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A method for introducing deuterium in organic matter
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An organic, deuterated technology, applied in organic chemistry methods, preparation of organic compounds, introduction of isotopes into organic compounds, etc., to achieve the effects of good selectivity, mild reaction conditions and a wide range of substrates
Active Publication Date: 2022-01-18
湖州中科颐格生物科技有限公司
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[0014] However, selective introduction of deuterium at specific positions in the carbon chain remains challenging
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Embodiment 1
[0044]
[0045] Follow general protocol using 0.75 mmol substrate, DTBP (1.2 equiv.), Ph 2 POEt (2.0equiv.), the reaction solvent is a mixed solvent of dichloromethane and deuterium water (6ml, V:V=2:1). After the reaction was completed, the solvent was evaporated under reduced pressure, and the crude product was separated by a chromatographic column (100% petroleumether) to obtain 100.1 mg of colorless liquid, which was the product, with a yield of 89% and a deuteration rate of 90%. NMR and mass spectrometry data: 1 H NMR (400 MHz, CDCl 3 ) δ 7.28 (d, J = 7.9 Hz, 2H), 7.11(d, J = 7.9 Hz, 2H), 2.37 – 2.28 (m, 2H), 1.30 (s, 9H). 13 C NMR (101 MHz, CDCl 3 ) δ 148.17, 134.84, 128.79, 125.19, 34.35, 31.48, 20.62 (t, J = 19.3Hz).GC-MS (EI): m / z = 149.14.
Embodiment 2
[0047]
[0048] Follow the general protocol using 0.75 mmol of substrate, dicumyl peroxide (DCP) (1.2 equiv.), Ph 2 POEt (2.0 equiv.), the reaction solvent is a mixed solvent of dichloromethane and deuterium water (6ml, V:V=2:1). After the reaction, the solvent was evaporated under reduced pressure, and the crude product was separated by a chromatographic column (petroleumether / ethyl acetate=8:1) to obtain 214.8 mg of white solid, which was the product. The yield was 96% and the deuteration rate was 97%. NMR and mass spectrometry data: 11 H NMR (400 MHz, CDCl 3 ) δ 7.42 – 7.22(m, 10H), 5.12 (s, 4H), 2.70 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 172.03,135.72, 128.55, 128.26, 128.22, 66.56, 29.10.HRMS (ESI) calcd for C 18 H 17 DO 4 [M+ Na] + m / z = 322.1160, found: 322.1167.
Embodiment 3
[0050]
[0051] Glutathione ((0.0738 g, 80 mM)) was dissolved in 3 ml of deuterium water, TPPTS (0.2728 g, 160 mM, 2.0 equiv.) and DTBP (0.0702 g, 160 mM, 2.0 equiv.) were sequentially added to the reaction system. The reaction system was reacted at room temperature for 6 h under the irradiation of 36 W fluorescent lamp. After NMR and mass spectrometry analysis, the reaction was successful, the yield was >95%, and the deuteration rate was 98%. NMR and mass spectrometry data: 1 H NMR (400 MHz, D 2 O) δ 4.15 (t, J = 7.2 Hz, 1H), 3.79 (s, 2H), 3.72 (t, J = 6.3 Hz, 2H), 2.36 (t, J = 7.2, 2H), 2.02 (dt, J = 7.2, 6.3Hz, 2H), 1.17 (d, J = 7.2 Hz, 2H).ESI-MS calcd for 6a C 10 H 16 DN 3 O 6 [M+Na] + m / z =299.1072, found:299.1023.
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Abstract
The invention relates to a method for introducing deuterium in organic matter, in particular to a method for introducing deuterium in organic compounds containing mercapto or disulfide bonds. It belongs to the technical field of molecular markers. The invention discloses a method for introducing deuterium into organic matter. The organic matter is dissolved in a mixed solvent of organic solvent and deuterium water, then a phosphinereagent and a free radical initiator are added, and the reaction is carried out under light conditions for 3-6 hours, and the end The organic substance is converted into the corresponding deuterated product; the organic substance is a mercaptan, a disulfide or a polypeptide organic compound containing cysteine. The method for introducing deuterium in the present invention has the characteristics of high deuterium efficiency, good selectivity, good functional group tolerance, high yield, mild reaction conditions, no need for metals to participate in the reaction, and a wide range of substrates. It is especially suitable for specific positions in the carbon chain. Selective introduction of deuterium. At the same time, this method can also be applied to polypeptide substrates.
Description
technical field [0001] The present invention relates to a method for introducing deuterium in organic matter, in particular to a method for introducing deuterium into organic compounds containing sulfhydryl groups or disulfide bonds. It belongs to the field of molecular marker technology. Background technique [0002] As an important labeling method, deuterium has important applications in drugmetabolism, new reaction mechanism research, nuclear magnetic resonance, mass spectrometry and other research. 1-10 . The introduction of deuterium at the appropriate position of the drug molecule can greatly alter the metabolism and pharmacokinetic properties of the drug. In 2017, the FDA approved the first deuterated drug, deutetrabenazine, which greatly promoted the research of deuterated drugs and the development of deuterated methods. 11 . [0003] 1. Helfenbein, J. et al. Isotopic effect study of propofol deuteration on the metabolism, activity, and toxicity of the anesthe...
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