All the reagents and solvents were commercially available and used as received. The 1H-NMR spectra were measured on a Bruker Ascend-400 (Bruker, Billerica, MA, USA) at 400 MHz with TMS as an internal standard. The 13C-NMR spectra were measured on a Bruker Ascend-400 at 100 MHz, and assignments of 13C-NMR spectra were performed by DEPT experiments. The high resolution mass spectra were measured on a AB SCIEX Triple TOF 4600 (AB Sciex, Framingham, MA, USA).
Ascend 400
Manufactured by Bruker
Sourced in Germany, United States, Switzerland
The Ascend 400 is a nuclear magnetic resonance (NMR) spectrometer designed for high-resolution analysis of chemical and biological samples. It operates at a magnetic field strength of 9.4 Tesla, providing precise measurements of molecular structures and compositions.
Automatically generated - may contain errors
Lab products found in correlation
Ultrashield 400 plus, by Bruker (5 mentions)
Deuterated solvent, by Merck Group (2 mentions)
Norell suprasil quartz nmr tubes, by Merck Group (2 mentions)
Rayonet photochemical chamber reactor rpr 200, by Merck Group (2 mentions)
Seveneasy ph meter s20, by Mettler Toledo (2 mentions)
Inova 500 spectrometer, by Agilent Technologies (2 mentions)
Accutof, by JEOL (2 mentions)
Discover system, by CEM Corporation (2 mentions)
Ascend 500, by Bruker (2 mentions)
S 3100 spectrophotometer, by Scinco (2 mentions)
Silica gel 60 pf254, by Merck Group (2 mentions)
D8 focus diffractometer, by Bruker (2 mentions)
Ascend 600, by Bruker (2 mentions)
Acquity photodiode array detector, by Waters Corporation (2 mentions)
Acquity uplc, by Waters Corporation (2 mentions)
230 400 mesh silica gel, by Thermo Fisher Scientific (2 mentions)
Qtof mass detector, by Waters Corporation (2 mentions)
Varian 6000i uv vis nir spectrophotometer, by Agilent Technologies (2 mentions)
Sevenmulti ph mv module, by Thermo Fisher Scientific (2 mentions)
Orion 8103bn ph probe, by Thermo Fisher Scientific (2 mentions)
94 protocols using ascend 400
1
NMR and Mass Spectroscopy Protocol
2
NMR Characterization of Complex Organic Compounds
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1H NMR, 13C NMR, 19F NMR, and 31P NMR spectra were performed on Bruker ASCEND 400 (400 MHz), Bruker ASCEND 600 (600 MHz), and Varian Mercury (300 MHz) spectrometers, as is noted. The 2D and 1D selective NMR spectra (1D NOESY and 1D H-F HOESY) were recorded on Bruker ASCEND 600 (600 MHz) or Bruker ASCEND 400 (400 MHz) spectrometers. Chemical shifts of 1H NMR were expressed in parts per million downfield from tetramethylsilane (TMS) as an internal standard (δ = 0) in CDCl3. Chemical shifts of 13C NMR were expressed in parts per million downfield and upfield from CDCl3 as an internal standard (δ 77.16) or CD3OD (δ 49.00) or CF3COOD (δ 164.2) or traces of solvent. Chemical shifts of 19F NMR were expressed in parts per million upfield from CFCl3. The ethereal solution of diazomethane was prepared as described (Vogel et al., 1989 ). Compounds 1 (Radwan-Olszewska et al., 2011 (link)), 2 (Cox et al., 2005 (link)), 3 (Hamashima et al., 2005 (link)), and 4 (Kim, 2005 (link)) were prepared as described. The NMR data for 25 (McDonald et al., 1985 (link); Huleatt et al., 2015 (link)) was in good agreement. For more information see Supplementary Materials .
3
Melting Point and Spectroscopic Characterization
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The melting points were determined using an SRS-Optimelt automated melting point system. All the reagents and solvents were commercially available and used as received. The 1 H NMR spectra were measured on a Bruker Ascend-400 at 400 MHz with tetramethylsilane as an internal standard. The 13 C NMR spectra were measured on a Bruker Ascend-400 at 100 MHz, and the assignments of the 13 C NMR spectra were performed by DEPT experiments. The high-resolution mass spectra were measured on an AB SCIEX Triple TOF 4600. The IR spectra were recorded on a JASCO FT/IR-4200 spectrometer.
4
Biotransformation of Burkholderia sp. MAK1
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~2 g of wet biomass of Burkholderia sp. MAK1 cells was resuspended in 100 ml of 10 mM potassium phosphate buffer, pH 7.2 supplemented with 15 mM of glucose and 0.25 mM of corresponding substrate and incubated at 30 °C. After bioconversion the cells of Burkholderia sp. MAK1 were separated by centrifugation. The supernatant liquid was vaporized to dryness under reduced pressure. The residue was dissolved in 5 ml of deionized water and purification of the product was carried out using reverse phase chromatography (12 g C-18 cartridge). Prior the purification the column was equilibrated with water. A mobile phase that consisted of water and methanol delivered in the gradient 10:0 → 10:5 elution mode. The collected fractions were analyzed by HPLC-MS. The fractions containing pure product were joined, and the solvent was removed under reduced pressure. 1H NMR spectra were recorded in DMSO-d6 or CDCl3 on Bruker Ascend 400, 400 MHz, and 13C NMR were recorded on Bruker Ascend 400, 100 MHz. Chemical shifts are reported in parts per million relative to the solvent resonance signal as an internal standard.
5
Molecular Structure Analysis of Pigments
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The molecular weight of the two purified red pigments, S-1 and S-2, were analyzed by high-resolution mass spectrometry equipped with an electrospray ionization source (HRESIMS, APEX 7.0T FT-ICR-MS, ESI). Nuclear magnetic resonance (NMR) spectra of the pigments were measured on an instrument (BRUKER Ascend-400) for the operation at 400 MHz for 1H and 100 MHz for 13C NMR. Chemical structure of pigment S-1 was further performed on distortionless enhancement by polarization transfer (DEPT-135), heteronuclear multiple bond connectivity spectroscopy (HMBC), and heteronuclear single quantum correlation (HSQC) for further confirmation of C–H relationship.
6
Comprehensive Spectroscopic Characterization
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Unless otherwise stated, all solvents used in reactions were distilled using common purification protocols [64 ], except DMF and iPr2NH which were dried on molecular sieves (3 Å). Compounds were purified by chromatography on silica gel using different mixtures of eluents as specified. 1H- and 13C-NMR spectra were recorded on a BRUKER Ascend 400 and 500 at 298 K. Fourrier-transform Infrared (FTIR) spectra were recorded on a BRUKER IFS 28 spectrometer. The chemical shifts are referenced to internal tetramethylsilane. High-resolution mass spectra (HRMS) were recorded on different spectrometers: a Bruker MicrOTOF-Q II, a Thermo Fisher Scientific Q-Exactive in electrospray ionisation (ESI) positive mode, and a Bruker Ultraflex III MALDI Spectrometer at CRMPO (Centre Regional de Mesures Physiques de l’Ouest) in Rennes. Reagents were purchased from commercial suppliers and used as received.
7
Spectroscopic Characterization of Compounds
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1H NMR and 13C NMR spectra were recorded using Bruker ARX-400 (Bruker, Billerica, MA, USA) at 400 MHz for 1H and 100.6 MHz for 13C, Bruker Biospin Avance III 400 at 400 MHz for 1H and 100.6 MHz for 13C, Bruker Ascend™-400 at 400 MHz for 1H and 100.6 MHz for 13C or in a Bruker AVANCE™-600 AT 600 MHz for 1H and 150 MHz for 13C spectrometers. Mass spectra were performed in a mass spectrometer with electronic impact ionization (70 eV) Thermo Scientific DSQ II Single Quadrupole GC/MS with Focus GC. The HRMS (Electrospray Ionization Time of Flight, ESI-TOF) mass spectra (MS) were performed on a High Resolution Mass Spectrometer Orbitrap, Q-Exactive (Thermo Fisher Scientific, Waltham, MA, USA) Electrospray Ionization (H-ESI-II), coupled to a Liquid Chromatographer uHPLC Ultimate 2000 Dionex (Thermo Fisher Scientific, Waltham, MA, USA). Matrix-Assisted Laser Desorption/Ionization (MALDI) experiments were performed on a 4700 Proteomics Analyzer MALDI-TOF mass spectrometer. UV–Vis absorption spectra were registered on a Hewlett-Packard 8452A Diode Array spectrophotometer and an AGILENT 8453 spectrophotometer (Santa Clara, CA, USA).
8
Photochemical Reactions and NMR Analysis
9
Synthesis of o-Nitrophenylethyl Caffeate
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Firstly, a mixure of caffee acid (0.9 g, 5.0 mmol, Ⅰ) in thionyl chloride (SOCl2, 20 mL) was heated at 80 °C until the reaction fluid clarified and then distilled under vacuum to remove the excess SOCl2 completely to obtain the intermediate product (caffeoyl chloride, Ⅱ). Secondly, a solution of caffeoyl chloride in dichloromethane (DCM, 20 mL) was added o-nitrophenylethanol (0.8 g, 5.0 mmol, Ⅲ) which was dissolved in 20 mL DCM at room temperature. Next, a catalyst triethylamine TEA, 0.4 mL, 2.9 mmol）was added dropwise, and then the mixture was stirred at 80 °C for 3 h. Finally, the reaction mixture was evaporated under vacuum, and the crude product was purified by silica gel column chromatography (acetone/petroleum ether, 1:4, v/v). The final products were recrystallized from acetone to obtain pure crystals (Fig. 1 B). 1H (CD3COCD3, 400 MHz) and 13C (CD3COCD3, 100 MHz) nuclear magnetic resonance (NMR) spectra were recorded on a spectrometer (Ascend 400, Bruker, USA) and liquid chromatography-mass spectrum (LC-MS) were determined on a mass spectrometer (LCMS-803010500, Shimadzu, Japan).
10
Fluorescent compound synthesis
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4-Hydroxyisobenzofuran-1,3-dione,
trimethyldiphenyl chlorosilicon, iodoethane, and pyridin-2-ylmethanamine
were purchased from Energy Chemical. The other chemicals were analytical
grade and bought commercially. Fluorescence data were recorded on
a Shimadzu RF-5301PC luminescence spectrometer. UV–vis spectra
were obtained on a Shimadu UV-2501PC spectrophotometer. HRMS was performed
with an Agilent 6210 ESI/TOF/MS instrument. The NMR data were acquired
on a Bruker Ascend-400 instrument.
trimethyldiphenyl chlorosilicon, iodoethane, and pyridin-2-ylmethanamine
were purchased from Energy Chemical. The other chemicals were analytical
grade and bought commercially. Fluorescence data were recorded on
a Shimadzu RF-5301PC luminescence spectrometer. UV–vis spectra
were obtained on a Shimadu UV-2501PC spectrophotometer. HRMS was performed
with an Agilent 6210 ESI/TOF/MS instrument. The NMR data were acquired
on a Bruker Ascend-400 instrument.
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