Effect of temperature during preactivation of 5% Pd/C and 5% Pd/Al2O3 with deuterium gas on isotope exchange between deuterium water and an organic compound

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Abstract

It was demonstrated by the example of serotonin, 3-(N-pyrrolyl)propanoyl-L-histidine, sodium p-phenylbenzoate, and Pro–Gly–Pro that activation of isotope exchange with D2O also occurred when a solution of an organic compound in D2O was mixed with 5% Pd/Al2O3 or 5% Pd/С (after preliminary treatment of catalysts with deuterium gas on heating). When implementing this technique, 2–3 atoms of deuterium were incorporated in serotonin, 4–5 atoms, in Pro–Gly–Pro, 7–8 atoms, in 3-(N-pyrrolyl)propanoyl-L-histidine, and 3–4 atoms, in sodium p-phenylbenzoate. In the latter case, as judged from the composition of the reaction products, atomic deuterium takes part in the activation of isotope exchange with D2O. The participation of atomic deuterium in these reactions follows from the intensification of the degradation of the compounds during deuteration. When using compounds that do not contain labile fragments, isotope exchange with D2O can be activated by keeping the catalyst at room temperature and heating.

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V. P. Shevchenko

National Research Centre Kurchatov Institute

Author for correspondence.
Email: nagaev.img@yandex.ru
Russian Federation, pl. Kurchatova 2, Moscow, 123182

I. Yu. Nagaev

National Research Centre Kurchatov Institute

Email: nagaev.img@yandex.ru
Russian Federation, pl. Kurchatova 2, Moscow, 123182

K. V. Shevchenko

National Research Centre Kurchatov Institute

Email: nagaev.img@yandex.ru
Russian Federation, pl. Kurchatova 2, Moscow, 123182

L. A. Andreeva

National Research Centre Kurchatov Institute

Email: nagaev.img@yandex.ru
Russian Federation, pl. Kurchatova 2, Moscow, 123182

N. F. Myasoedov

National Research Centre Kurchatov Institute

Email: nagaev.img@yandex.ru
Russian Federation, pl. Kurchatova 2, Moscow, 123182

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Supplementary files

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2. Fig. 1. Isotopic composition of PPG after reaction with D2O (150°C, 30 min) with catalysts activated at room temperature. a – previous method, 5% Pd/Al2O3; b – new method, 5% Pd/Al2O3; c – new method, 5% Pd/C

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3. Fig. 2. Isotopic composition of PPG after reaction with D2O (150°C, 30 min) with catalysts activated at 180 and 200°C. a – 180°C, 5% Pd/C; b – 180°C, 5% Pd/Al2O3; c – 200°C, 5% Pd/C; d – 200°C, 5% Pd/Al2O3.

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4. Fig. 3. Isotopic composition of serotonin after reaction with D2O (200°C, 30 min): a – 5% Pd/Al2O3–Al2O3–serotonin (5:20:1) mixture, activated at room temperature for 60 min (previous method); b – 5% Pd/Al2O3, activated at 200°C for 10 min followed by vacuumization (new method).

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5. Fig. 4. Isotopic composition of serotonin after reaction with D2O (150°C, 30 min, new method): a – 5% Pd/Al2O3, activated at 180°C for 10 min followed by vacuum; b – 5% Pd/Al2O3, activated at 180°C for 10 min without vacuum.

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6. Fig. 5. Isotopic composition of Pro–Gly–Pro after reaction with D2O (150°C, 30 min): a – Peptide–5% Pd/Al2O3–Al2O3, D2, 1 h, room temperature (previous method); b – 5% Pd/Al2O3–Al2O3, D2, 1 h, room temperature, then the peptide was added to D2O; c – 5% Pd/Al2O3, D2, 1 h, room temperature, then the peptide was added to D2O.

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7. Fig. 6. Isotopic composition of Pro–Gly–Pro after reaction with D2O (150°C, 30 min): a – 5% Pd/Al2O3, D2, 10 min, 200°C, then addition of the peptide to D2O; b – 5% Pd/Al2O3–Al2O3, D2, 10 min, 200°C, then addition of the peptide to D2O; c – 5% Pd/Al2O3, D2, 10 min, 200°C, then vacuum, then addition of the peptide to D2O

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8. Fig. 7. Isotopic composition of Pro–Gly–Pro fragments after reaction with D2O: a, g – deuterium in the C-terminal proline; b, d – deuterium in the Gly–Pro fragment; c, e – deuterium in the Pro–Gly fragment. Reaction conditions: a–c – 5% Pd/Al2O3, D2, 10 min, 200°C, then peptide in D2O, 150°C, 30 min; g–e – mixture of 5% Pd/Al2O3–Al2O3–peptide, D2, 1 hour, room temperature, then 150°C, D2O, 30 min.

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9. scheme 1

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10. scheme 2

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