reaction of oxiranes with cyclodextrins under high-energy ball-milling conditions

• László Jicsinszky,
• Federica Calsolaro,
• Katia Martina,
• Fabio Bucciol,
• Maela Manzoli and
• Giancarlo Cravotto

Beilstein J. Org. Chem. 2019, 15, 1448–1459, doi:10.3762/bjoc.15.145

• the higher reaction temperature. As the epichlorohydrin is in a large molar excess at the beginning of the reaction, its partial hydrolysis can result in the presence of glycerol moieties. Although it is true that the hydrolysis can be impeded somewhat by adding the reagents to the reaction mixture in

Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response

• Yu-Ying Wang,
• Yong Kong,
• Zhe Zheng,
• Wen-Chao Geng,
• Zi-Yi Zhao,
• Hongwei Sun and
• Dong-Sheng Guo

Beilstein J. Org. Chem. 2019, 15, 1394–1406, doi:10.3762/bjoc.15.139

• , respectively, by plotting the maximum emission wavenumbers of 2,6-TNS/1,8-ANS in a set of solvents as a function of solvent polarity ET(30) (Figure 1e and 1f). ET(30) values for the involved solvents (water, methanol, ethanol, propanol, butanol, glycerol and ethylene glycol) and the maximum emission

A chemically contiguous hapten approach for a heroin–fentanyl vaccine

• Yoshihiro Natori,
• Candy S. Hwang,
• Lucy Lin,
• Lauren C. Smith,
• Bin Zhou and
• Kim D. Janda

Beilstein J. Org. Chem. 2019, 15, 1020–1031, doi:10.3762/bjoc.15.100

• coating the protein’s surface (i.e., 10.0 copies). However, increasing the conjugation to a 1 mg scale caused the protein to precipitate immediately upon addition of HF-1 in 9:1 DMF/H2O solution, eliminating the possibility of conjugation. To mitigate this precipitation problem, glycerol was added to the

• soluble KLH or BSA solution (Figures S2–S7, Supporting Information File 1). Concerned by the possibility that the alcohols on glycerol would outcompete amidation, we tested several concentrations of glycerol in the range of 10–50% (w/w). Based on MALDI–TOF data and as expected, the conjugation with the

• least amount of glycerol had the highest number of hapten copies (i.e., 11.1 copies). Addition of 50% w/w glycerol reduced the hapten density by one-half (i.e., 5.2 copies). After dialysis, the solutions remained translucent, but the protein conjugates did not crash out of the solution. As a reference

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

• % inhibition of WGA-HRP binding to PAA-GlcNAc coated plates was determined (IC50). Docking experiments: WGA structure was obtained from the Protein Data Bank (2UVO) and unbound ligands (water, GlcNAc, glycerol and pyroglutamic acid) were removed. PDB files for compounds 4C2, 4C4, 5C2, 5C4, 7C2, 7C4, 8C2 and