Recent advances in the application of isoindigo derivatives in materials chemistry

• Andrei V. Bogdanov and
• Vladimir F. Mironov

Beilstein J. Org. Chem. 2021, 17, 1533–1564, doi:10.3762/bjoc.17.111

• -coating technique, the authors succeeded in obtaining a thin film by immersing a substrate in a polymer solution, followed by slow extraction, accompanied by slow evaporation of the solvent. The device thus obtained showed one of the highest values of hole conductivity of μe = 8.3 cm2⋅V−1⋅s−1 [78]. It was

Total synthesis of ent-pavettamine

• Memory Zimuwandeyi,
• Manuel A. Fernandes,
• Amanda L. Rousseau and
• Moira L. Bode

Beilstein J. Org. Chem. 2021, 17, 1440–1446, doi:10.3762/bjoc.17.99

• , using our previously published methodology in an overall yield of 8% over 8 steps (Scheme 1) [1]. An alternative strategy for the synthesis of 4 was developed so as to avoid a cumbersome continuous extraction step of a triol associated with the established method, in addition to improving the overall

Analogs of the carotane antibiotic fulvoferruginin from submerged cultures of a Thai Marasmius sp.

• Birthe Sandargo,
• Leon Kaysan,
• Rémy B. Teponno,
• Christian Richter,
• Benjarong Thongbai,
• Frank Surup and
• Marc Stadler

Beilstein J. Org. Chem. 2021, 17, 1385–1391, doi:10.3762/bjoc.17.97

• corresponding cultures were deposited at the mycological herbarium of Mae Fah Luang University, Chiang Rai, Thailand, accession number MFLUCC 14-0681. The DNA extraction was performed using an EZ-10 Spin Column Genomic DNA Miniprep kit (Bio Basic Canada Inc., Markham, Ontario, Canada) following the

Antiviral therapy in shrimp through plant virus VLP containing VP28 dsRNA against WSSV

• Santiago Ramos-Carreño,
• Ivone Giffard-Mena,
• Jose N. Zamudio-Ocadiz,
• Alfredo Nuñez-Rivera,
• Ricardo Valencia-Yañez,
• Jaime Ruiz-Garcia,
• Maria Teresa Viana and
• Ruben D. Cadena-Nava

Beilstein J. Org. Chem. 2021, 17, 1360–1373, doi:10.3762/bjoc.17.95

• purification. The plant virus CCMV was produced in California cowpea plants (Vigna ungiculata). The plants were mechanically inoculated with a solution containing the virus. After two weeks, the infected leaves were collected and ground in a virus extraction buffer (0.5 M sodium acetate, 0.08 M magnesium

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

• physicochemical properties can be easily tuned and designed to meet specific requirements; they also offer the possibility to develop convenient methodologies to isolate the product by extraction or precipitation, and thus making the reuse of the DES mixture feasible. The large number of biodegradable raw

• extraction of the product and its separation from the eutectic mixture. However, when the recycling protocol was studied, in order to reuse the DES, at the end of the reaction, water was not added, and the product was extracted by simply adding ethyl acetate and separating the upper, organic phase. The DES

Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides

• Roslyn M. Ray,
• Anders Højgaard Hansen,
• Maria Taskova,
• Bernhard Jandl,
• Jonas Hansen,
• Citra Soemardy,
• Kevin V. Morris and
• Kira Astakhova

Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75

• ’-flouronated base; italics and underlined = 2’-O-methyl base Complementary DNA A-1: (Cy5/AGG CTA TCT AGA ATG TAC) G-3: (Cy5/TCT ATC AAT CTA TCA) Peptide synthesis, purification, and characterization Peptide assembly was carried out by solid-phase peptide synthesis in standard solid-phase extraction filtration

A chromatography-free and aqueous waste-free process for thioamide preparation with Lawesson’s reagent

• Ke Wu,
• Yichen Ling,
• An Ding,
• Liqun Jin,
• Nan Sun,
• Baoxiang Hu,
• Zhenlu Shen and
• Xinquan Hu

Beilstein J. Org. Chem. 2021, 17, 805–812, doi:10.3762/bjoc.17.69

• scaling up the preparation of two pincer-type thioamides, we have successfully developed a convenient process with ethylene glycol to replace ethanol during the workup, including a traditional phase separation, extraction, and recrystallization. The newly developed chromatography-free procedure did not

• the LR upon thio-substitution [11][12][13]. It has been observed that the polarity of compound A is generally similar to the desired products, thus making the purification of the desired products by extraction operations less efficient. Therefore, the purification is rather difficult and usually a

• thionation reactions, considerable efforts have been devoted to the improvement of the workup procedures of these reactions. For example, Soós and co-workers introduced perfluoroalkylated derivatives of LR, which simplified the product isolation via a fluorous reversed-phase solid extraction technique [9][10

Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B

• Takashi Nishiyama,
• Erina Hamada,
• Daishi Ishii,
• Yuuto Kihara,
• Nanase Choshi,
• Natsumi Nakanishi,
• Mari Murakami,
• Kimiko Taninaka,
• Noriyuki Hatae and
• Tominari Choshi

Beilstein J. Org. Chem. 2021, 17, 730–736, doi:10.3762/bjoc.17.62

• material. However, after the workup, extraction, and removal of solvent (in vacuo), the appearance of the TLC plate changed due to the formation of various byproducts. Then, the reaction mixture was purified, but the desired carbodiimide 17a was not obtained, but aminopyrroloquinoline 18 formed through

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

Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents

• Anuj Kumar Chhalodia and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 569–580, doi:10.3762/bjoc.17.51

• stripping apparatus (CLSA) [33], followed by the extraction of the filters with CH2Cl2 and analysis by gas chromatography–mass spectrometry (GC–MS) of the resulting extracts. Most of the compounds were readily identified by the comparison of their mass spectra and retention indices to published data. Every

• extraction to a CLSA [33] for 24 h. The released volatiles were collected on charcoal filters (Chromtech, Idstein, Germany), followed by the extraction of the filters with dichloromethane (50 μL), and analysis of the extracts by GC–MS. For comparison, blank experiments with MB medium alone and with MB agar

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

• 27375T, C. halophilus DSM 26270T and C. indicus DSM 27257T, were collected through a closed-loop stripping apparatus (CLSA) on charcoal [37]. After extraction with dichloromethane the obtained extracts were analyzed by GC–MS (Figure 1). The compounds were identified by the comparison of the recorded EI

Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride

• Beatrice Lansbergen,
• Catherine S. Meister and
• Michael C. McLeod

Beilstein J. Org. Chem. 2021, 17, 404–409, doi:10.3762/bjoc.17.36

• 5m compared to the longer chain substrates (e.g., 5c and 5l) could be explained mechanistically by the formation of a terminal carbocation upon the extraction of a fluorine atom by the aluminium species (Scheme 3). This carbocation could be stabilised to varying degrees by the ketone moiety

CF₃-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry

• Anthony J. Fernandes,
• Armen Panossian,
• Bastien Michelet,
• Agnès Martin-Mingot,
• Frédéric R. Leroux and
• Sébastien Thibaudeau

Beilstein J. Org. Chem. 2021, 17, 343–378, doi:10.3762/bjoc.17.32

An atom-economical addition of methyl azaarenes with aromatic aldehydes via benzylic C(sp³)–H bond functionalization under solvent- and catalyst-free conditions

• Divya Rohini Yennamaneni,
• Vasu Amrutham,
• Krishna Sai Gajula,
• Rammurthy Banothu,
• Murali Boosa and
• Narender Nama

Beilstein J. Org. Chem. 2020, 16, 3093–3103, doi:10.3762/bjoc.16.259

• , variations in the absorption, an inadequate penetrating ability of the radiation into the reaction medium, and further reflection of the microwaves. Nevertheless, the solvent was water, which required long extraction processes compared to solvent-free conditions. Castro and co-workers have also reported the

Chemical constituents of Chaenomeles sinensis twigs and their biological activity

• Joon Min Cha,
• Dong Hyun Kim,
• Lalita Subedi,
• Zahra Khan,
• Sang Un Choi,
• Sun Yeou Kim and
• Chung Sub Kim

Beilstein J. Org. Chem. 2020, 16, 3078–3085, doi:10.3762/bjoc.16.257

• , Sungkyunkwan University, Suwon, Republic of Korea. Extraction and isolation. Extraction and solvent partitions were performed in the same manner as described in [13]. The hexanes-soluble fraction (3 g) was separated over a silica gel column (hexanes/EtOAc 3:1) to yield seven fractions (H1–H7). Fraction H3 (0.4

Secondary metabolites of Bacillus subtilis impact the assembly of soil-derived semisynthetic bacterial communities

• Heiko T. Kiesewalter,
• Carlos N. Lozano-Andrade,
• Mikael L. Strube and
• Ákos T. Kovács

Beilstein J. Org. Chem. 2020, 16, 2983–2998, doi:10.3762/bjoc.16.248

• -treated or untreated mock communities cocultivated for 48 h. DNA extraction Environmental- and semisynthetic-community genomic DNA was extracted from either 250 mg soil or 250 µL bacterial culture, respectively, by using the DNeasy PowerSoil Pro Kit (QIAGEN) and following the manufacturer’s instructions

Nocarimidazoles C and D, antimicrobial alkanoylimidazoles from a coral-derived actinomycete Kocuria sp.: application of ¹J_C,H coupling constants for the unequivocal determination of substituted imidazoles and stereochemical diversity of anteisoalkyl chains in microbial metabolites

• Md. Rokon Ul Karim,
• Enjuro Harunari,
• Amit Raj Sharma,
• Naoya Oku,
• Kazuaki Akasaka,
• Daisuke Urabe,
• Mada Triandala Sibero and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 2719–2727, doi:10.3762/bjoc.16.222

• , Japan). The pH value of the medium was adjusted to 7.0 before sterilization. The inoculated flasks were incubated at 30 °C for 5 days, with rotational shaking at 200 rpm. Extraction and isolation In a similar manner as described in [22], after fermentation, 100 mL of 1-butanol was added to each flask

Leveraging glycomics data in glycoprotein 3D structure validation with Privateer

• Haroldas Bagdonas,
• Daniel Ungar and
• Jon Agirre

Beilstein J. Org. Chem. 2020, 16, 2523–2533, doi:10.3762/bjoc.16.204

• definitions match dictionary standards as well as output multiple helper tools to aid the processes of refinement and model building [24]. Most importantly, Privateer already contains methods that allow the extraction of carbohydrate atomistic definitions to create abstract definitions of glycans in memory

A proposed sustainability index for synthesis plans based on input provenance and output fate: application to academic and industrial synthesis plans for vanillin as a case study

• John Andraos

Beilstein J. Org. Chem. 2020, 16, 2346–2362, doi:10.3762/bjoc.16.196

• from biofermentation, chemical synthesis, and solvent extraction processes. In addition, these plans are compared and ranked according to Borda count and poset (partially ordered set) pairwise dominance analyses using the following attributes: process mass intensity (PMI), sacrificial reagent (SR

• vanillin since this high commodity flavour chemical is ideally suited to the present investigation owing to its varied methods of synthesis spanning classical chemical synthesis, biofermentation, and solvent extraction procedures from the natural source vanilla beans. We chose these particular examples

• , and 4-hydroxybenzaldehyde) [38][39][40][41][42][43]; and five plans involved solvent extraction procedures either by percolation, Soxhlet, or supercritical fluid methods using cured vanilla beans that were either whole or were cut up as starting material [44][45][46]. Results and Discussion

Tools for generating and analyzing glycan microarray data

• Akul Y. Mehta,
• Jamie Heimburg-Molinaro and
• Richard D. Cummings

Beilstein J. Org. Chem. 2020, 16, 2260–2271, doi:10.3762/bjoc.16.187

• aglycone (for example, a glycolipid obtained directly by extraction from a natural origin), an appropriate surface needs to be selected which is compatible with the glycoconjugate. Printing methods Once the decision about the surface to which they are to be attached is made, the glycans are dissolved in

Muyocopronones A and B: azaphilones from the endophytic fungus Muyocopron laterale

• Ken-ichi Nakashima,
• Junko Tomida,
• Tomoe Tsuboi,
• Yoshiaki Kawamura and
• Makoto Inoue

Beilstein J. Org. Chem. 2020, 16, 2100–2107, doi:10.3762/bjoc.16.177

• , Aichi Gakuin University (ECN-279). Fermentation, extraction, and isolation The fungus Muyocopron laterale ECN279 was inoculated onto 50 malt extract agar plates. After incubation at 27 °C for 30 d, the fermented materials were extracted with MeOH (1 L × 3 times, each 48 h) at room temperature (ca. 25 °C

Three new O-isocrotonyl-3-hydroxybutyric acid congeners produced by a sea anemone-derived marine bacterium of the genus Vibrio

• Dandan Li,
• Enjuro Harunari,
• Tao Zhou,
• Naoya Oku and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1869–1874, doi:10.3762/bjoc.16.154

• being shake-cultured at 30 °C at 200 rpm for 5 days, each production culture received 100 mL n-butanol, and the flasks were shaken for an additional 1 h for extraction. The emulsified broth was centrifuged at 6000 rpm for 10 min, and the resulting butanol layers were collected and concentrated in vacuo

One-pot synthesis of isosorbide from cellulose or lignocellulosic biomass: a challenge?

• Isaline Bonnin,
• Raphaël Mereau,
• Thierry Tassaing and
• Karine De Oliveira Vigier

Beilstein J. Org. Chem. 2020, 16, 1713–1721, doi:10.3762/bjoc.16.143

• 1.5 h in an ethanol/water (50:50) mixture at 210 °C, and ii) CIMV (Compagnie Industrielle de la Matière Végétale) technology, where wheat straw was treated during 3.5 h of acetic acid/formic acid/water (50:30:15 m/m/m) extraction at 105 °C and then in the presence of H2O2 and organic acids (peracetic

Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells

• Giacomo Mari,
• Lucia De Crescentini,
• Serena Benedetti,
• Francesco Palma,
• Stefania Santeusanio and
• Fabio Mantellini

Beilstein J. Org. Chem. 2020, 16, 1606–1616, doi:10.3762/bjoc.16.133

• inexpensive starting materials. The purification of the hydrazono-dihydroberberines by sole filtration, avoiding any solvent-consuming steps, such as chromatography, extraction or recrystallization, determines a very simple workup. This aspect, together with the total efficiency in atom economy observed