GC-MS was performed on a QP5050A system (Shimadzu Corp., Kyoto, Japan) using an Equity-5 column (0.25 mm i.d. × 30 m, 0.25 μm film thickness; Supelco, Inc., Bellefonte, PA, USA). The HPLC consisted of a 626 pump with 996 photodiode array detector (Waters Corp., Milford, MA) equipped with a C-18 column (Inertsil ODS-3, 5 μm, 250 × 4.6 mm ID; GL Sciences, Inc., Tokyo, Japan). 1H and 13C NMR spectra were recorded with tetramethylsilane as the internal standard using JNM-EX270 (270 MHz) and JNM-LA500 (500 MHz) NMR spectrometers (JEOL Ltd., Tokyo, Japan). High resolution mass spectra were obtained with a JMS-T100LC AccuTOF mass spectrometer (JEOL). The seeds used in the present study have been previously described6 (link). They were planted at a depth of 5 mm in pots (8 × 8 × 6 cm deep) containing sand and then incubated in an illuminated growth chamber (FLI-301N; Tokyo, Rikakikai, Co., Ltd., Tokyo, Japan) under a 16-h light/8-h dark cycle at 22 °C.
Jnm ex270
Manufactured by JEOL
Sourced in Japan
The JNM-EX270 is a nuclear magnetic resonance (NMR) spectrometer designed for analytical applications. It features a 270 MHz superconducting magnet and provides high-resolution NMR data for the structural analysis of chemical compounds.
Automatically generated - may contain errors
Lab products found in correlation
Amx 500, by Bruker (3 mentions)
Jms t100 gcv, by JEOL (3 mentions)
Jms sx 102, by JEOL (2 mentions)
Qp5050a system, by Shimadzu (1 mentions)
Inertsil ods 3, by GL Sciences (1 mentions)
626 pump, by Waters Corporation (1 mentions)
996 photodiode array detector, by Waters Corporation (1 mentions)
Accutof jms t100lc mass spectrometer, by JEOL (1 mentions)
Jnm la500, by JEOL (1 mentions)
Jms 700 mass spectrometer, by JEOL (1 mentions)
P 2200 polarimeter, by Jasco (1 mentions)
Jms sx102a, by JEOL (1 mentions)
Synergy mx microplate reader, by Agilent Technologies (1 mentions)
Lct premier spectrometer, by Waters Corporation (1 mentions)
Prep c18 column, by Agilent Technologies (1 mentions)
Steponeplus real time pcr thermal cycling block, by Thermo Fisher Scientific (1 mentions)
Waters 600 hplc, by Waters Corporation (1 mentions)
Phenylacetic acid paa, by Merck Group (1 mentions)
Abi prism 310 genetic analyzer, by Thermo Fisher Scientific (1 mentions)
Agilent 7890a gc, by Agilent Technologies (1 mentions)
6 protocols using jnm ex270
1
Comprehensive Analytical Characterization of Plant Seeds
2
NMR Characterization and Computational Analysis
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2.1 General.
1 H, 13 (link) C, and 19 (link) F NMR spectra were recorded on a JEOL JNM EX-270 ( 1 H: 270 MHz, 13 C: 67.8 MHz, 19 (link) F: 254.05 MHz) spectrometer in CDCl 3 . The chemical shifts for 1 H and 13 (link) C are given in D (ppm) downfield from internal TMS and CDCl 3 , respectively. 19 (link) F NMR chemical shifts are given in D (ppm) upfield from external trifluoroacetic acid. All calculations were performed using Gaussian 16 software. Geometry optimizations, frequency calculations, and single point calculations were performed for all compounds at the B3LYP level of theory using 6-31G(d) basis set for all atoms. Oxidation potentials (E p ox ) were measured in 0.1 M Bu 4 NBF 4 / MeCN at a scan rate of 100 mV/s by cyclic voltammetry using ALS Instruments model 600 A. A platinum disk electrode (º = 1 mm) and a platinum plate (1 cm © 1 cm) were used as working and counter electrodes, respectively. A saturated calomel electrode (SCE) was used as a reference electrode. Preparative electrolysis experiments were carried out with a Hokuto Denko HABF 501 potentiostat/galvanostat. Mass spectra and high resolution-mass spectra were obtained with a Shimadzu GCMS-QP-2000A or JEOL JMS-700 mass spectrometer. 19 (link) F NMR yields were estimated with A,A,A-trifluorotoluene as an internal standard.
1 H, 13 (link) C, and 19 (link) F NMR spectra were recorded on a JEOL JNM EX-270 ( 1 H: 270 MHz, 13 C: 67.8 MHz, 19 (link) F: 254.05 MHz) spectrometer in CDCl 3 . The chemical shifts for 1 H and 13 (link) C are given in D (ppm) downfield from internal TMS and CDCl 3 , respectively. 19 (link) F NMR chemical shifts are given in D (ppm) upfield from external trifluoroacetic acid. All calculations were performed using Gaussian 16 software. Geometry optimizations, frequency calculations, and single point calculations were performed for all compounds at the B3LYP level of theory using 6-31G(d) basis set for all atoms. Oxidation potentials (E p ox ) were measured in 0.1 M Bu 4 NBF 4 / MeCN at a scan rate of 100 mV/s by cyclic voltammetry using ALS Instruments model 600 A. A platinum disk electrode (º = 1 mm) and a platinum plate (1 cm © 1 cm) were used as working and counter electrodes, respectively. A saturated calomel electrode (SCE) was used as a reference electrode. Preparative electrolysis experiments were carried out with a Hokuto Denko HABF 501 potentiostat/galvanostat. Mass spectra and high resolution-mass spectra were obtained with a Shimadzu GCMS-QP-2000A or JEOL JMS-700 mass spectrometer. 19 (link) F NMR yields were estimated with A,A,A-trifluorotoluene as an internal standard.
3
Comprehensive NMR and Mass Spectrometry Analysis
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All 1 H, 13 C, 1 H-1 H COSY, HMBC, HSQC and NOESY NMR spectra of isolated compounds were measured with an AMX-500 (Bruker, Billeria, MA, USA) (500 MHz and 125 MHz). 1 H and 13 C NMR spectra of synthetic compounds were measured with a JNM-EX270 (JEOL, Tokyo, Japan) (270 MHz and 67.5 MHz). Chemical shifts are defined using tetramethylsilane as the internal standard and expressed in δ ppm. Mass spectra were acquired with FD techniques using a JMS-T100GCV (JEOL) or EI techniques by a JMS-SX102A (JEOL). All NMR spectra on AMX-500 were measured at the GC-MS and NMR Laboratory, Faculty of Agriculture, Hokkaido University. Optical rotations were determined on a P-2200 polarimeter (JASCO, Tokyo, Japan) in a φ3. 4 1 and2.
4
Chemical Characterization of Catecholamines
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L-epinephrine bitartrate, L-norepinephrine bitartate, and dopamine hydrochloride were purchased from Tokyo Chemical Industry (Tokyo, Japan). Other chemicals were purchased from Wako Pure Chemical Industries (Osaka, Japan) unless specified otherwise. Fluorescence was measured using a Synergy™ MX microplate reader (BioTek Instruments, Winooski, VT, USA). An AMX 500 (Bruker, Billerica, MA, USA) or JNM-EX 270 (Jeol Ltd., Tokyo, Japan) system was used to obtain nuclear magnetic resonance (NMR) spectra. Tert-butanol or residual solvent was used as an internal standard (D2O: 1 H NMR 1.24 ppm, 13 C NMR: 30.29 ppm; methanol-d4: 1 H NMR 3.30 ppm, 13 C NMR: 49.00 ppm). A LCT Premier spectrometer (Waters, Milford, MA, USA) was used to obtain electrospray ionization mass spectra (ESI MS).
5
Analytical Instrumentation and Chemicals
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Primary analytical instruments and chemicals used were as follows: Waters 600 HPLC (Waters, MA, USA) with an L-column2 ODS column (250 mm × i.d. 4.6 mm; particle size 5 μm); Agilent 218 Purification Systems (Agilent, Santa Clara, CA, USA) with a Prep-C18 column (50 mm × i.d. 30 mm; particle size 5 μm); Agilent 7890A GC (Agilent, CA, USA) with an HP-5 capillary column (30 m × i.d. 0.25 mm); MS spectrometers JEOL JMS-T100GCV, JMS-SX-102 (JEOL, Tokyo, Japan) and Agilent 7000C GC-MS/MS (Santa Clara, CA, USA) with an Agilent HP-5 glass capillary column (Agilent Technologies, 30 m × i.d. 0.32 mm) under the conditions of initial temperature of 100 °C for 1.5 min and heating at a rate of 60 °C min−1 until 300 °C with a carrier gas of He; NMR spectrometers JEOL JNM-EX270 (JEOL, Tokyo, Japan) and Bruker AM 500 (Bruker, Bremen, Germany); ABI Prism 310 Genetic Analyzer (Applied Biosystems, CA, USA); StepOnePlus Real-Time PCR thermal cycling block (Applied Biosystems, CA, USA); trifluoromethanesulfonic acid-d (TfOD, Energy Chemical, Shanghai, China); L-phenylalanine (TCI, Tokyo, Japan); L-phenylalanine-[ring-2H5] (Sigma-Aldrich, MO, USA); phenylacetic acid (PAA, Sigma-Aldrich, St. Luis, MO, USA). Other chemicals used for preliminary screenings in the present study were purchased from TCI and Wako (Osaka, Japan).
6
Characterization of Diacetonamine Derivatives
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Electron ionization mass spectrometry (EI-MS), field desorption mass spectrometry (FD-MS), and field desorption high-resolution mass spectrometry (FD-HR-MS) were conducted using MS spectrometers JMS-T100GCV and JMS-SX-102 (JEOL, Tokyo, Japan). 1H-/13C-NMR spectra were recorded using a JEOL JNM-EX270 (JEOL, Tokyo, Japan) at 270/67.5 MHz and a Bruker AMX-500 (Bruker, Billerica, MA, USA) at 500/125 MHz.
Diacetonamine hydrogen oxalate (1a ) was purchased from Sigma-Aldrich (St. Louis, MO, USA), and diacetonamine hydrochloride (1b ) and N-acetyldiacetonamine (2 ) were prepared from 1a . As another chemical derivatizable from 1 , diacetone acrylamide (3 ) was purchased from Wako (Osaka, Japan), while a β-amino acid, 3-amino-3-metylbutyric acid (4 ), used as a negative control was purchased from Combi-Blocks (San Diego, CA, USA). Their chemical structures are shown in Fig. 2 .![]()
Diacetonamine hydrogen oxalate (
Structures of diacetonamine and its related chemicals
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