Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates

• Marcin Kaźmierczak and
• Henryk Koroniak

Beilstein J. Org. Chem. 2020, 16, 756–762, doi:10.3762/bjoc.16.69

• -dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCl) [41] significantly increased the reaction yield (86%). What is more, the reaction byproduct is water-soluble and easy to remove by extraction. Nevertheless, HOBt was still used as an additive. This reagent has recently been reported to exhibit explosive

Direct borylation of terrylene and quaterrylene

• Haruka Kano,
• Keiji Uehara,
• Kyohei Matsuo,
• Hironobu Hayashi,
• Hiroko Yamada and
• Naoki Aratani

Beilstein J. Org. Chem. 2020, 16, 621–627, doi:10.3762/bjoc.16.58

• Discussion According to the literature [8], terrylene was prepared from a 3-(1-naphthyl)perylene by using 8 equivalents of AlCl3 in chlorobenzene at 80 °C for 4 h. The crude product was purified by Soxhlet extraction followed by recrystallization from toluene. After these simple manipulations, the pure

• ]. However, the crude product was not completely purified by Soxhlet extraction and by crystallization in our hands. The borylation reaction of hardly soluble crude quaterrylene gave a deep green suspension. MALDI mass spectrometry of the reaction mixture detected an ion peak at m/z = 1004.5018 (calcd for

Opening up connectivity between documents, structures and bioactivity

• Christopher Southan

Beilstein J. Org. Chem. 2020, 16, 596–606, doi:10.3762/bjoc.16.54

• . Although their expert-curated numbers are lower (i.e., ≈2 million compounds against ≈3700 human proteins), these open sources have the great advantage of being merged within PubChem. Parallel efforts have focused on the extraction of document-to-compound (D-C-only) connectivity. In the absence of molecular

• chemistry publishers. In addition, both the European and US PubMed Central portals now add chemistry look-ups from abstracts and full-text papers. However, the fully automated extraction of DARCLP has not yet been achieved. This stands in contrast to the ability of biocurators to discern these relationships

• journals e) they can be text-mined and d) consequently, over 30 million structures have entered PubChem via automated extraction [3]. Non-document sources: While this article has to be restricted to documents an increasing amount of drug discovery data is beginning to surface on the web that may never be

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

• Pezhman Shiri and
• Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

• 2 days at 100 °C, a solid was obtained, which was then filtered off, washed with distilled water, and dried. In the next step, the surfactant pluronic P123 was removed by the Soxhlet extraction method to produce a white solid. Then, 58 was synthesized using 57 and copper(II) acetate in methanol at

• reflux conditions for one day. The resulting powder was filtered off, washed with methanol, and dried. Finally, excess copper was removed by the Soxhlet extraction method (Scheme 9). The 1,3-dipolar reaction of organic alkynes, organic bromides (or aryldiazonium salts or epoxides), and sodium azide

Architecture and synthesis of P,N-heterocyclic phosphine ligands

• Wisdom A. Munzeiwa,
• Bernard Omondi and
• Vincent O. Nyamori

Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35

• , common extraction with dichloromethane was not applicable, hence solid–liquid extraction with diethylamine was used. Low yields were reported for the 3- and 4-pyridyl analogs due to the difficulty associated with their extraction compared to their 2-pyridyl counterparts [54][55]. Dai and co-workers [63

Oligomeric ricinoleic acid preparation promoted by an efficient and recoverable Brønsted acidic ionic liquid

• Fei You,
• Xing He,
• Song Gao,
• Hong-Ru Li and
• Liang-Nian He

Beilstein J. Org. Chem. 2020, 16, 351–361, doi:10.3762/bjoc.16.34

• oligomerization degree was 4. The reaction has excellent selectivity and no other byproducts were detected except water. More remarkably, a simple stratifying at room temperature will cause the separation of catalyst and product, which means the additional solvent extraction or distillation separation employed in

Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus

• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku,
• Nobuyasu Matsuura,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 297–304, doi:10.3762/bjoc.16.29

• Chemical, Kanagawa, Japan) 1%, and natural seawater collected in Toyama Bay, Toyama, 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 using a rotary shaker at a speed of 200 rpm. Extraction and

Absolute configurations of talaromycones A and B, α-diversonolic ester, and aspergillusone B from endophytic Talaromyces sp. ECN211

• Ken-ichi Nakashima,
• Junko Tomida,
• Takao Hirai,
• Yoshiaki Kawamura and
• Makoto Inoue

Beilstein J. Org. Chem. 2020, 16, 290–296, doi:10.3762/bjoc.16.28

• ) under accession numbers LC424445 (ITS) and LC424442 (26S rDNA). Fermentation, extraction, and isolation The methods of fermentation and extraction of the fungus Talaromyces sp. ECN211 were performed in a similar manner as described previously [9]. The fungus Talaromyces sp. ECN211 was inoculated onto

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

• Jucleiton J. R. Freitas,
• Queila P. S. B. Freitas,
• Silvia R. C. P. Andrade,
• Juliano C. R. Freitas,
• Roberta A. Oliveira and
• Paulo H. Menezes

Beilstein J. Org. Chem. 2020, 16, 168–174, doi:10.3762/bjoc.16.19

• protocol for propargylation of aldehydes based on microwave irradiation should take into account not only the reaction itself but also an effective method for the extraction of the obtained products. Despite the excellent results described on Scheme 1, a factor that must be taken into consideration is the

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

• Soleiman E. Helaly,
• Wilawan Kuephadungphan,
• Patima Phainuphong,
• Mahmoud A. A. Ibrahim,
• Kanoksri Tasanathai,
• Suchada Mongkolsamrit,
• Janet Jennifer Luangsa-ard,
• Souwalak Phongpaichit,
• Vatcharin Rukachaisirikul and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293

• extraction Submerged fermentation was done as described by Chepkirui and co-workers [48], with minor modifications. Pure cultures were inoculated in YMG liquid medium by cutting seven mycelial plugs (1 cm × 1 cm) from an actively growing colony into a 500 mL Erlenmeyer flask containing 200 mL of the same

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

• % yeast extract, 1.5% Pharmamedia (Traders Protein), and 1% Diaion HP-20 (Mitsubishi Chemical Co.). The inoculated flasks were placed on a rotary shaker (200 rpm) at 30 °C for 7 days. Extraction and isolation Extraction and isolation of secondary metabolites from strain KJMT.FP.4.3 were carried out in a

• , tR 12.0 min), together with 7-O-methylrhodolamprometrin (4, 7.2 mg, tR 17.4 min), O-methylSMA93 (5, 7.4 mg, tR 13.2 min), tricinonoic acid (6, 3.7 mg, tR 13.1 min), and cyclonerodiol (7, 5.4 mg, tR 11.3 min) after evaporation and extraction with EtOAc. Rhodolamprometrin (3, 4.0 mg, tR 15.2 min) was

A green, economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones

• Daniel P. Pienaar,
• Kamogelo R. Butsi,
• Amanda L. Rousseau and
• Dean Brady

Beilstein J. Org. Chem. 2019, 15, 2930–2935, doi:10.3762/bjoc.15.287

• enriched/purer in hemiketal 5 than that obtained using THF as the solvent. Pure product was readily obtained in 70% yield after purification by column chromatography. We reasoned that the lower aqueous miscibility of 2MeTHF, as compared to THF, resulted in a more efficient product extraction procedure

Palladium-catalyzed Sonogashira coupling reactions in γ-valerolactone-based ionic liquids

• László Orha,
• József M. Tukacs,
• László Kollár and
• László T. Mika

Beilstein J. Org. Chem. 2019, 15, 2907–2913, doi:10.3762/bjoc.15.284

• reuse of the catalyst was subsequently investigated by the model reaction of 0.5 mmol of 1a and 1.5 equiv of 2a in the presence of 0.5 mol % PdCl2(PPh3)2 at 55 °C for 2 h. After the first extraction of the product from the reaction mixture by the addition of 10 × 5 mL of pentane, 3a was isolated with a

Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering

• Eric J. N. Helfrich,
• Geng-Min Lin,
• Christopher A. Voigt and
• Jon Clardy

Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283

• the number of screens that can be done. Though genetic construction, culturing bacteria, terpenoid extraction, and chromatographic analysis can be carried out (semi-)automatedly, terpenoid structure elucidation constitutes another major bottleneck of these endeavors. At this end, the development of

Emission and biosynthesis of volatile terpenoids from the plasmodial slime mold Physarum polycephalum

• Xinlu Chen,
• Tobias G. Köllner,
• Wangdan Xiong,
• Guo Wei and
• Feng Chen

Beilstein J. Org. Chem. 2019, 15, 2872–2880, doi:10.3762/bjoc.15.281

• extraction temperatures. In our study, we aimed I) to determine whether P. polycephalum releases volatile terpenoids under normal growing conditions and II) to identify and characterize the genes for terpene biosynthesis in P. polycephalum. Our results will enable us to compare terpene chemistry and their

Carbazole-functionalized hyper-cross-linked polymers for CO₂ uptake based on Friedel–Crafts polymerization on 9-phenylcarbazole

• Dandan Fang,
• Xiaodong Li,
• Meishuai Zou,
• Xiaoyan Guo and
• Aijuan Zhang

Beilstein J. Org. Chem. 2019, 15, 2856–2863, doi:10.3762/bjoc.15.279

• . Then the solid product was separated by filtration, and the solid product was washed with first methanol, followed by THF, HCl/H2O 2:1 (v/v) and distilled water successively, further purified by Soxhlet extraction with MeOH for 24 h and then THF for another 24 h. Finally, the product was dried in a

Skeletocutins M–Q: biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa

• Tian Cheng,
• Clara Chepkirui,
• Cony Decock,
• Josphat C. Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2782–2789, doi:10.3762/bjoc.15.270

• speed ion trap, Bruker). Fungal material The fungal specimen was collected by C. Decock and J. C. Matasyoh in the Mount Elgon National Reserve [4]. The dried specimen and corresponding cultures were deposited in the MUCL collection (MUCL accession number: 56074). Extraction of the crude extract A

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

• and ammonium acetate was refluxed in benzene in a Dean–Stark apparatus. The reaction mixture underwent a strong tarring and after standard extraction with aqueous sulfuric acid, the main product 1 was isolated in a low yield (ca. 5%, see Scheme 1). In another experiment a much higher yield was

Acid-catalyzed rearrangements in arenes: interconversions in the quaterphenyl series

• Sarah L. Skraba-Joiner,
• Carter J. Holt and
• Richard P. Johnson

Beilstein J. Org. Chem. 2019, 15, 2655–2663, doi:10.3762/bjoc.15.258

• minutes. After cooling, products were isolated by careful neutralization with saturated aqueous NaHCO3 and extraction with dichloromethane. The crude product mixture was purified by flash chromatography then analyzed using 1H NMR. The presence of oligomeric material was assessed on crude isolated product

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

• coverage of the grains. Extraction of the grains with acetone, followed by partitioning of the aqueous residue with EtOAc and defatting with hexane, provided an enriched extract of non-polar secondary metabolites. Fractionation by reversed-phase preparative HPLC (Figures S1 and S2 in Supporting Information

• profile. Preparative cultivation, extraction and isolation Two preparative-scale cultivations were carried out to produce sufficient quantities of the nanangenine family for characterisation and bioassay. Cultivation conditions were identical with the exception of growth medium. Culture A was prepared

Synthetic terpenoids in the world of fragrances: Iso E Super^® is the showcase

• Alexey Stepanyuk and
• Andreas Kirschning

Beilstein J. Org. Chem. 2019, 15, 2590–2602, doi:10.3762/bjoc.15.252

• of years dating back well before biblical times [2][3]. Plants and resins served as source for perfumes after alcoholic extraction. These extracts were not only used as fragrances but also as medicine (aqua mirabilis), aphrodisiac and elixir of life (aquavitae). In 1882 'Fougere Royale' was created

A toolbox of molecular photoswitches to modulate the CXCR3 chemokine receptor with light

• Xavier Gómez-Santacana,
• Sabrina M. de Munnik,
• Tamara A. M. Mocking,
• Niels J. Hauwert,
• Shanliang Sun,
• Prashanna Vijayachandran,
• Iwan J. P. de Esch,
• Henry F. Vischer,
• Maikel Wijtmans and
• Rob Leurs

Beilstein J. Org. Chem. 2019, 15, 2509–2523, doi:10.3762/bjoc.15.244

• , Supporting Information File 1), preventing the extraction of accurate functional values. The PDE value, which reflects efficacies of both the trans and PSS form, appears to have an optimum for 6f (Figure 4B). Figure 4B also shows more subtle behavior for compounds 4d and 6e, which harbor a PDE value of 0.43

Current understanding and biotechnological application of the bacterial diterpene synthase CotB2

• Ronja Driller,
• Daniel Garbe,
• Norbert Mehlmer,
• Monika Fuchs,
• Keren Raz,
• Dan Thomas Major,
• Thomas Brück and
• Bernhard Loll

Beilstein J. Org. Chem. 2019, 15, 2355–2368, doi:10.3762/bjoc.15.228

• with residual organic waste streams, such as milling or forestry waste. Additionally, the heterologous terpene production minimizes waste generation as the targeted production of a single compound reduces extraction and purification steps [24][25]. Additionally, heterologous production enables protein

• engineering to optimize product ratios or to alter the native product portfolio of the enzyme [9][26][27]. Furthermore, production by engineered microorganisms considerably reduces the cost compared to total chemical synthesis or extraction from natural sources, since the target compounds are produced from

Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.

• Amit Raj Sharma,
• Enjuro Harunari,
• Tao Zhou,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2327–2332, doi:10.3762/bjoc.15.225

• sterilization. The inoculated flasks were incubated at 30 °C on a rotary shaker at 200 rpm for 5 days. Extraction and isolation After fermentation, 100 mL of 1-butanol was added to each production culture flask, and the flasks were allowed to shake for 1 h on a rotary shaker at 200 rpm. The mixture was

• 181.1230 [M − H]− (calcd for C11H17O2, 181.1229). Feeding experiment Feeding experiments were carried out using 13C-labeled precursors, sodium [1-13C]acetate and ʟ-[methyl-13C]methionine. The fermentation, extraction and purification of labeled compounds were performed in the same manner as describe for

Isolation of fungi using the diffusion chamber device FIND technology

• Benjamin Libor,
• Henrik Harms,
• Stefan Kehraus,
• Ekaterina Egereva,
• Max Crüsemann and
• Gabriele M. König

Beilstein J. Org. Chem. 2019, 15, 2191–2203, doi:10.3762/bjoc.15.216

• microorganisms (BCCM/IHEM, Brussels) by extracting DNA using their usual protocols and genomic DNA extraction kits and generation of partial sequences of DNA loci using standard primers of ITS1, ITS2, ITS4, 5.8S, RPBII, tef1α and β-tubulin. Digitalized and formatted DNA sequences were compared to reference

• (Leica, Wetzlar, Germany) and micromorphology was examined with an Olympus BX51 polarizing microscope (Olympus, Shinjuku, Japan) by analysis of conidia and mycelium to support the bioinformatic suggestions. Fermentation, extraction and isolation For cultivation of the marine isolates from the diffusion