Formaldehyde surrogates in multicomponent reactions

• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Bernhard Westermann

Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45

• carbon atom, due to the readiness for losing a water molecule. Formaldehyde is commonly used in its polymeric form (paraformaldehyde) or in a 37% aqueous solution (formalin). The exceptional solubility of formaldehyde in water or biobased solvents, such as ethanol and glycerol, enhances the feasibility

The scent gland composition of the Mangshan pit viper, Protobothrops mangshanensis

• Jonas Holste,
• Paul Weldon,
• Donald Boyer and
• Stefan Schulz

Beilstein J. Org. Chem. 2024, 20, 2644–2654, doi:10.3762/bjoc.20.222

• components, carboxylic acids, alcohols, glycerol ethers, amides, and volatile compounds such as phenol, benzaldehyde, or indole were present (Figure 1 and Table 1). While some of these compounds were easily identified, a group of diketopiperazines (DKPs) and a series of unknown putative carboxylic acids (A–F

Cell-free protein synthesis with technical additives – expanding the parameter space of in vitro gene expression

• Tabea Bartsch,
• Stephan Lütz and
• Katrin Rosenthal

Beilstein J. Org. Chem. 2024, 20, 2242–2253, doi:10.3762/bjoc.20.192

• /ethylene glycol (EG), and choline chloride/glycerol) were chosen as additives to vary the viscosity, ion concentration, amount of macromolecules, and osmolarity in CFPS. The calculated values for the properties of the CFPS system with polymers and DES added at different concentrations are shown in Table 1

• . Although the viscosities of pure DES are relatively high (choline chloride/urea 1:2: 1200 mPa·s [28], choline chloride/glycerol 1:2: 300 mPa·s [28], betaine/ethylene glycol 1:3: 65 mPa·s [29]), the effect on viscosity when adding 2–10% to the CFPS system is almost negligible. The concentration of inorganic

• system increases to 1329 mOsm. Next to choline chloride/urea and choline chloride/glycerol, betaine/ethylene glycol (EG) was tested as it is considered to be an environmentally friendly natural deep eutectic solvent (NADES) [30] and is widely used with proteins [31]. As it does not consist of any ions

Factors influencing the performance of organocatalysts immobilised on solid supports: A review

• Zsuzsanna Fehér,
• Dóra Richter,
• Gyula Dargó and
• József Kupai

Beilstein J. Org. Chem. 2024, 20, 2129–2142, doi:10.3762/bjoc.20.183

• was studied and compared in the esterification of methanol or glycerol with oleic acid (1). It was observed that substrate conversion and product yield also depended on the particle morphology. Rope-type propylsulfonic SBA-15 mesoporous silica gel showed the highest catalytic activity in both studied

Computational toolbox for the analysis of protein–glycan interactions

• Ferran Nieto-Fabregat,
• Maria Pia Lenza,
• Angela Marseglia,
• Cristina Di Carluccio,
• Antonio Molinaro,
• Alba Silipo and
• Roberta Marchetti

Beilstein J. Org. Chem. 2024, 20, 2084–2107, doi:10.3762/bjoc.20.180

Discovery of antimicrobial peptides clostrisin and cellulosin from Clostridium: insights into their structures, co-localized biosynthetic gene clusters, and antibiotic activity

• Moisés Alejandro Alejo Hernandez,
• Katia Pamela Villavicencio Sánchez,
• Rosendo Sánchez Morales,
• Karla Georgina Hernández-Magro Gil,
• David Silverio Moreno-Gutiérrez,
• Eddie Guillermo Sanchez-Rueda,
• Yanet Teresa-Cruz,
• Brian Choi,
• Armando Hernández Garcia,
• Alba Romero-Rodríguez,
• Oscar Juárez,
• Siseth Martínez-Caballero,
• Mario Figueroa and
• Corina-Diana Ceapă

Beilstein J. Org. Chem. 2024, 20, 1800–1816, doi:10.3762/bjoc.20.159

• 0.8. Cultures were incubated for 14 h, at 200 rpm, at 18 °C. Subsequently, cells were centrifuged at 10,000 rpm for 30 min at 4 °C. The resulting cell pellets were resuspended in 20 mL of LanA starting buffer (20 mM Tris pH 7.5, 500 mM KCl, 10% glycerol) and lysed by sonication (4.0 seconds on, 10

• KCl, 10% glycerol, 0.5 mM imidazole), followed by 10 column volumes of LanA wash buffer 2 (20 mM Tris pH 7.5, 500 mM KCl, 10% glycerol, 30 mM imidazole). Finally, the elution was performed with 3 column volumes of LanA elution buffer (20 mM Tris pH 7.5, 500 mM KCl, 10% glycerol, 750 mM imidazole

Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations

• Alexander V. Tsygankov,
• Vladyslav O. Vereshchak,
• Tetiana O. Savluk,
• Serhiy M. Desenko,
• Valeriia V. Ananieva,
• Oleksandr V. Buravov,
• Yana I. Sakhno,
• Svitlana V. Shishkina and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2024, 20, 1773–1784, doi:10.3762/bjoc.20.156

• experience of the authors [27][32], we tried to apply the described hydrolysis conditions (5 equiv HCl in MeOH) to our products (compounds 5). As a model reaction, we heated a mixture of Ugi bisamide 5d and an aqueous solution of HCl in methanol (glycerol bath, 80 °C) in a hermetically sealed vial with

Sustainable tandem acylation/Diels–Alder reaction toward versatile tricyclic epoxyisoindole-7-carboxylic acids in renewable green solvents

• Ayhan Yıldırım

Beilstein J. Org. Chem. 2024, 20, 1308–1319, doi:10.3762/bjoc.20.114

• importance in intramolecular Diels–Alder reactions, the effects of solvents such as glycerol, polyethylene glycol, organic carbonates, deep eutectic solvents, supercritical CO2 and H2O have recently been extensively studied [65][66][67]. Recently, attention has also been drawn to photoinduced oxidative [4

HPW-Catalyzed environmentally benign approach to imidazo[1,2-a]pyridines

• Luan A. Martinho and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2024, 20, 628–637, doi:10.3762/bjoc.20.55

• -Aminopyridine (1a), 4-nitrobenzaldehyde (2a), and tert-butyl isocyanide (3a) were chosen as model substrates and different conditions were screened (Table 1). Glycerol, a green and sustainable solvent, was tried first, but unfortunately, the expected intense orange solid product 4a was obtained in low yields

A myo-inositol dehydrogenase involved in aminocyclitol biosynthesis of hygromycin A

• Michael O. Akintubosun and
• Melanie A. Higgins

Beilstein J. Org. Chem. 2024, 20, 589–596, doi:10.3762/bjoc.20.51

• mL−1 tetracycline and grown at 200 rpm and 37 °C overnight. One liter of autoinduction media (20 g L−1 tryptone, 10 g L−1 yeast extract, 50 mM NH4Cl, 2 mM MgSO4, 0.5% glycerol, 17 mM KH2PO4, 72 mM K2HPO4, 0.05% glucose, and 0.2% lactose) supplemented with 10 μg mL−1 ampicillin and 1.5 μg mL−1

• coefficient 33,460 M−1 cm−1 and 38,350 M−1 cm−1 for Hyg17 and BsIDH, respectively [29]. Protein was flash frozen in liquid nitrogen at 100 μM in 20 mM Tris pH 8, 50 mM NaCl, and 10% glycerol and stored at −80 °C for biochemical assays. Enzyme assays Generally, 100 μL reactions contained 10 mM inositol

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

• Jens Frackenpohl,
• David M. Barber,
• Guido Bojack,
• Birgit Bollenbach-Wahl,
• Ralf Braun,
• Rahel Getachew,
• Sabine Hohmann,
• Kwang-Yoon Ko,
• Karoline Kurowski,
• Bernd Laber,
• Rebecca L. Mattison,
• Thomas Müller,
• Anna M. Reingruber,
• Dirk Schmutzler and
• Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

• . Active fractions were pooled together, and the buffer was exchanged into 25 mM potassium phosphate buffer pH 7.3 containing 10% glycerol with PD10 columns (GE Healthcare). Aliquots of the protein solution were frozen in liquid nitrogen and stored at −80 °C. LpFAT A fluorescence polarization assay

A new analog of dihydroxybenzoic acid from Saccharopolyspora sp. KR21-0001

• Rattiya Janthanom,
• Yuta Kikuchi,
• Hiroki Kanto,
• Tomoyasu Hirose,
• Arisu Tahara,
• Takahiro Ishii,
• Arinthip Thamchaipenet and
• Yuki Inahashi

Beilstein J. Org. Chem. 2024, 20, 497–503, doi:10.3762/bjoc.20.44

• ; pH 7.0) as the starter and incubated at 180 rpm in a rotary shaker at 27 °C for 4 days. The 1% portion of the starter was transferred into 20 L of production medium (2% glycerol, 2% soybean meal, and 0.3% NaCl) in a jar fermenter and further incubated at 150 rpm, 27 °C, 0.5 VVM (volume per volume per

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

• well as Lewis acids, such as FeCl3 [23][24], RuCl3·3H2O [25], AgNO3 [26], glycerol and [Fe(III)-(salen)]Cl [27], Fe(DS)3·nH2O [28], Sc(OTf)3 [29], B(C6F5)3 or PhSiCl3 [30] and Cp2TiCl2 [31]. However, most of these reactions face some serious drawbacks, such as the requirement of large quantities of the

Preparing a liquid crystalline dispersion of carbon nanotubes with high aspect ratio

• Keiko Kojima,
• Nodoka Kosugi,
• Hirokuni Jintoku,
• Kazufumi Kobashi and
• Toshiya Okazaki

Beilstein J. Org. Chem. 2024, 20, 52–58, doi:10.3762/bjoc.20.7

• with previous studies [22][23]. Initially, 100 mg of DWCNT powder was pre-dispersed in 100 mL of Wako glycerol with a stirrer (ASONE, HPS-100PD) rotating at 500 rpm for 18 hours. During the stirring, the DWCNTs were defibrated by the shear stress of the high-viscosity glycerol [36]. After suspension in

• 200 mL of water, the DWCNT-glycerol mixture was filtered through a 1.0 μm pore size polytetrafluoroethylene (PTFE) membrane (Merck, Omnipore 47mm). To ensure complete removal of glycerol from the DWCNTs, we repeated the washing process until 2 L of water had passed through the membrane, resulting in

Identification of the p-coumaric acid biosynthetic gene cluster in Kutzneria albida: insights into the diazotization-dependent deamination pathway

• Seiji Kawai,
• Akito Yamada,
• Yohei Katsuyama and
• Yasuo Ohnishi

Beilstein J. Org. Chem. 2024, 20, 1–11, doi:10.3762/bjoc.20.1

• -cmaA3 into E. coli BL21(DE3). The obtained strain was cultured in 1 L of Terrific broth (24 g/L yeast extract, 12 g/L tryptone, 0.8% glycerol, 0.94% K2HPO4, and 0.22% KH2PO4) with ampicillin and chloramphenicol (if necessary for sfp expression) and incubated with shaking (150 rpm) at 37 °C until the

• were harvested by centrifugation and suspended in lysis buffer (20 mM HEPES-NaOH, 10% glycerol, and 200 mM NaCl2; pH 8.0). The cells were disrupted by sonication on ice, and cell debris was removed by centrifugation. The recombinant protein was purified using His60 Ni Superflow Resin (TaKaRa Bio Inc

• [13] were used in the current experiment. In vitro analysis of CmaA1, CmaA3, AvaA1, and AvaA3 A reaction mixture (50 µL) containing 4 µM CmaA1 or AvaA1, 40 µM CmaA3 or AvaA3, 2.5 mM 3,4-AHBA, 1 mM ATP, 5 mM MgCl2, 20 mM HEPES-NaOH (pH 8.0), 10% glycerol, and 200 mM NaCl was prepared and incubated at

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

• Stéphanie Hesse

Beilstein J. Org. Chem. 2023, 19, 1537–1544, doi:10.3762/bjoc.19.110

• characterized; a pH value of 10.07 was measured at 30 °C by Shah et al. [16] and a viscosity of 750 cP at 25 °C was reported by Mjalli et al. [17] (Table 1). It remains today one of the most used DES and studies on it are still conducted [14]. ChCl/glycerol (ChCl/Gly; 1:2) is another classical DES with a

• synthesis of NaDES plays a major role in the resulting viscosity [20]. For example, ʟ-proline/glycerol (Pro/Gly; 1:2) was found to have a pH value of 7.25 and a viscosity of 5064 cP [20]. In 2018, Molnar et al. reported the antioxidant activity of a series of rhodanine derivatives synthesized by a

• Knoevenagel condensation is well documented [21]. Moreover, the low cost and high availability of ʟ-proline has attracted attention to ʟ-proline-based DES. Especially, in 2022, Detsi [20] has synthesized and characterized three ʟ-proline-based NaDES: proline/oxalic acid (1:1), proline/glycerol (1:2), and

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

• living organisms including humans that feature an ether bond linkage at the sn-1 position of the glycerol. This class of lipids features singular structural roles and biological functions. Alkyl ether lipids and alkenyl ether lipids (also identified as plasmalogens) correspond to the two sub-classes of

• compounds. Keywords: amphiphiles; edelfosine; GAEL; glycerol lipids; glycolipids; ohmline; plasmalogen; Introduction Ether lipids (ELs) are natural compounds that feature a glycerol unit linked with an ether function to an alkyl (alkyl acyl ether lipid) or alkenyl (plasmalogen) lipid chain. For the

• alkenyl compounds, the vinyl ether function is characterized by a (Z)-configuration as shown in Figure 1. In addition, an acyl group is present on the secondary alcohol of the glycerol. This acyl group is constituted by a saturated or unsaturated lipid chain or, in the case of platelet-activating factor

Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea

• Winnie Chemutai Sum,
• Sherif S. Ebada,
• Didsanutda Gonkhom,
• Cony Decock,
• Rémy Bertrand Teponno,
• Josphat Clement Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84

• was weighed out into 10 × 500 mL Erlenmeyer flasks, each containing 90 mL of deionized H2O and autoclaved. In addition, 20 × 200 mL Erlenmeyer flasks containing cotton seed flour (Q6/2) liquid-state fermentation media were prepared as follows: media components (ᴅ-glucose 2.5 g/L, glycerol 10 g/L

Nostochopcerol, a new antibacterial monoacylglycerol from the edible cyanobacterium Nostochopsis lobatus

• Naoya Oku,
• Saki Hayashi,
• Yuji Yamaguchi,
• Hiroyuki Takenaka and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2023, 19, 133–138, doi:10.3762/bjoc.19.13

• , Japan 10.3762/bjoc.19.13 Abstract A new antibacterial 3-monoacyl-sn-glycerol, nostochopcerol (1), was isolated from a cultured algal mass of the edible cyanobacterium Nostochopsis lobatus MAC0804NAN. The structure of compound 1 was established by the analysis of NMR and MS data while its chirality was

• commercially available, methyl linoleate, having the same degree of unsaturation with a longer chain length by two carbons, was used as a source of the acyl chain. Linoleic acid, obtained by saponification of methyl linoleate, was condensed either with (R)- or (S)-solketal (isopropylidene glycerol) by Steglich

• esterification. The resulting ester 2a or 2b was purified by reversed-phase HPLC and deprotected by a short treatment with 80% aqueous acetic acid at 58–59 °C to give 1-linoleoyl-sn-glycerol (3a) or 3-linoleoyl-sn-glycerol (3b), respectively (Scheme 1). Similarly, to our experience during the isolation of

A Streptomyces P450 enzyme dimerizes isoflavones from plants

• Run-Zhou Liu,
• Shanchong Chen and
• Lihan Zhang

Beilstein J. Org. Chem. 2022, 18, 1107–1115, doi:10.3762/bjoc.18.113

• NaCl, 1 mM TCEP, 10% glycerol, pH 7.5) and stored at −80 °C for further use. The P450 partner proteins, FdR and Fdx, were constructed according to the reported method [40]. For in vitro biochemical assays, the reaction mixture (50 µL) contained 0.4 mM substrate, 3 µM P450 enzyme, 5 µM FdR, 5 µM Fdx, 1

Automated grindstone chemistry: a simple and facile way for PEG-assisted stoichiometry-controlled halogenation of phenols and anilines using N-halosuccinimides

• Dharmendra Das,
• Akhil A. Bhosle,
• Amrita Chatterjee and
• Mainak Banerjee

Beilstein J. Org. Chem. 2022, 18, 999–1008, doi:10.3762/bjoc.18.100

• relatively inferior results than EtOH (Table 1, entry 3). The use of ethylene glycol and glycerol as the grinding matrix showed improved yields with the monobromo product 2a formed in 81% and 85% yield, respectively within 10 min (Table 1, entries 4 and 5). Next, liquid polyethylene glycol, PEG-400 was

Efficient production of clerodane and ent-kaurane diterpenes through truncated artificial pathways in Escherichia coli

• Fang-Ru Li,
• Xiaoxu Lin,
• Qian Yang,
• Ning-Hua Tan and
• Liao-Bin Dong

Beilstein J. Org. Chem. 2022, 18, 881–888, doi:10.3762/bjoc.18.89

• -kaurene production were created. Next, DL10003–10006 were fermented in Lysogeny broth (LB) medium supplied with 1% glycerol, 6 mM ISO/DMAA 3:1, and 0.1 mM isopropyl β-ᴅ-1-thiogalactopyranoside (IPTG) inducer. In comparison with the negative control of wild-type E. coli BL21 (DE3), all strains successfully

• and DMAPP. Given that the commercial DMAA is cheaper than ISO, our result in merely using DMAA should be helpful in decreasing the overall cost for the production of other terpenes using this two-step artificial pathway [22]. Optimizing the concentrations of glycerol and IPTG, and fermentation time

• course Three orthogonal experiments were run to examine the effects of varying glycerol and IPTG concentrations and fermentation time, all in an effort to optimize terpentetriene and ent-kaurene production. Given that the carbon source is vital for overproducing natural products in E. coli, and glycerol

Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity

• Jamshid Amiri Moghaddam,
• Huijuan Guo,
• Karsten Willing,
• Thomas Wichard and
• Christine Beemelmanns

Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72

• performed in a 75 L X-Cube Bioreactor (Braun Biotech International) using 30 L of Terrific Broth medium (Carl Roth GmbH) enriched with 4 mL/L glycerol and 60 mg/L kanamycin. Similar to the in vivo culture assays, the culture was cooled to 16 °C at an OD600 of 1 and heterologous production induced with IPTG

Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome trans-sialidase

• Peterson de Andrade,
• Sanaz Ahmadipour and
• Robert A. Field

Beilstein J. Org. Chem. 2022, 18, 208–216, doi:10.3762/bjoc.18.24

• [4]. For instance, hydrophobic pockets in the glycerol- and acetamide-binding subsites have been reported for neuraminidases [10][37] as well as for TcTS, which has a more spacious and hydrophobic active site around C9 of sialic acid [16]. Nonetheless, a simple comparison from the crystal structures

Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

• Emmanuel T. Oluwabusola,
• Olusoji O. Adebisi,
• Fernando Reyes,
• Kojo S. Acquah,
• Mercedes De La Cruz,
• Larry L. Mweetwa,
• Joy E. Rajakulendran,
• Digby F. Warner,
• Deng Hai,
• Rainer Ebel and
• Marcel Jaspars

Beilstein J. Org. Chem. 2021, 17, 2390–2398, doi:10.3762/bjoc.17.156

• Erlenmeyer flask containing 150 mL modified SGG medium (glycerol 10 g, corn steep powder 2.5 g, peptone 5 g, soluble starch 10 g, yeast extract 2 g, CaCO3 3 g, NaCl 1 g, in 1 L H2O, pH adjusted to 7.3) [45]. The flask was left shaking at 160 rpm in a closed system shaker for ten days at 28 °C. Subsequently