Deuterium labeling of dopaquine

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The possibility of introducing deuterium into dopaquine, a compound consisting of quinone and dopamine fragments, has been studied. It has been established that isotope exchange can be carried out with deuterated water in the presence of trifluoroacetic acid (TFA) and HCl. Optimal conditions are the use of TFA at a temperature of 80°С. To activate isotope exchange, catalysts based on iridium or palladium (5%Pd/Al2O3, cycloocta-1,5-dienylyridium(I) 1,1,1,5,5,5-hexafluoropentane-2,4-dionate) were added to the reaction mixture in addition to the acid component. The preparative synthesis of [D]dopaquine was carried out by isotope exchange with deuterated water (D2O : TFA 5 : 1, 80°С, 3 h). [D]Dopaquine was obtained in 20% yield of with the deuterium content in the interval 1.2–1.4 atoms per molecule. The deuterium content in the dopamine fragment is 1.2–1.3 atoms per molecule. The quinone fragment contained approximately 4–7% of the isotope.

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Sobre autores

V. Shevchenko

National Research Centre Kurchatov Institute

Email: nagaev.img@yandex.ru
Rússia, Moscow

I. Nagaev

National Research Centre Kurchatov Institute

Autor responsável pela correspondência
Email: nagaev.img@yandex.ru
Rússia, Moscow

K. Shevchenko

National Research Centre Kurchatov Institute

Email: nagaev.img@yandex.ru
Rússia, Moscow

N. Myasoedov

National Research Centre Kurchatov Institute

Email: nagaev.img@yandex.ru
Rússia, Moscow

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2. Fig. 1. Isotopomeric composition of dopaquine depending on temperature (a, b, d), D2O : TFA ratio (a, c) and reaction time (b, d, f). a – 70°C, 3 h, D2O : TFA 5 : 1; b – 80°C, 3 h, D2O : TFA 5 : 1; c – 70°C, 3 h, D2O : TFA 1 : 1; d – 90°C, 3 h, D2O : TFA 5 : 1; d – 80°C, 0.5 h, D2O : TFA 5 : 1; f – 80°C, 1 h, D2O : TFA 5 : 1.

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3. Fig. 2. Isotopomer spectrum upon introduction of deuterium into dopaquine (80°C, D2O : TFA 5 : 1): a – without catalyst; b – in the presence of CODIrF6Acac; c – in the presence of 5% Pd/Al2O3–Al2O3.

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4. Fig. 3. Analysis of the reaction mixture on a Milichrom A-02 chromatograph (the first peak indicated is the retention time of dopamine, the second is dopaquine).

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5. Scheme 1

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6. Scheme 2

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