Synthesis and properties of 6-alkynyl-5-aryluracils

• Ruben Manuel Figueira de Abreu,
• Till Brockmann,
• Alexander Villinger,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 898–911, doi:10.3762/bjoc.20.80

• ). Samples were ionized by electron impact ionization (EI) on an Agilent 6890/5973 or Agilent 7890/5977 GC–MS equipped with a HP-5 capillary column using helium carrier gas or by electron spray ionization (ESI) on an Agilent 1200/6210 time-of-flight (TOF) LC–MS. X-ray single-crystal structure analysis was

Activity assays of NnlA homologs suggest the natural product N-nitroglycine is degraded by diverse bacteria

• Kara A. Strickland,
• Brenda Martinez Rodriguez,
• Ashley A. Holland,
• Shelby Wagner,
• Michelle Luna-Alva,
• David E. Graham and
• Jonathan D. Caranto

Beilstein J. Org. Chem. 2024, 20, 830–840, doi:10.3762/bjoc.20.75

• , 4.6 × 150 mm) and connected to an Agilent 6230 TOF mass spectrometer with electrospray ionization (ESI). Analyses used an isocratic mixture containing 65% water, 25% acetonitrile, and 10% isopropanol at a flow rate of 0.5 mL/min. The mass spectrometer was run in the negative ion mode with a probe

Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions

• Martyn Jevric,
• Julian Klepp,
• Johannes Puschnig,
• Oscar Lamb,
• Christopher J. Sumby and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2024, 20, 823–829, doi:10.3762/bjoc.20.74

• alkoxytriphenylphosphonium chloride (26, R = Bn), which then slowly rearranged over 24 hours at 83 °C in DCE, eliminating triphenylphosphine oxide (Figure 2). A single ion was observed in the ESI mass spectrum for the intermediate at m/z 571.1 corresponding to the [M + PPh3 − H]+, and in the 1H NMR, the H4 adjacent to the

New variochelins from soil-isolated Variovorax sp. H002

• Jabal Rahmat Haedar,
• Aya Yoshimura and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2024, 20, 692–700, doi:10.3762/bjoc.20.63

• standards (CD3OD: δH 3.31, δC 49.0). LC–MS experiments and ESI–TOF MS/MS analyses were performed with an amaZon SL-NPC (Bruker Daltonics) or LCMS-2020 (Shimadzu) spectrometer coupled with a Shimadzu HPLC system equipped with an LC-20AD intelligent pump. GC–MS experiments were performed with a Shimadzu

Discovery of unguisin J, a new cyclic peptide from Aspergillus heteromorphus CBS 117.55, and phylogeny-based bioinformatic analysis of UngA NRPS domains

• Sharmila Neupane,
• Marcelo Rodrigues de Amorim and
• Elizabeth Skellam

Beilstein J. Org. Chem. 2024, 20, 321–330, doi:10.3762/bjoc.20.32

• and 700 nm. The MS was optimized using the following conditions: interface voltage 4.5 kV; interface temperature 350 °C; DL temperature 250 °C; heat block 200 °C; ESI mode, acquisition range 100 to 1000 Da; nebulizing gas 1.5 L min−1; drying gas flow 15 L min−1. The fractionation of the sample was

Synthesis of the 3’-O-sulfated TF antigen with a TEG-N₃ linker for glycodendrimersomes preparation to study lectin binding

• Mark Reihill,
• Hanyue Ma,
• Dennis Bengtsson and
• Stefan Oscarson

Beilstein J. Org. Chem. 2024, 20, 173–180, doi:10.3762/bjoc.20.17

• electrospray ionisation (ESI) in positive mode. MALDI–TOF mass spectrometry data were recorded on a Scientific Analysis Instruments MALDI–TOF mass spectrometer in reflectron mode for oligosaccharides and in linear mode for glycoconjugates. Samples were prepared by pre-mixing 1 µL of a solution containing the

Photoinduced in situ generation of DNA-targeting ligands: DNA-binding and DNA-photodamaging properties of benzo[c]quinolizinium ions

• Julika Schlosser,
• Olga Fedorova,
• Yuri Fedorov and
• Heiko Ihmels

Beilstein J. Org. Chem. 2024, 20, 101–117, doi:10.3762/bjoc.20.11

• (OCH3), 58.2 (OCH3), 100.1 (C10), 110.1 (C7), 121.5 (C5), 124.4 (C6a), 127.3 (C2), 129.8 (C4), 131.9 (C10a), 135.4 (C1), 136.4 (C3), 139.5 (C6), 144.8 (C4a), 153.4 (C8), 156.4 (C9), 164.1 (CO2CH3); MS (ESI+) m/z: [M+] 298 (100); Anal. calcd for C17H16ClNO8·0.5HClO4: C, 45.58; H, 3.71; N, 3.13; found: C

• ), 142.0 (C4a), 153.5 (C8), 156.4 (C9); MS (ESI+) m/z: [M+] 274 (100); HRMS–ESI+ (m/z): [M]+ calcd. for C15H13NO2Cl, 274.0629; found, 274.0625. 2-Ethyl-8,9-dimethoxybenzo[c]quinolizinium perchlorate (3f) According to GP, a solution (c = 0.95 mM) of 2f (102 mg, 379 µmol) in MeCN (400 mL) was irradiated for

• ), 110.0 (C7), 121.5 (C5), 124.0 (C6a), 129.0 (C4), 130.9 (C10a), 131.4 (C1), 136.2 (C6), 139.3 (C3), 141.9 (C4a), 142.1 (C2), 152.9 (C9), 155.7 (C8); MS (ESI+) m/z: [M+] 268 (100); Anal. calcd for C17H18ClNO6: C, 55.52; H, 4.93; N, 3.81; found: C, 55.71; H, 4.89; N, 3.83. 2-Acetylamino-8,9-dimethoxybenzo

Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines

• Pavel S. Silaichev,
• Tetyana V. Beryozkina,
• Vsevolod V. Melekhin,
• Valeriy O. Filimonov,
• Andrey N. Maslivets,
• Vladimir G. Ilkin,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2024, 20, 17–24, doi:10.3762/bjoc.20.3

• , 135.7, 143.8, 152.3, 152.9, 157.3, 162.4; IR (ATR, KBr, cm−1): ν 3402, 3316, 3201, 1700, 1688, 1649, 1629, 1594, 1568, 1520, 1497, 1476, 1454, 1444, 1426, 1386, 1358, 1335, 1311, 1276, 1264, 1248, 1194, 1090, 1057, 1028; HRMS–ESI-TOF (m/z): [M + H]+ calcd for C16H19N8O2+, 355.1625; found: 355.1628. (Z

• , 174.5; IR (ATR, KBr, cm−1): ν 3400, 3359, 3255, 1625, 1602, 1563, 1554, 1508, 1495, 1483, 1455, 1436, 1425, 1402, 1385, 1356, 1332, 1319, 1303, 1283, 1257, 1215, 1151, 1095, 1067, 1053, 1035, 1011; HRMS–ESI-TOF (m/z): [M + H]+ calcd for C13H14N7S+, 300.1026; found, 300.1031. X-ray structure

Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes

• Nedra Touj,
• François Mazars,
• Guillermo Zaragoza and
• Lionel Delaude

Beilstein J. Org. Chem. 2023, 19, 1947–1956, doi:10.3762/bjoc.19.145

• carbenes with a strong base, followed by their nucleophilic addition onto carbon disulfide. The nine products obtained were characterized by 1H and 13C NMR spectroscopy, FTIR spectroscopy, HR–ESI mass spectrometry, and elemental analysis. Moreover, the molecular structures of two CAAC·CS2 and two MIC·CS2

Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates

• Xing Liu,
• Wenjing Shi,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1923–1932, doi:10.3762/bjoc.19.143

• , 125.5, 117.4, 109.9, 95.0, 52.3, 44.4, 37.0, 20.9 ppm; IR (KBr) ν: 2960, 2936, 2870, 2211, 1717, 1626, 1498, 1445, 1367, 1268, 1193, 1112, 1090, 1009, 903, 868, 815 cm−1; HRMS–ESI TOF (m/z): [M + Na]+ calcd for C34H26N4O2Na, 545.1956; found, 545.1948. General procedure for the preparation of

• , 127.5, 127.0, 124.4, 111.6, 110.4, 52.2, 51.1, 44.4, 36.8 ppm; IR (KBr) ν: 2924, 2853, 1721, 1608, 1484, 1456, 1430, 1340, 1170, 812 cm−1; HRMS–ESI TOF (m/z): [M + H]+ calcd for C34H27ClN3O4, 576.1685; found, 576.1683. General procedure for the preparation of dihydrospiro[indoline-3,5'-[1,2]diazepines

• cm−1; HRMS–ESI TOF (m/z): [M + Na]+ calcd for C34H28ClN4O3SNa, 595.1774; found, 595.1765. The crystallographic data of compound 7a (CCDC 2280223) have been deposited at the Cambridge Crystallographic Database Centre. Single crystal structure of the spiro compound 7a. Representative [4 + 3

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• (m, 2H), 3.02–2.99 (m, 4H), 1.63–1.51 (m, 6H); MS–ESI− (m/z): 315 ([M − H − piperidine]−, 100). 2,6-Dibromo-4-(4-bromophenyl)pyridine-3,5-dicarbonitrile (3). A mixture of compound 2 (1.16 g, 2.89 mmol, 1 equiv) and POBr3 (2.49 g, 8.68 mmol, 3 equiv) was heated with stirring in an oil bath at 170 °C

• obtained as bright yellow powder. Mp > 200 °C; 1H NMR (400 MHz, CDCl3) 8.10 (d, J = 1.6 Hz, 4H), 7.86 (d, J = 8.5 Hz, 2H), 7.76 (d, J = 8.5 Hz, 2H), 7.71 (d, J = 8.7 Hz, 4H), 7.48 (dd, J = 7.8, 1.9 Hz, 4H), 1.46 (s, 36H); MS–ESI+ (m/z): 839 ([M + H]+, 100); Anal. calcd for C53H52BrN5: C, 75.88; H, 6.25; N

• , 129.64, 127.20, 125.71, 124.18, 116.57, 114.00, 112.34, 103.64, 99.21, 98.30, 34.90, 31.81; MS–ESI+ (m/z): 856 ([M + H]+, 100). Next, potassium carbonate (69 mg, 0.5 mmol, 1 equiv) was added to a solution of 2,6-bis-(3,6-di-tert-butyl-9H-carbazol-9-yl)-4-(4-(trimethylsilylethynyl)phenyl)pyridine-3,5

Substituent-controlled construction of A₄B₂-hexaphyrins and A₃B-porphyrins: a mechanistic evaluation

• Seda Cinar,
• Dilek Isik Tasgin and
• Canan Unaleroglu

Beilstein J. Org. Chem. 2023, 19, 1832–1840, doi:10.3762/bjoc.19.135

• certain time intervals within 2 hours and examined by ESI LC–MS. Throughout the high-resolution electrospray-ionization time-of-flight (HRESI–TOF) mass analysis of the reaction mixture at 0 °C, the following peaks were observed: m/z = 246.0366 ([M + H]+ calcd for C11H5F5N, 246.0337), m/z = 857.1468 ([M

Selectivity control towards CO versus H₂ for photo-driven CO₂ reduction with a novel Co(II) catalyst

• Lisa-Lou Gracia,
• Philip Henkel,
• Olaf Fuhr and
• Claudia Bizzarri

Beilstein J. Org. Chem. 2023, 19, 1766–1775, doi:10.3762/bjoc.19.129

• high-resolution mass spectrometry (ESI), where it was shown the fragment corresponding to complex 1 that lost one isothiocyanate, [M − NCS]+, as the primary signal. Elemental analysis matched the calculated values, incorporating an additional MeOH molecule. Recrystallization was afforded by re

Unprecedented synthesis of a 14-membered hexaazamacrocycle

• Anastasia A. Fesenko and
• Anatoly D. Shutalev

Beilstein J. Org. Chem. 2023, 19, 1728–1740, doi:10.3762/bjoc.19.126

• -standard approach [44] (see the Supporting Information File 1 for details). The high-resolution mass spectrum (ESI+) of a mixture of 5 and the impurity, in addition to a peak at m/z = 329.1696 [M + H]+ for compound 5, shows a peak at m/z = 319.1862 [M + H]+, consistent with the molecular formula of

• structure (see Supporting Information File 1). The high-resolution mass spectrum (ESI+) confirmed its chemical formula as C12H16N12. Thus, we found that, in contrast to the reported data [40], the reaction between imidate 4 and hydrazine hydrate (4 equiv) in refluxing EtOH for 2 h afforded macrocycle 5 in a

• to 1D and 2D NMR, and HRMS (ESI+) data, the product obtained was triazolo[1,5-c]pyrimidine 13 instead of the expected macrocycle 11. The structure 13 was unambiguously confirmed by its synthesis directly from pyrazolopyrimidine 8 (ethyl orthoformate, 1.3 equiv of HCOOH, reflux, 15 h). Analogously, no

Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

• Ken-ichi Nakashima,
• Naohito Abe,
• Masayoshi Oyama,
• Hiroko Murata and
• Makoto Inoue

Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117

• Hitachi U-2900 spectrometer. ECD spectra were acquired with a JASCO J-820 spectropolarimeter and IR spectra were recorded using a Shimadzu FTIR-8400S spectrophotometer. NMR spectra were acquired with a JEOL JNM-ECZ 400S spectrometer with tetramethylsilane as an internal standard. ESI–MS data were obtained

Secondary metabolites of Diaporthe cameroonensis, isolated from the Cameroonian medicinal plant Trema guineensis

• Bel Youssouf G. Mountessou,
• Élodie Gisèle M. Anoumedem,
• Blondelle M. Kemkuignou,
• Yasmina Marin-Felix,
• Frank Surup,
• Marc Stadler and
• Simeon F. Kouam

Beilstein J. Org. Chem. 2023, 19, 1555–1561, doi:10.3762/bjoc.19.112

• sulfuric acid before heating. LC–MS chromatograms were recorded with an UltiMate 3000 Series uHPLC (Thermo Fischer Scientific) using a C18 Acquity UPLC BEH column (2.1 × 50 mm, 1.7 µm) connected to an amazon speed ESI-Iontrap-MS (Bruker). Semi-preparative and/or preparative HPLC systems on normal and

• % B in 19.5 min and then maintaining 100% B for 5 min, flow rate 0.6 mL/min, UV–vis detection 200–640 nm) connected to a MaXis ESI-TOF mass spectrometer (Bruker) (scan range 100–2500 m/z, capillary voltage 4500 V, dry temperature 200 °C). NMR spectra were recorded at 25 °C on a Bruker (Billerica, MA

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

• MHz, DMSO-d6) δ (ppm) 196.8, 169.1, 161.2, 148.8, 121.8, 121.0, 117.8, 110.9, 56.0. HRMS–ESI− (m/z): [M]− calcd for C9H6NO3S2: 240.982814; found, 240.982805. DPPH-scavenging activity Determination of antioxidant activity was performed according to the procedure described in the literature [21]. A DMSO

Selective construction of dispiro[indoline-3,2'-quinoline-3',3''-indoline] and dispiro[indoline-3,2'-pyrrole-3',3''-indoline] via three-component reaction

• Ziying Xiao,
• Fengshun Xu,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1234–1242, doi:10.3762/bjoc.19.91

• , 127.9, 127.5, 127.5, 127.1, 127.1, 127.0, 126.2, 125.9, 125.6, 124.9, 110.9, 110.3, 102.3, 62.3, 60.3, 50.0, 49.4, 44.4, 44.2, 42.5, 42.4, 32.9, 29.0, 27.6, 13.5 ppm; IR (KBr) ν: 3504, 3024, 3010, 2995, 2985, 1847, 1711, 1603, 1517, 1400, 1299, 1250, 1053, 953, 841 cm−1; HRMS (ESI-TOF): [M + Na]+ calcd

• , 1526, 1545, 1368, 1285, 1145, 1025, 956, 882 cm−1; HRMS (ESI-TOF): [M + H]+ calcd. for C48H44ClN3O5, 760.2937; found, 760.2921. Crystal structure of dispiro compound 3a. Crystal structure of compound 4a. Representative cascade reactions of Michael adducts of 3-methyleneoxindoles. Proposed reaction

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

• at 0.6 mL/min and the UV–vis detection made at 210 nm and 190–600 nm. The isolates were analyzed on a MaXis ESI-TOF (time-of-flight) mass spectrometer (Bruker Daltonics) for the HRESIMS data, in the positive ionization mode. This was coupled to an Agilent 1260 series HPLC–UV system (Agilent

• , nm (log ε): 196.5 (1.7); NMR data (1H NMR: 500 MHz, 13C NMR: 125 MHz in methanol-d4) see Table 1; HRMS–ESI (m/z): [M + Na]+ calcd for C43H68NaO12+, 799.4603; found, 799.4604; [2M + Na]+ calcd for C86H136NaO13+, 1575.9314; found, 1575.9321. Forpinioside C (2): pale yellow oil; +30 (c 0.1, MeOH); UV

• –vis (MeOH) λmax, nm (log ε): 196.5 (1.7); NMR data (1H NMR: 500 MHz, 13C NMR: 125 MHz in methanol-d4) see Table 1; HRMS–ESI (m/z): [M – H2O + H]+ calcd for C43H67O12+, 775.4627; found, 775.4625; [M + Na]+ calcd for C43H68NaO13+, 815.4552; found, 815.4550; [2M + H]+ calcd for C86H137O26+, 1607.9212

The effect of dark states on the intersystem crossing and thermally activated delayed fluorescence of naphthalimide-phenothiazine dyads

• Liyuan Cao,
• Xi Liu,
• Xue Zhang,
• Jianzhang Zhao,
• Fabiao Yu and
• Yan Wan

Beilstein J. Org. Chem. 2023, 19, 1028–1046, doi:10.3762/bjoc.19.79

• , J = 7.51 Hz, 2H), 6.85–6.88 (m, 2H), 6.77–6.80 (m, 2H), 6.08 (d, J = 8.13 Hz, 2H); 13C NMR (CDCl3, 125 MHz) δ 162.9, 158.1, 151.9, 142.6, 138.2, 138.2, 130.8, 130.3, 128.0, 127.6, 124.6, 123.5, 121.1, 117.5, 116.4, 111.8; HRMS–ESI (m/z): [M + H]+ calcd for C30H17FN2O2S, 489.0995; found, 489.1072

• ) δ 164.1, 163.0, 143.7, 143.4, 138.8, 133.2, 133.0, 131.5, 130.5, 130.3, 130.2, 128.3, 128.0, 124.2, 122.1, 120.6, 115.8; HRMS–ESI (m/z): [M + H]+ calcd for C30H18N2O2S, 471.1089; found, 471.1159. Synthesis of NI-PTZ-CH3 NI-PTZ-CH3 was synthesized with a method similar to that of NI-PTZ-F. The crude

• , 127.1, 123.3, 120.6, 115.8, 21.3; HRMS–ESI (m/z): [M + H]+ calcd for C31H20N2O2S, 485.1245; found, 485.1325. Synthesis of NI-PTZ-OCH3 NI-PTZ-OCH3 was synthesized by a method similar to that of NI-PTZ-F. The crude product was purified by column chromatography (silica gel, DCM/PE 1:5, v:v). The product

Eschenmoser coupling reactions starting from primary thioamides. When do they work and when not?

• Lukáš Marek,
• Jiří Váňa,
• Jan Svoboda and
• Jiří Hanusek

Beilstein J. Org. Chem. 2023, 19, 808–819, doi:10.3762/bjoc.19.61

• detected by ESI–MS analysis of the reaction mixture as it has a different fragmentation pattern (easily loses water – see Supporting Information File 1, Figure S1) than the starting isobaric salt 6a (loses benzonitrile and thiobenzamide). However, all attempts to isolate intermediate 7a have always failed

Digyalipopeptide A, an antiparasitic cyclic peptide from the Ghanaian Bacillus sp. strain DE2B

• Adwoa P. Nartey,
• Aboagye K. Dofuor,
• Kofi B. A. Owusu,
• Anil S. Camas,
• Hai Deng,
• Marcel Jaspars and
• Kwaku Kyeremeh

Beilstein J. Org. Chem. 2022, 18, 1763–1771, doi:10.3762/bjoc.18.185

• and repeated the structure elucidation (see Supporting Information File 1, Table S2, and Figures S30–S37). The resultant structure confirmed the structural information initially obtained from the NMR data in DMSO-d6 solvent. High-resolution ESI mass spectrometry (HRESIMS) sequence tags Furthermore

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

• Konstantin Lebedinskiy,
• Volodymyr Lobaz and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

• /methanol mixture. The purity of the prepared products was considered enough for use in UV experiments without additional purification. Methods. Low-resolution mass spectra were measured with a Shimadzu LCMS-2020 spectrometer. Samples were ionized by electrospray technique (ESI) and detected by quadrupole

• or TOF. The drying and nebulizer gas was nitrogen. High-resolution mass spectra were measured with an Agilent Technologies 6530 Accurate-Mass Q-TOF LC/MS spectrometer. Samples were ionized by electrospray technique (ESI) and detected by quadrupole or TOF. UV–vis spectroscopy spectra were measured

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

• Sasha Hayes,
• Aya C. Taki,
• Kah Yean Lum,
• Joseph J. Byrne,
• Merrick G. Ekins,
• Robin B. Gasser and
• Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

• 2.50 and δC 39.52, respectively. The UHPLC–MS data were recorded on an Ultimate 3000 RS UHPLC coupled to a Thermo Fisher Scientific ISQEC single quadruple ESI mass spectrometer using an analytical Thermo Scientific Accucore C18 (2.6 μm, 80 Å, 150 × 2.1 mm). HRESIMS data was acquired on a Bruker maXis

• II ETD ESI-qTOF. Phenomenex Strata solid phase extraction (SPE) cartridges (3 cc, polypropylene, single fritted) were used for the small-scale marine sponge extractions. GRACE Davisil (35–70 µm, 60 Å) C18-bonded silica was used for pre-absorption work before reversed-phase (RP) HPLC. The preabsorbed

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

• for the purification of ApppI(d2) [21]. HRMS spectra were recorded on a qTOF mass spectrometer using electrospray ionization (ESI) in negative mode. The purity of the products was determined from the 1H and 31P NMR spectra to be ≥95%, unless stated otherwise. ApppI(d2)⋅3.25 and ⋅5.25 TBA salts: ATP

• TBA salt), 22.6, 20.1 (from TBA salt), 13.8 (from TBA salt, used as calibration peak: value marked same as in the earlier characterization of ApppI [20]); 31P NMR (D2O): δ −11.2 d (2JPP = 19.4), −11.7 d (2JPP = 19.4), −23.4 t (2JPP = 19.4); HRMS–ESI (qTOF, m/z): [M − H]− calcd for C15H212H2N5O13P3