Development of N-F fluorinating agents and their fluorinations: Historical perspective

• Teruo Umemoto,
• Yuhao Yang and
• Gerald B. Hammond

Beilstein J. Org. Chem. 2021, 17, 1752–1813, doi:10.3762/bjoc.17.123

A systems-based framework to computationally describe putative transcription factors and signaling pathways regulating glycan biosynthesis

• Theodore Groth,
• Rudiyanto Gunawan and
• Sriram Neelamegham

Beilstein J. Org. Chem. 2021, 17, 1712–1724, doi:10.3762/bjoc.17.119

• /glycoproteomics-based mass spectrometry, would further support the proposed TF–glycogene relationships [43]. Some caveats in our analysis are important to note. First, we only used selected values of RP and ρ to filter TF–glycogene relationships from the Cistrome Cancer DB. Further studies are needed in order to

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

• the presence of 10 mM MgCl2. Enzyme products were extracted from the assays with hexane and analyzed using gas chromatography–mass spectrometry. Myrcene (9); (E)-β-ocimene (10); (Z)-β-ocimene (11); linalool (5); (E,E)-α-farnesene (12); (E)-β-caryophyllene (1); (E,E)-β-springene (13); (E,E,E)-α

Copper-mediated oxidative C−H/N−H activations with alkynes by removable hydrazides

• Feng Xiong,
• Bo Li,
• Chenrui Yang,
• Liang Zou,
• Wenbo Ma,
• Linghui Gu,
• Ruhuai Mei and
• Lutz Ackermann

Beilstein J. Org. Chem. 2021, 17, 1591–1599, doi:10.3762/bjoc.17.113

• determined by 1H NMR spectroscopy. Chromatographic separation was carried out on silica gel 60H (200–300 mesh) manufactured by Qingdao Haiyang Chemical Group Co. (China). High-resolution mass spectrometry (HRMS) was measured on a Thermo-DFS mass spectrometer. NMR spectra were recorded on a JEOL 600 NMR

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

• conditions, under laser irradiation, and the biocompatibility make it possible to conclude that the design of these compounds is promising for mass spectrometry, for catalysts for hydrogen production, and for photothermal cancer therapy. Representatives of isomeric bisoxindoles. Isoindigo-based OSCs with the

Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate

• Eleni Dimitriou and
• Gavin J. Miller

Beilstein J. Org. Chem. 2021, 17, 1527–1532, doi:10.3762/bjoc.17.110

• % NaHCO3, EtOH, THF, rt, 24 h, 72%. Supporting Information Supporting Information File 218: Detailed experimental protocols and characterisation data; spectral NMR data (1H, 13C, 31P and HSQC NMR for compounds 2–5, 7–14, 16–18, 20 and 21). Acknowledgements We thank the EPSRC UK National Mass Spectrometry

Breaking paracyclophane: the unexpected formation of non-symmetric disubstituted nitro[2.2]metaparacyclophanes

• Suraj Patel,
• Tyson N. Dais,
• Paul G. Plieger and
• Gareth J. Rowlands

Beilstein J. Org. Chem. 2021, 17, 1518–1526, doi:10.3762/bjoc.17.109

• oxidation. Treatment with sulfuric acid returned unreacted starting material along with a trace of what is almost certainly, according to mass spectrometry, a bis(sulfonic acid), although with the quantities isolated, we were unable to determine which isomer. Reaction with triflic acid or perchloric acid

• . ESIMS was recorded on a Dionex UltiMate 3000. High-resolution mass spectrometry was performed using a ThermoScientific Q Exactive Focus Hybrid Quadrupole-Orbitrap mass spectrometer or a Bruker Daltonics MicrOTOF spectrometer. Infrared spectroscopy of compounds was completed on a ThermoFisher Nicolet iS5

Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols

• Jie Zheng,
• Shuyu Meng and
• Quanrui Wang

Beilstein J. Org. Chem. 2021, 17, 1481–1489, doi:10.3762/bjoc.17.104

• isolated products as well as copies of NMR spectra and XRPD data for compound 21. Supporting Information File 182: Experimental section. Acknowledgements We thank Mr. G. Tang for acquiring high-resolution mass spectrometry data. Funding The authors acknowledge the financial support from the National

Design, synthesis and photophysical properties of novel star-shaped truxene-based heterocycles utilizing ring-closing metathesis, Clauson–Kaas, Van Leusen and Ullmann-type reactions as key tools

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2021, 17, 1374–1384, doi:10.3762/bjoc.17.96

• mixture of EtOAc and petroleum ether. Characterization of the intermediates and final compounds were performed using 1H and 13C NMR, mass spectrometry and IR spectroscopy. FTIR spectra of the compounds were recorded on an Aligent FTIR spectrometer (ATR module of Cary 630 FTIR, Agilent Technologies) from

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

• Marine Vallet Filip Kaftan Veit Grabe Fatemeh Ghaderiardakani Simona Fenizia Ales Svatos Georg Pohnert Thomas Wichard Research Group Phytoplankton Community Interactions, Max Planck Institute for Chemical Ecology, Jena, Germany Research Group Mass Spectrometry/Proteomics, Max Planck Institute for

• used mass spectrometry profiling and imaging techniques with high spatial resolution and sensitivity to gain a new perspective on the mutualistic interactions between bacteria and macroalgae. Using atmospheric pressure scanning microprobe matrix-assisted laser desorption/ionisation high-resolution mass

• distributions of metabolites and identifying specific symbiotic bacteria. Keywords: algae; AP-SMALDI; ectoine; holobiont; high-resolution mass spectrometry; mass spectrometry imaging; marine bacteria; Ulva; Introduction In intertidal zones with high temporal and spatial ecosystem variations, bacteria and

Structural effects of meso-halogenation on porphyrins

• Keith J. Flanagan,
• Maximilian Paradiz Dominguez,
• Zoi Melissari,
• Hans-Georg Eckhardt,
• René M. Williams,
• Dáire Gibbons,
• Caroline Prior,
• Gemma M. Locke,
• Alina Meindl,
• Aoife A. Ryan and
• Mathias O. Senge

Beilstein J. Org. Chem. 2021, 17, 1149–1170, doi:10.3762/bjoc.17.88

• were measured with a Stuart SP-10 melting point apparatus. A Bruker Advance III 400 MHz spectrometer was employed for 1H (400.13 MHz), and 13C (100.61 MHz) NMR spectra. All NMR experiments were performed at room temperature. Mass spectrometry analysis was performed with a Q-Tof Premier Waters MALDI

Application of the Meerwein reaction of 1,4-benzoquinone to a metal-free synthesis of benzofuropyridine analogues

• Rashmi Singh,
• Tomas Horsten,
• Rashmi Prakash,
• Swapan Dey and
• Wim Dehaen

Beilstein J. Org. Chem. 2021, 17, 977–982, doi:10.3762/bjoc.17.79

• support. KU Leuven (Project C14/19/78). R. S. thanks IIT (ISM) Dhanbad for a graduate fellowship. Mass spectrometry was made possible by the support of the Hercules Foundation of the Flemish Government (grant 20100225-7).

DNA with zwitterionic and negatively charged phosphate modifications: Formation of DNA triplexes, duplexes and cell uptake studies

• Yongdong Su,
• Maitsetseg Bayarjargal,
• Tracy K. Hale and
• Vyacheslav V. Filichev

Beilstein J. Org. Chem. 2021, 17, 749–761, doi:10.3762/bjoc.17.65

• was confirmed by electrospray ionization mass spectrometry (ESIMS) in the negative mode (Table 1). For clarity, we introduced the following nomenclature of the ONs synthesised. The prefix 5ʼ- or 3ʼ- with either N+ or Ts- means that the first phosphate at the 5ʼ- or 3ʼ-end was modified; m-N+ or m-Ts

• Information Supporting Information File 62: Experimental part. Acknowledgements Manawatu Microscopy and Imaging Centre, NMR and mass spectrometry facilities at Massey University, and the assistance of Mr. Raoul Solomon, Dr. Patrick J. B. Edwards, and Mr. David Lun are gratefully acknowledged. We thank Dr

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

• ). Ugi product 6aaa (first letter – isocyanide code, second letter – amine code, third – carboxylic acid code) was the first to isolate in our trials and its structure was confirmed by X-ray analysis (Figure 3) in addition to mass spectrometry, elemental analysis, 1H and 13C NMR data. Compound 6

[2 + 1] Cycloaddition reactions of fullerene C₆₀ based on diazo compounds

• Yuliya N. Biglova

Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55

• 35 [92] and 36–38 (Figure 4) [93]. A synthesis based on benzo-18-crown-6 to give 39 showed that attachment of the crown ether to the surfaces of fullerene molecules makes it easier to detect them by mass spectrometry [94]. This method was used to incorporate benzocrown ether residues in order to

Synthesis and properties of oligonucleotides modified with an N-methylguanidine-bridged nucleic acid (GuNA[Me]) bearing adenine, guanine, or 5-methylcytosine nucleobases

• Naohiro Horie,
• Takao Yamaguchi,
• Shinji Kumagai and
• Satoshi Obika

Beilstein J. Org. Chem. 2021, 17, 622–629, doi:10.3762/bjoc.17.54

• acetate buffer (pH 7.0). The purity and structure of the oligonucleotides were confirmed by HPLC and MALDI–TOF mass spectrometry, respectively. UV melting experiments and melting profiles The UV melting experiments were carried out using SHIMADZU UV-1650PC and SHIMADZU UV-1800 spectrometers equipped with

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

Amino- and polyaminophthalazin-1(2H)-ones: synthesis, coordination properties, and biological activity

• Zbigniew Malinowski,
• Emilia Fornal,
• Agata Sumara,
• Renata Kontek,
• Karol Bukowski,
• Beata Pasternak,
• Dariusz Sroczyński,
• Joachim Kusz,
• Magdalena Małecka and
• Monika Nowak

Beilstein J. Org. Chem. 2021, 17, 558–568, doi:10.3762/bjoc.17.50

• with a donor nitrogen atom could result in the formation of complexes following a different way of coordination with the metal ion than described in the literature [41]. The complexing properties of compounds 5i, 6d, and 7 were investigated by mass spectrometry (ESIMS). The spectra were recorded after

Synthesis and physicochemical evaluation of fluorinated lipopeptide precursors of ligands for microbubble targeting

• Masayori Hagimori,
• Estefanía E. Mendoza-Ortega and
• Marie Pierre Krafft

Beilstein J. Org. Chem. 2021, 17, 511–518, doi:10.3762/bjoc.17.45

• was stepwisely elongated, and eventually conjugated with the (perfluoroalkyl)ethyl acids (Scheme 2). After the cleavage from the resin, the Fmoc groups of the amino acids were removed, and the F-lipopeptides were purified using a dialysis membrane. According to mass spectrometry, FTIR, and HPLC

• Information Supporting Information File 46: Mass spectrometry and FTIR data as well as RP-HPLC chromatograms of lipopeptides 1–4. Funding The work was supported by JSPS KAKENHI Grant Number JP18KK0439 and JP20K08139. We also acknowledge CONACYT (Mexico) for a Ph.D. fellowship (E.E.M.O., grant #459199).

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

• mass spectrometry and so it was converted to carboxylic acids 14 and 15 by the treatment with silica gel and NaOH, respectively, in order to confirm its identity. A possible mechanism for the formation of 13 from 5n could involve the formation of a terminal carbocation from trichloroalkanone 8n

• Supporting Information File 58: Detailed experimental procedures and NMR spectra for all compounds referenced. Acknowledgements We thank Mr Martin Annau for his valuable assistance in NMR interpretation and structure elucidation, Mrs Susanne Ries for performing the mass spectrometry measurements and Dr

Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines

• Wilfred J. M. Lewis,
• David M. Shaw and
• Jeremy Robertson

Beilstein J. Org. Chem. 2021, 17, 334–342, doi:10.3762/bjoc.17.31

• diamond ATR module, and νmax values are expressed in cm−1. HRMS measurements were performed by the Mass Spectrometry Service at the Chemistry Research Laboratory, University of Oxford, using a Bruker microTOF spectrometer. Values of m/z are calculated to 0.0001 Daltons from the chemical formula, and all

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

• (t), doublet of doublets (dd), doublet of doublets of doublets (ddd), broad (br), and quadruplet of triplets (qt) as abbreviations. Analyses and assignments were made using 1D (1H, 13C, and J-modulated spin–echo (Jmod)) and 2D NMR experiments (COSY and HSQC). High-resolution mass spectrometry (HRMS

¹⁹F NMR as a tool in chemical biology

• Diana Gimenez,
• Aoife Phelan,
• Cormac D. Murphy and
• Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

• ). Each independent intermediate was characterized on the basis of its 19F NMR chemical shift and the kinetics by which each species formed or decayed were evaluated in real-time. By combining the 19F NMR data with that provided by complementary analytical techniques, mass spectrometry (electrospray

• widely used by those investigating the biodegradation of fluorinated xenobiotics, with researchers more commonly relying on liquid or gas chromatography–mass spectrometry methods. Objectively, these techniques are much more sensitive than 19F NMR, provide more structural information and are probably more

Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams

• Michał M. Więcław and
• Bartłomiej Furman

Beilstein J. Org. Chem. 2021, 17, 115–123, doi:10.3762/bjoc.17.12

• -5-yl)-iminosugars, using 2,3,5-tri-O-benzyl-ᴅ-ribofuranose- and -arabinofuranose-derived lactams as substrates were made. Very unexpectedly, we failed to isolate such products although we did observe their formation via mass spectrometry of the reaction mixtures. Employing alternative procedures did