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

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

• ]. Among the variety of amphipathic or hydrophobic small molecules that exhibit a lipid structure, diacylglycerols (DAGs) are important due to their signaling functions in cells (DAG signaling) [22][23][24]. Structurally, DAGs are glycerolipids containing two fatty acids esterified to the alcohol glycerol

• fatty acids (e.g., chain length, degree of unsaturation, double bond position or stereochemistry), the access to pure DAGs and TAGs from natural sources by extraction is cumbersome. Alternatively, protected DAGs 5 can be chemically synthesized starting from glycerol [26] or glycidol [27], but either

Thermophilic phosphoribosyltransferases Thermus thermophilus HB27 in nucleotide synthesis

• Ilja V. Fateev,
• Ekaterina V. Sinitsina,
• Aiguzel U. Bikanasova,
• Maria A. Kostromina,
• Elena S. Tuzova,
• Larisa V. Esipova,
• Tatiana I. Muravyova,
• Alexei L. Kayushin,
• Irina D. Konstantinova and
• Roman S. Esipov

Beilstein J. Org. Chem. 2018, 14, 3098–3105, doi:10.3762/bjoc.14.289

• -4-one 5'-monophosphate (Allop-MP) using TthНPRT with yields of 37% and 32%, respectively. Using of hypoxanthine and adenine transferases in multi-enzyme cascades significantly extends the spectrum of synthetic purine nucleotides. Experimental Tris-buffer, acetic acid, sodium chloride, glycerol

• 8.0 (4 CV, flow rate 2 mL/min). Pooled fractions were concentrated by a polysulfonic membrane PBGC 10 kDa (Millipore, USA). The resulting solution was applied to a column with HiLoad 16/60 Superdex 75pg (GE Healthcare, USA), equilibrated by 20 mM Tris-HCl, 50 mM NaCl, 0.04% NaN3, and 10% glycerol, pH

• , contained the target enzyme, were pooled and concentrated on polysulphonic membrane PBGC 10 kDa. The resulting solution was applied to column with HiLoad 16/60 Superdex 200, equilibrated by 20 mM Tris-HCl, 50 mM NaCl, 0.04% NaN3, and 5% glycerol, pH 8.0. Fractions, contained the target enzyme with purity

An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes

• Hashem Sharghi,
• Pezhman Shiri and
• Mahdi Aberi

Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253

• -methyl-1H-imidazolium chloride (66) ILs were used as excellent catalysts and the reaction medium for microwave synthesis of quinoline derivatives 65 from substituted anilines 15 and glycerol (64, Scheme 11). Some advantages of these catalytic systems include: elimination of oxidizing agents, ease of

• isolation of products, very short reaction times (only 10 s), and better yields. The use of glycerol as a starting material is another important advantage because it is the main byproduct in the biodiesel industry and the application of renewable feedstocks for the preparation of suitable chemicals and

• peaks at 4.10–4.32 and 5.31–5.35 ppm for the glycerol scaffold and olefinic protons, respectively. Biodiesel formation was approved through the invisibility of the protons of the glycerol scaffold and appearance of a single peak at 3.63 ppm related to the methyl esters of fatty acids. The catalyst

Non-native autoinducer analogs capable of modulating the SdiA quorum sensing receptor in Salmonella enterica serovar Typhimurium

• Matthew J. Styles and
• Helen E. Blackwell

Beilstein J. Org. Chem. 2018, 14, 2651–2664, doi:10.3762/bjoc.14.243

• profiles in SdiA was also of interest. Lastly, we included compound 23, 1-octanoyl-rac-glycerol (Figure 1B), in our assays as X-ray crystallographic studies revealed it was present in the AHL binding site of SdiA (from EHEC) when purified in the absence of AHL (i.e., a complex that originally was thought

• head group to a phenyl or cyclohexane was not well tolerated; however, cyclopentane, thiolactones, and the alternative stereochemistry, D-lactone were generally tolerated. Interestingly, 1-octanoyl-rac-glycerol (23) showed no agonism in this reporter assay, suggesting it does not act as an AHL signal

• ], Nguyen et al. observed that two residues in the ligand-binding pocket, Phe59 and Leu77, were moved inward toward the alkyl tail of 2, effectively closing the binding pocket relative to the “apo”-SdiA structure (bound to 1-octanoyl-rac-glycerol (23)). In Salmonella SdiA, these side chains are switched

Spectroelectrochemical studies on the effect of cations in the alkaline glycerol oxidation reaction over carbon nanotube-supported Pd nanoparticles

• Dennis Hiltrop,
• Steffen Cychy,
• Karina Elumeeva,
• Wolfgang Schuhmann and
• Martin Muhler

Beilstein J. Org. Chem. 2018, 14, 1428–1435, doi:10.3762/bjoc.14.120

• , 44780 Bochum, Germany 10.3762/bjoc.14.120 Abstract The effects of the alkali cations Na+ and K+ were investigated in the alkaline electrochemical oxidation of glycerol over Pd nanoparticles (NPs) deposited on functionalized carbon nanotubes (CNTs). The electrocatalytic activity was assessed by cyclic

• voltammetry revealing a lower overpotential of glycerol oxidation for nitrogen-functionalized Pd/NCNTs compared with oxygen-functionalized Pd/OCNTs. Whereas significantly lower current densities were observed for Pd/OCNT in NaOH than in KOH in agreement with stronger non-covalent interactions on the Pd

• oxidation. Keywords: cation effect; electrocatalysis; glycerol oxidation; in situ electrochemistry/IR spectroscopy; Introduction The conversion of biomass to biofuels is a promising process for carbon-neutral energy conversion [1]. First-generation biofuels such as bioethanol or biodiesel are produced

Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor

• Morten M. C. H. van Schie,
• Tiago Pedroso de Almeida,
• Gabriele Laudadio,
• Florian Tieves,
• Elena Fernández-Fueyo,
• Timothy Noël,
• Isabel W. C. E. Arends and
• Frank Hollmann

Beilstein J. Org. Chem. 2018, 14, 697–703, doi:10.3762/bjoc.14.58

• refolding. The PeAAOx was solubilized using 150 µg mL−1 protein in 20 mM Tris/HCl buffer, pH 9.0, containing 2.5 mM GSSG, 1 mM DTT, 0.02 mM FAD, 34% glycerol and 0.6 M urea at 4 °C for 80 h. After the incubation for PeAAOx activation/refolding, the refolding mixture was concentrated to 100 mL and the buffer

Preparation of trinucleotide phosphoramidites as synthons for the synthesis of gene libraries

• Ruth Suchsland,
• Bettina Appel and
• Sabine Müller

Beilstein J. Org. Chem. 2018, 14, 397–406, doi:10.3762/bjoc.14.28

• released by a transesterification mechanism [35]. The 3'-start nucleoside is bound to one of the primary hydroxy groups of CPG-linked glycerol via an H-phosphonate linkage (Figure 5B). The removal of the TBDMS group from the remaining primary alcohol of glycerol induces the spontaneous cleavage of the H

Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays

• Marco Russo,
• Daniele La Corte,
• Annalisa Pisciotta,
• Serena Riela,
• Rosa Alduina and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271

• [68]. For EMSA experiments, constant amounts (200 ng) of pDNA were incubated for 30 minutes at room temperature in a final volume of 20 µL of binding buffer 1× (12.5 mM Tris HCl pH 7.5, 10% glycerol, 62.5 mM KCl, 0.75 mM DTT), using different N/P ratios (average number of nitrogen atoms on the

• cells were collected by centrifugation, resuspended in a 70 mM CaCl2 solution and incubated on ice for 1 hour. Then, the cells were collected by centrifugation, treated with freezing solution (70 mM CaCl2/10% glycerol (w/v)), aliquoted and finally stored at −80 °C. Transformation of calcium competent E

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

• of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba 305-8565, Japan 10.3762/bjoc.13.196 Abstract Cell-membrane glycerolipids exhibit a common structural backbone of asymmetric 1,2-diacyl-sn-glycerol bearing polar head groups in the sn-3 position. In this study, the possible

• ; 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

• chiral biomolecules have an asymmetric sn-glycerol backbone. Although sn-glycerol is symmetric, an sn-3 phosphate group makes it chiral with an (R)-configuration at the sn-2 position [4]. Such molecular chirality is crucial to not only their biological activities but also for their metaphysical

Sustainable synthesis of 3-substituted phthalides via a catalytic one-pot cascade strategy from 2-formylbenzoic acid with β-keto acids in glycerol

• Lina Jia and
• Fuzhong Han

Beilstein J. Org. Chem. 2017, 13, 1425–1429, doi:10.3762/bjoc.13.139

• phthalides in good to excellent yields. Conclusion: A concise and efficient synthesis strategy of 3-substituted phthalides from 2-formylbenzoic acid and β-keto acids via a catalytic one-pot cascade reaction in glycerol has been accomplished. Keywords: β-keto acid; decarboxylation; glycerol; one-pot cascade

• straightforward method for the preparation of several biologically active compounds of medicinal and agrochemical interest [23][24][25][26][27][28][29][30]. Notably, the decarboxylative reaction of β-keto acids provides a traceless means of activation with CO2 as the only byproduct. On the other hand, glycerol

• transformations have been accomplished using glycerol as a solvent [32][33][34][35][36][37][38][39][40]. Therefore, as part of our ongoing research interest in exploring novel and sustainable transformations of β-keto acids [41][42], we envisioned that the direct utilization of β-keto acids as nucleophilic

An improved preparation of phorbol from croton oil

• Alberto Pagani,
• Simone Gaeta,
• Andrei I. Savchenko,
• Craig M. Williams and
• Giovanni Appendino

Beilstein J. Org. Chem. 2017, 13, 1361–1367, doi:10.3762/bjoc.13.133

• of phorbol from the transesterification reaction mixture, a viscous oil for the presence of glycerol, that requires extended periods (four weeks according to ref. [6]). Furthermore, the unstable ethanol solvate has to be transformed into a more stable hydrate by recrystallization from hot water, a

• glycerol obtained after hydrolysis of the oil and washing with organic solvents must be evaporated with care, maintaining an acidic pH to minimize epimerization to 4α-phorbol [19]. Next, the recovery of phorbol from the resulting ca 10% solution of phorboids in glycerol is difficult under both normal- and

• reverse-phase silica gel chromatography, that fail to separate phorbol from 4α-4-deoxyphorbol (3a) because of their similar chromatographic behavior and of the presence of glycerol. As a result, the week-long crystallization from water was still necessary [19], a process that, tediousness aside, we found

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

• ‘trigger-freeze” approach consists in the use of various soaking times for the crystal with substrate sugars in presence of H2O or glycerol (“trigger step”) followed by the freezing step ranging from a few minutes to several hours. The use of a “freeze-trigger” approach solves the synchronization issue but

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

• atomic composition of matter: N for nitrogen, Fe, for iron, C for carbon). Thus a chemical molecule is information-rich. sn-Glycerol-3-phosphate can be described, including an outline of its three-dimensional configuration, by a limited alphabet of symbols (e.g., the Simplified Molecular Input Line Entry

• Specification (SMILES) code table [8]), C([C@H](COP(=O)(O)O)O)O, while its mirror symmetry sn-glycerol-1-phosphate is summarised as C([C@@H](COP(=O)(O)O)O)O. That this coding is sufficient (if associated to a concrete machine) is visible in Figure 1, where I used these codes with an algorithm to generate the

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

• behaviour; nanofibres; self-assembly; Introduction Bolalipids are amphiphilic molecules consisting of two hydrophilic headgroups attached to both ends of a long hydrocarbon spacer [1]. The hydrophobic spacer is composed of either a single alkyl chain or two chains connected via a glycerol moiety. These

• in the chemical structure of those archaeal membrane lipids: the alkyl chains are connected via ether linkages in the inverse sn-2,3 configuration to the glycerol, the alkyl chains sometimes contain a varying number of cyclopentane rings or several methyl branches [2][3], and some of the archaeal

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• ]. It was found that irradiation times of 14 min could be employed to afford CDs from glycerol, glycol, glucose or sucrose. The source of the inorganic ion was important too, as increasing the valency of either the anion or cation would lead to a greater ability to dehydrate the carbon precursor. An

• improved materials with high QYs. Non-glucose monosaccharide-based fluorescent carbon dots In addition to glucose, different monosaccharides and polyols have also been utilised as carbon sources for the synthesis of FCD, although this approach is less common. The ability of glycerol to undergo dehydration

• and polymerisation in the presence of amino groups makes it a cheap and suitable candidate as a molecular precursor for CD synthesis. To that end, Liu et al. demonstrated in 2011 that the microwave-assisted pyrolysis of glycerol in the presence of TTDDA afforded blue-emissive CDs with a QY of 12

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

• a rotary shaker (200 rpm) at 30 °C for 4 days. Then, the seed culture (3 mL) was transferred into 500 mL K-1 flasks each containing 100 mL of the A-3M production medium consisting of soluble starch 2.0%, glycerol 2.0%, glucose 0.5%, Pharmamedia (Traders Protein) 1.5%, yeast extract 0.3%, and Diaion

Poly(ethylene glycol)s as grinding additives in the mechanochemical preparation of highly functionalized 3,5-disubstituted hydantoins

• Andrea Mascitti,
• Massimiliano Lupacchini,
• Ruben Guerra,
• Ilya Taydakov,
• Lucia Tonucci,
• Nicola d’Alessandro,
• Frederic Lamaty,
• Jean Martinez and
• Evelina Colacino

Beilstein J. Org. Chem. 2017, 13, 19–25, doi:10.3762/bjoc.13.3

• the polymer chain length. After selecting the optimal polymer amount (450 mg mmol−1), the study was carried on by increasing (Table 1, entry 11) or reducing (Table 1, entries 12 and 13) the polymer chain length, changing the end terminal substituents (Table 1, entries 6 vs 3), and adding glycerol

• reactants. Decreased and comparable yields were also observed by reducing the PEG chain length (Table 1, entry 13) and by using glycerol. It is also worth noting here that not only viscosity, but any modification of the physical state of the system impacted the outcome of the reaction. Indeed, HO-PEG-600-OH

• (0.119 cSt) led to comparable yields when replaced by a more viscous liquid like glycerol (1.12 cSt) (Table 1, entry 14), an eco-friendly solvent still not investigated for liquid-assisted grinding procedures. In fact such a compound is becoming a green source of several building blocks since glycerol is

Biochemical and structural characterisation of the second oxidative crosslinking step during the biosynthesis of the glycopeptide antibiotic A47934

• Veronika Ulrich,
• Clara Brieke and
• Max J. Cryle

Beilstein J. Org. Chem. 2016, 12, 2849–2864, doi:10.3762/bjoc.12.284

• -function relationship of StaF, we attempted to structurally characterise the protein. We were able to determine the crystal structure of StaF to a resolution of 2.1 Å and 2.2 Å using different cryo-protectant solutions (ethylene glycol and glycerol) and by solving the phase problem through molecular

• (≈150 µm length) had formed. The crystals were passed through a cryoprotectant solution (0.1 M phosphate/citrate buffer (pH 4.2), 1.2 M Na2PO4, 0.3 M K2HPO4 and either 25% (v/v) glycerol, or 25% (v/v) ethylene glycol) and then flash cooled in liquid nitrogen for data collection. Two native data sets

• building and refinement were performed using the programs COOT [54] and REFMAC [55] with TLS refinement [56] following a simulated annealing performed in CNS [57][58]. During several rounds of refinement with REFMAC and manual rebuilding, ethylene glycol or glycerol and solvent molecules were included in

Formose reaction controlled by boronic acid compounds

• Toru Imai,
• Tomohiro Michitaka and
• Akihito Hashidzume

Beilstein J. Org. Chem. 2016, 12, 2668–2672, doi:10.3762/bjoc.12.263

• six-carbon sugar alcohols (ethylene glycol, glycerol, erythritol, D-arabinitol, and D-mannitol, respectively) (Figure 2a). In Figure 2b–d, the signals at ca. 5 min may be due to impurities, e.g., inorganic salts. As can be seen in Figure 2b, the HPLC chart for the formose reaction in the absence of

A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus

• Jan Rinkel,
• Patrick Rabe,
• Laura zur Horst and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2016, 12, 2317–2324, doi:10.3762/bjoc.12.225

• , 0.5 M imidazole, 1 mM MgCl2, pH 7.0) and used directly for incubations with 5 mg of (1R)- and (1S)-(1-2H)GPP, solved in incubation buffer (50 mM Tris/HCl, 10 mM MgCl2, 20% v/v glycerol, pH 8.2) to reach a final substrate concentration of 0.2 mg/mL. The enzyme reaction was incubated for 2 h at 28 h