2023•Доклады Российской академии наук Науки о жизниRequires access

SYNTHESIS OF DEUTERIUM-LABELED PYRROLYLCARNOSINE

Valery P. Shevchenko, Igor Yu Nagaev, Т. Н. Федорова, Nikolai F. Myasoedov

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Abstract

The effect of temperature on the effectiveness of the introduction of deuterium into pyrrolylcarnosine (PC) has been studied. Deuterium gas and heavy water were used as a source of deuterium. Isotope exchange was carried out using solid-phase and liquid-phase methods. It was found that it is better to use isotope exchange with deuterated water to obtain preparative amounts of labeled pyrrolylcarnosine. When using the solid-phase method, the main label is in pyrrole. The inclusion of deuterium at a higher temperature occurs more evenly. In addition, the use of deuterated water made it possible to reduce the amount of unlabeled isotopomer to almost 0%, obtain a product with a yield of 70% and a content of more than 7 deuterium atoms. It is established that the content of deuterium in the substance can be increased by pretreating the reaction mixture with deuterium gas. This approach opens up additional opportunities for synthesis of labeled compounds.

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The effect of temperature on the effectiveness of the introduction of deuterium into pyrrolylcarnosine (PC) has been studied. Deuterium gas and heavy water were used as a source of deuterium. Isotope exchange was carried out using solid-phase and liquid-phase methods. It was found that it is better to use isotope exchange with deuterated water to obtain preparative amounts of labeled pyrrolylcarnosine. When using the solid-phase method, the main label is in pyrrole. The inclusion of deuterium at a higher temperature occurs more evenly. In addition, the use of deuterated water made it possible to reduce the amount of unlabeled isotopomer to almost 0%, obtain a product with a yield of 70% and a content of more than 7 deuterium atoms. It is established that the content of deuterium in the substance can be increased by pretreating the reaction mixture with deuterium gas. This approach opens up additional opportunities for synthesis of labeled compounds.

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Available abstract

The effect of temperature on the effectiveness of the introduction of deuterium into pyrrolylcarnosine (PC) has been studied. Deuterium gas and heavy water were used as a source of deuterium. Isotope exchange was carried out using solid-phase and liquid-phase methods. It was found that it is better to use isotope exchange with deuterated water to obtain preparative amounts of labeled pyrrolylcarnosine. When using the solid-phase method, the main label is in pyrrole. The inclusion of deuterium at a higher temperature occurs more evenly. In addition, the use of deuterated water made it possible to reduce the amount of unlabeled isotopomer to almost 0%, obtain a product with a yield of 70% and a content of more than 7 deuterium atoms. It is established that the content of deuterium in the substance can be increased by pretreating the reaction mixture with deuterium gas. This approach opens up additional opportunities for synthesis of labeled compounds.

Key concepts: Deuterium, Chemistry, Isotope, Yield (engineering), Heavy water, Isotopomers, Hydrogen–deuterium exchange, Deuterium NMR

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