Synthesis of the biologically important dideuterium-labelled adenosine triphosphate analogue ApppI(d₂)

• Petri A. Turhanen

Beilstein J. Org. Chem. 2022, 18, 1466–1470, doi:10.3762/bjoc.18.153

• (d2) opens possibilities to quantitative measurements of ApppI in biological samples by mass spectrometry. The synthesized target compound ApppI(d2) was purified by high-performance counter current chromatography and characterized by 1H, 13C, and 31P NMR spectroscopy as well as high-resolution mass

• spectrometry. Keywords: ApppI; ATP; deuterium labelling; HPCCC; mevalonate pathway; NMR; synthesis; Introduction It has become clear and evident that phosphonate chemistry plays a crucial role in drug research and development [1][2][3][4]. There are several phosphonate-containing compounds under research or

Sinensiols H–J, three new lignan derivatives from Selaginella sinensis (Desv.) Spring

• Qinfeng Zhu,
• Beibei Gao,
• Qian Chen,
• Tiantian Luo,
• Guobo Xu and
• Shanggao Liao

Beilstein J. Org. Chem. 2022, 18, 1410–1415, doi:10.3762/bjoc.18.146

• basis of 1D and 2D NMR spectroscopy as well as high-resolution mass spectrometry. The absolute configuration of 1 was established by ECD calculation. Compounds 2 and 3 represent rare examples of naturally occurring 9,9'-bisnorlignans. All the isolated compounds were assayed for their inhibitory effects

Characterization of a new fusicoccane-type diterpene synthase and an associated P450 enzyme

• Jia-Hua Huang,
• Jian-Ming Lv,
• Liang-Yan Xiao,
• Qian Xu,
• Fu-Long Lin,
• Gao-Qian Wang,
• Guo-Dong Chen,
• Sheng-Ying Qin,
• Dan Hu and
• Hao Gao

Beilstein J. Org. Chem. 2022, 18, 1396–1402, doi:10.3762/bjoc.18.144

• ]. The resulted transformant was cultivated in the modified Czapek–Dox medium for four days, and then mycelia were harvested and extracted for analysis. Upon gas chromatography-mass spectrometry (GC–MS) analysis, we observed an additional peak at m/z = 272 [M]+ from the tadA harboring transformant

• , implying that TadA can catalyze the formation of a diterpene hydrocarbon (Supporting Information 1, Figure S1). The crude extract was also subjected to high-performance liquid chromatography–mass spectrometry (HPLC–MS) analysis. It showed that introduction of tadA led to the generation of two products 1

• ionization mass spectrometry (HRESIMS), the molecular formula of 1 was deduced as C20H32, indicating that 1 has five degrees of unsaturation. The 13C NMR spectrum showed that there are four olefinic carbons (δC 153.2, 137.4, 125.1, 118.6) in 1. We thus reasoned that 1 features a tricyclic system

Preparation of an advanced intermediate for the synthesis of leustroducsins and phoslactomycins by heterocycloaddition

• Anaïs Rousseau,
• Guillaume Vincent and
• Cyrille Kouklovsky

Beilstein J. Org. Chem. 2022, 18, 1385–1395, doi:10.3762/bjoc.18.143

• solvent using residual chloroform (7.26 ppm) as an internal reference. 13C NMR spectra were measured at 62.5, 75 or 90 MHz using residual chloroform (77.1 ppm) as an internal reference. High-resolution mass spectrometry (HRMS) analyses were conducted with electro spray ionization (ESI). 6

On drug discovery against infectious diseases and academic medicinal chemistry contributions

• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

• , parallel/combinatorial synthesis, multicomponent chemistry, metal-catalyzed coupling reactions as well as NMR, preparative/analytical liquid chromatography and mass spectrometry). – An improved understanding of molecular pharmacology along with in vitro or in vivo assays to detect various aspects of drug

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

• Merve Karaman,
• Abhishek Kumar Gupta,
• Subeesh Madayanad Suresh,
• Tomas Matulaitis,
• Lorenzo Mardegan,
• Daniel Tordera,
• Henk J. Bolink,
• Sen Wu,
• Stuart Warriner,
• Ifor D. Samuel and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

• synthetic strategy, which itself was synthesized from Br-DiKTa [28] following a Buchwald–Hartwig coupling. Details of the synthesis are found in Supporting Information File 1. The identity and purity of the molecules were verified using a combination of 1H and 13C NMR spectroscopy, high resolution mass

• spectrometry (HRMS) (Figures S1–S24 in Supporting Information File 1), and melting point analysis. We modelled the electron density distribution in DiKTa-OBuIm and DiKTa-DPA-OBuIm using density functional theory (DFT) calculations in the ground state, at the PBE0/6-31G(d,p) level of theory in the gas phase

Thermally activated delayed fluorescence (TADF) emitters: sensing and boosting spin-flipping by aggregation

• Ashish Kumar Mazumdar,
• Gyana Prakash Nanda,
• Nisha Yadav,
• Upasana Deori,
• Upasha Acharyya,
• Bahadur Sk and
• Pachaiyappan Rajamalli

Beilstein J. Org. Chem. 2022, 18, 1177–1187, doi:10.3762/bjoc.18.122

• Supporting Information File 1. Both compounds were further purified by temperature-gradient vacuum sublimation and characterized by 1H and 13C NMR spectroscopy (Figures S9–S12, Supporting Information File 1) as well as high-resolution mass spectrometry. Photophysical studies and DFT calculations The UV–vis

Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones

• Nguyen Tran Nguyen,
• Vo Viet Dai,
• Nguyen Ngoc Tri,
• Luc Van Meervelt,
• Nguyen Tien Trung and
• Wim Dehaen

Beilstein J. Org. Chem. 2022, 18, 1140–1153, doi:10.3762/bjoc.18.118

• structures of the obtained compounds were elucidated by NMR and mass spectrometry. The reaction between 1,5-diphenyl-4-acetyl-3-hydroxy-3-pyrrolin-2-one (4a) and 4-methoxybenzylamine (9a) was chosen to optimize the reaction conditions, such as the reactant ratio and solvent. Heating 2-pyrrolidinone

Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold

• Dmitry Dar’in,
• Grigory Kantin,
• Alexander Bunev and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2022, 18, 1070–1078, doi:10.3762/bjoc.18.109

• spectrum), mass spectrometry and, in the case of compound 10c, by single-crystal X-ray crystallography (Scheme 2). Using compound 10a as the model substrate, we proceeded to screen for suitable reaction conditions that would allow involving this kind of diazo compounds in the TfOH-promoted benzene C

Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials

• Valentin H. K. Fell,
• Joseph Cameron,
• Alexander L. Kanibolotsky,
• Eman J. Hussien and
• Peter J. Skabara

Beilstein J. Org. Chem. 2022, 18, 944–955, doi:10.3762/bjoc.18.94

• refluxed overnight [43]. The result was a dark violet/black material, which was not soluble in common organic solvents, thereby preventing NMR spectroscopy. Also, sublimation failed. However, the mass could be measured with MALDI mass spectrometry, and microanalysis results matched the theoretical values

Morita–Baylis–Hillman reaction of 3-formyl-9H-pyrido[3,4-b]indoles and fluorescence studies of the products

• Nisha Devi and
• Virender Singh

Beilstein J. Org. Chem. 2022, 18, 926–934, doi:10.3762/bjoc.18.92

• transformation than 6e. It is noteworthy here that all the products were purified by column chromatography. A small library of C-3-substituted pyrido[3,4-b]indole derivatives was designed and synthesized which is presented in Figure 4. All the products were characterized using NMR, FTIR and mass spectrometry

Cathodic generation of reactive (phenylthio)difluoromethyl species and its reactions: mechanistic aspects and synthetic applications

• Sadanobu Iwase,
• Shinsuke Inagi and
• Toshio Fuchigami

Beilstein J. Org. Chem. 2022, 18, 872–880, doi:10.3762/bjoc.18.88

• difluorocarbene adduct 5 was detected by high resolution mass spectrometry in addition to products 2, 3, and 4. As already mentioned, SmI2 is a well-known one-electron reducing reagent, and has been used to generate PhSCF2 radicals and perfluoroalkyl radicals from PhSCF2Br and perfluoroalkyl halides, respectively

First series of N-alkylamino peptoid homooligomers: solution phase synthesis and conformational investigation

• Maxime Pypec,
• Laurent Jouffret,
• Claude Taillefumier and
• Olivier Roy

Beilstein J. Org. Chem. 2022, 18, 845–854, doi:10.3762/bjoc.18.85

• ) for compound 2, CCDC deposition number 2167472. Acknowledgements We express our sincere thanks to M. Leremboure and F. Emenegger for mass spectrometry analyses (UCA PARTNER). We also thank H. Billard and J. Colombet, Plateforme CYSTEM – UCA PARTNER (Clermont-Ferrand, FRANCE), for their technical

Synthesis and HDAC inhibitory activity of pyrimidine-based hydroxamic acids

• Virginija Jakubkiene,
• Gabrielius Ernis Valiulis,
• Markus Schweipert,
• Asta Zubriene,
• Daumantas Matulis,
• Franz-Josef Meyer-Almes and
• Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 837–844, doi:10.3762/bjoc.18.84

• chromatography was performed using silica gel 60 (0.040–0.063 mm) (Merck). NMR spectra were recorded on a Bruker Ascend 400 spectrometer (400 MHz and 100 MHz for 1H and 13C, respectively). 1H NMR and 13C NMR were referenced to residual solvent peaks. High-resolution mass spectrometry (HRMS) analyses were carried

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

• obtained after washing and ultracentrifugation. Substrate specificity of UbiA-297 Based on our in silico analysis and previous mass-spectrometry-guided metabolomic analysis of marine Flavobacteria and members of the genus Saccharomonospora [29][30], we anticipated hydroxylated aromatic or even quinoline

• presence of Mg2+ as co-factor. Product formation was monitored after 2 h using high-resolution tandem mass spectrometry (HRMS/MS). Membrane proteins obtained from E. coli BL21 cultures harboring the empty expression pET28 plasmid were used as negative control (Figure S3 in Supporting Information File 1

Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment

• Anas J. Rasras,
• Mohamed El-Naggar,
• Nesreen A. Safwat and
• Raed A. Al-Qawasmeh

Beilstein J. Org. Chem. 2022, 18, 631–638, doi:10.3762/bjoc.18.63

• were obtained from piperidine and pyrrolidine, respectively, as secondary cyclic amine component (Figure 2). The structures of the newly synthesized compounds were confirmed on the basis of their spectral data in particular nuclear magnetic resonance (NMR) and mass spectrometry (MS) techniques. The 1H

Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery

• Man-Ping Li,
• Nan Yang and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56

• competitive guest to control the release of MV and DOX. The structures of the target molecule TBTQ-CB6 and its precursors were characterized by NMR spectroscopy and mass spectrometry. The host–guest chemistry of TBTQ-CB6MV, TBTQ-CB6DOX and TBTQ-CB6SM was investigated by NMR spectroscopy and fluorescence

• synthesized compounds were fully characterized by 1H and 13C NMR spectroscopy and mass spectrometry (see Supporting Information File 1) and the data were found to be consistent with the proposed structures. Host–guest complexation of TBTQ-CB6 with dimethyl viologen (MV). The host–guest complexation between

• host–guest interactions. The target compound TBTQ-CB6 was characterized in detail by NMR spectroscopy and mass spectrometry. The host–guest complexes of TBTQ-CB6 with MV, DOX, and the overexpressed molecule spermine (SM) found within cancer cells are formed in a 1:1 stoichiometry in all cases and with

Substituent effect on TADF properties of 2-modified 4,6-bis(3,6-di-tert-butyl-9-carbazolyl)-5-methylpyrimidines

• Irina Fiodorova,
• Tomas Serevičius,
• Rokas Skaisgiris,
• Saulius Juršėnas and
• Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 497–507, doi:10.3762/bjoc.18.52

• and 100 MHz for 1H and 13C, respectively). 1H NMR and 13C NMR spectra were referenced to residual solvent peaks. High-resolution mass spectrometry (HRMS) analyses were carried out on a Dual-ESI Q-TOF 6520 (Agilent Technologies) mass spectrometer. Photophysical properties were analyzed in 10−5 M

Borylated norbornadiene derivatives: Synthesis and application in Pd-catalyzed Suzuki–Miyaura coupling reactions

• Robin Schulte and
• Heiko Ihmels

Beilstein J. Org. Chem. 2022, 18, 368–373, doi:10.3762/bjoc.18.41

• the neighboring methyl group at the reaction center. The novel compounds 2a, 2b, and 3 were identified and characterized by NMR spectroscopy (1H, 13C, COSY, HSQC, HMBC), melting point, and elemental analysis. In addition, the structure of product 2b was supported by high resolution mass spectrometry

Amamistatins isolated from Nocardia altamirensis

• Till Steinmetz,
• Wolf Hiller and
• Markus Nett

Beilstein J. Org. Chem. 2022, 18, 360–367, doi:10.3762/bjoc.18.40

• Abstract Four new phenolic siderophores were isolated from the actinomycete Nocardia altamirensis along with the known natural product amamistatin B and a putative biosynthetic shunt product. The structures of all compounds were elucidated through 1D and 2D NMR analyses as well as mass spectrometry. The

• conditions. The structures of these natural products were verified by high-resolution mass spectrometry, tandem mass spectrometry as well as 1D and 2D NMR analyses. Their absolute configuration is consistent with the already known amamistatin B according to a comparison of optical rotation values and NOE

Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor

• Yuki Naito,
• Naoki Shida and
• Mahito Atobe

Beilstein J. Org. Chem. 2022, 18, 350–359, doi:10.3762/bjoc.18.39

• column (Mightysil RP-18 GP II 250-4.6 (5 µm), Cica) using a mixture of H2O/MeCN/H3PO4 (60/40/0.1%) as a mobile phase. All chromatograms were recorded using an LC workstation (LabSolutions DB, Shimadzu). Helium gas was used as a carrier gas for the gas chromatography/mass spectrometry (GC–MS) analyses. 1H

Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin imines

• Marco Manenti,
• Leonardo Lo Presti,
• Giorgio Molteni and
• Alessandra Silvani

Beilstein J. Org. Chem. 2022, 18, 303–308, doi:10.3762/bjoc.18.34

• optimized conditions (Table 1, entry 12) followed by flash chromatography, the unprecedented bisoxindole 2a was fully characterized by high-resolution mass spectrometry and by one- and two-dimensional NMR analysis. In particular, from HSQC, HMBC and COSY experiments all single frequencies could be safely

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

• Surendran Amrutha,
• Sankaran Radhika and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

• , but their efficiencies were found to be lower than that of 1,10-phenanthroline. Metal impurities in FeCl3·6H2O were detected by using ICP mass spectrometry. Lipshutz and co-workers prepared nanoparticles from inexpensive iron(III) chloride containing reusable palladium in ppm level and XPhoS as ligand

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

• kindly provided by Prof. Sabine Flitsch, University of Manchester. We thank Dr. Reynard Spiess for providing the HRMS data through the Michael Barber Centre for Collaborative Mass Spectrometry. Funding This work was supported by the Flexible Talent Mobility Account (grant BB/S507957/1), funded by the

Diametric calix[6]arene-based phosphine gold(I) cavitands

• Gabriele Giovanardi,
• Andrea Secchi,
• Arturo Arduini and
• Gianpiero Cera

Beilstein J. Org. Chem. 2022, 18, 190–196, doi:10.3762/bjoc.18.21

• via conventional protocols using (Me2S)AuCl. Notably, the organometallic macrocycles A,B,C(AuCl)2 could be isolated via column chromatography separation. Gold(I) catalysts were subsequently fully characterized by NMR analysis and high-resolution mass spectrometry. The conformation of the catalysts, in