Silica gel 60 (230–400 and 100–200 mesh), pre-coated Kieselgel-60 F-254-TLC plates silica gel (Merck, Darmstadt, Germany), and Sephadex LH-20 (Pharmacia Co. Ltd) were used as packing materials for column chromatography. Isolera-one flash chromatography (Biotage; Suite C Charlotte, NC; USA) was used for flash chromatographic analysis as well as the isolation and purification processes. The compounds were purified using HPLC with a Jasco-pump (PU-980) equipped with a Jasco UV-970 intelligent detector (UV/VIS) at 210 nm. A HPLC semi-preparative Supelco C18-RP-column (250 × 10 mm, 5 μm) was also used. The optical rotation of the isolated compounds was measured by a JASCO (P-2300) polarimeter (Tokyo, Japan). A Bruker 500 Hz (MA, USA) spectrometer was used for recording the 1D NMR, including 1H, 13C, and DEPT-135, and the 2D NMR, including HSQC, HMBC, 1H 1H COSY, and NOESY. All NMR analyses were measured in deuterated methanol (CD3OD) at room temperature. The chemical shifts and coupling constants were given in delta (δ, ppm) and Hertz (Hz), respectively. CD3OD was referenced at δH 4.77 and δH 3.31 ppm in 1H NMR, and at δC 49.14 in 13C NMR. The experimentally measured electronic circular dichroism (ECD) of the compounds were measured in CH3OH by a JASCO-810 spectrometer. The mass spectral data including, LR and HR-MS, were derived by a JEOL (JMS-700) instrument (Tokyo, Japan).
P 2300 polarimeter
Manufactured by Jasco
Sourced in Japan
The P-2300 polarimeter is a laboratory instrument used to measure the optical rotation of a sample. It determines the angle of rotation of the plane of polarized light as it passes through the sample, providing a quantitative measurement of optical activity.
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Lab products found in correlation
Jms 700, by JEOL (2 mentions)
Jms 700 instrument, by JEOL (2 mentions)
600 or 500 hz nmr spectrometer, by Bruker (2 mentions)
Pu 980 pump, by Jasco (2 mentions)
Kieselgel 60 f254, by Merck Group (2 mentions)
Nicolet in10 spectrometer, by Thermo Fisher Scientific (2 mentions)
Avance 400 spectrometer, by Bruker (2 mentions)
Isolera one flash chromatography, by Biotage (1 mentions)
Ft ir 4100 spectrophotometer, by Jasco (1 mentions)
Ltq orbitrap xl spectrometer, by Thermo Fisher Scientific (1 mentions)
Precoated rp 18 f254s plates, by Merck Group (1 mentions)
C18 column, by Merck Group (1 mentions)
Cosmosil c18, by Nacalai Tesque (1 mentions)
Ftir 8400s instrument, by Shimadzu (1 mentions)
Uv 970, by Jasco (1 mentions)
810 polarimeter, by Jasco (1 mentions)
In ertcap tc 1 column, by GL Sciences (1 mentions)
Gc 14b gas chromatography, by Shimadzu (1 mentions)
8 protocols using p 2300 polarimeter
1
Isolation and Characterization of Compounds
2
Characterization of Organic Compounds
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Optical rotations were recorded on a JASCO P-2300 polarimeter (Tokyo, Japan). NMR spectra were measured on a Bruker 500 NMR spectrometer (USA)-500 spectrometer (500 MHz for 1H and 125 MHz for 13C, respectively). All chemical shifts (δ) are given in ppm units with reference to TMS as an internal standard, and coupling constants (J) are reported in Hz. HRMS experiments were performed on Fourier transform ion cyclotron mass spectrometer. High-performance liquid chromatography (HPLC) was performed on an Agilent pump equipped with an Agilent-G1314 variable wavelength UV detector at 254 nm and a semi-preparative reverse-phase column (Econosphere™, RP-C18, 5 μm, 250 × 4.6 mm, Alltech, Deerfield, IL, USA). Silica gel 60 (230–400 mesh) was used for column chromatography. Pre-coated silica gel plates (Kieselgel 60 F254, 0.25 mm) were used for TLC analyses. Spots were visualized by heating after spraying with 10% H2SO4.
3
Isolation and Characterization of Amphidinium Species
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General Experimental Procedures The optical rotations and IR data were measured on a JASCO P-2300 polarimeter and a JASCO FT/IR-4100 spectrophotometer, respectively. The NMR data for 1 and 2 were recorded on an NMR400WB spectrometer (Agilent Technologies, U.S.A.) using 5.0 mm microcells (Shigemi Co., Ltd., Japan). The 1 H-NMR spectra of the products treated with NaIO 4 were measured on the same spectrometer equipped with a PFG-HX nanoprobe. All chemical shifts were reported in ppm relative to the residual proton and carbon signals of CDCl 3 (δ H 7.26 and δ C 77.16, respectively) and benzene-d 6 (C 6 D 6 , δ H 7.20 and δ C 128.0, respectively). ESI-MS was conducted on an LTQ Orbitrap XL spectrometer (ThermoFisher Scientific Inc., U.S.A.) The cytotoxic assay and the cultivation/harvest protocol was carried out using a literature procedure. 6) (link) Materials The dinoflagellate Amphidinium species (strain KCA09057) was monoclonally separated from benthic sea sands collected off Iriomote Island, Japan in May 2009. 6) (link) The voucher specimen was deposited at the Center for Advanced Marine Core Research, Kochi University.
4
Analytical Characterization of Compounds
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Optical rotations were measured on a JASCO P-2300 polarimeter (Tokyo, Japan).1H (500 MHz), and 13C NMR (125 MHz) spectra were recorded on a Bruker 500 NMR spectrometer (USA). The chemical shifts were given in δ (ppm), and coupling constants were reported in Hz. HR-MS spectra were obtained on a JEOL JMS-700 instrument (Tokyo, Japan). Column chromatography (CC) was carried out on polyamide 6L and Sephadex LH 20. Precoated silica gel plates (Merck, Kieselgel 60 F254, 0.25 mm, Merck, Darmstadt, Germany) and precoated RP-18 F254S plates (Merck, Darmstadt, Germany) were used for TLC analysis. A semi-preparative reversed-phase column (Supelco C18 column 250 × 10 mm, 5 μm) was used for HPLC.
5
Analytical Characterization of Organic Compounds
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For optical rotation the JASCO P-2300 polarimeter (JASCO, Tokyo, Japan) was used; for IR spectra, the Shimazu FTIR-8400S instrument (Shimazu, Columbia, MD 21046, USA) was used. A Bruker 600 or 500 Hz NMR spectrometer was used to record 1D and 2D NMR spectra (Bruker, MA, USA). A JEOL JMS-700 equipment was used to obtain HR-MS spectra (Tokyo, Japan). TLC analysis was conducted with precoated silica gel plates (Merck, Kieselgel60 F254, 0.25 mm, Merck, Darmstadt, Germany); chromatography (CC) was conducted with silica gel 60 (Merck, 230–400 mesh, Merck, Darmstadt, Germany). HPLC was carried out with a Jasco PU-980 pump, a Jasco UV-970 intelligent UV detector at 210 nm, and a semi-preparative reversed-phase column (Cosmosil C18, column 250 × 10 mm, 5 μm, Nacalai Tesque, Kyoto, Japan).
6
Spectroscopic Characterization of Organic Compounds
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A JASCO P-2300 polarimeter was used to measureoptical rotation (Jasco Corporation, Tokyo, Japan). A Shimazi FTIR-8400S was used to measure IR spectra (Columbia, MD 21046, USA). A Bruker 600 or 500 Hz NMR spectrometer was used to record 1D and 2D NMR spectra (MA, USA). Chemical shifts were expressed in parts per million (ppm), while coupling constants were expressed in hertz (Hz). On a JEOL JMS-700 instrument, HR-MS spectra were collected (Tokyo, Japan). A JASCO 810 polarimeter was used to measure electronic circular dichroism (ECD). For column chromatography, Merck’s Silica Gel 60 (230–400 mesh, Merck, Darmstadt, Germany) was employed. TLC examination was performed on precoated silica gel plates (Merck, Kieselgel 60 F254, 0.25 mm, Merck, Darmstadt, Germany). A Jasco PU-980 pump clever HPLC pump was used to perform high-performance liquid chromatography (HPLC).
7
Analytical Characterization of Compounds
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All reactions were monitored with thin layer chromatography carried out on 0.25 mm Merck silica gel plates (60 F 254 ) and a Shimadzu GC-14B gas chromatography (Kyoto, Japan) with a flame ionization detector equipped with a In-ertCap TC-1 column (0.25 mm i.d.×60 m×0.25 μm, GL Sciences, Tokyo, Japan) . The column temperature was programmed from 60℃ to 300℃ (5 min) at a rate of 10℃ / min. The injection and detection temperature were 300℃. Nitrogen was the carrier gas at a flow rate of 120 kPa. Infrared (IR) spectra were measured with a Thermo Fisher Scientific Nicolet iN10 spectrometer. Nuclear magnetic resonance (NMR) spectra were recorded on Bruker AVANCE 400 spectrometer at 400 MHz for 1 H and 100 MHz for 13 C. Chemical shifts were determined by using tetramethylsilane or the residual solvent peak in CDCl 3 (δ 7.26) for 1 H and the peak for CDCl 3 (δ 77.0) for 13 C as the internal references, respectively. The optical rotation of chiral compounds was measured with a JASCO (Tokyo, Japan) P 2300 polarimeter.
8
Characterization of Chiral Compounds
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All reactions were monitored using thin-layer chromatography carried out on 0.25 mm E. Merck silica gel plates (60 F254) . Infrared spectra were measured with a Thermo Fisher Scientific Nicolet iN10 spectrometer. Nuclear magnetic resonance spectra were recorded on Bruker AVANCE 400 spectrometer at 400 MHz for 1 H and 100 MHz for 13 C. Chemical shifts were determined by using tetramethylsilane or the residual solvent peak in CDCl 3 (δ 7.26) for 1 H and the peak for CDCl 3 (δ 77.0) for 13 C as the internal references, respectively. The optical rotation of chiral compounds was measured with a JASCO (Tokyo, Japan) P-2300 polarimeter.
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