Synthesis of Deuterium-Labelled Salicylcarnosine

Effect of temperature on the efficiency of deuterium introduction into a new biologically active compound salicylcarnosine (SC) has been studied. Gaseous deuterium and heavy water were used as deuterium sources. The synthesis of labelled SC by a solid-phase method at 190°C leads to formation of [D]S...

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Published inDoklady. Chemistry Vol. 511; no. 1; pp. 181 - 185
Main Authors Shevchenko, V. P., Nagaev, I. Yu, Kulikova, O. I., Myasoedov, N. F.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 01.07.2023
Springer Nature B.V
Subjects
Ambient temperature
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Deuterium
Heavy water
Industrial Chemistry/Chemical Engineering
Peptides
Solid phases
Temperature effects
synthesis
salicylcarnosine
labelled compounds
deuterium
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Summary:Effect of temperature on the efficiency of deuterium introduction into a new biologically active compound salicylcarnosine (SC) has been studied. Gaseous deuterium and heavy water were used as deuterium sources. The synthesis of labelled SC by a solid-phase method at 190°C leads to formation of [D]SC in 53% yield and deuterium content about 4.8 atoms per molecule. It has been shown that isotope exchange between SC protons and deuterium water proceeds more efficiently after preliminary treatment of catalyst with gaseous deuterium at ambient temperature. [D]SC forms in 46% yield and contains about 7.3 deuterium atoms per molecule. The preparative synthesis of labelled SC by this procedure at 190°C results in [D]SC yield of 60–70% at deuterium content about 6.2 atoms per molecule. The new procedure for the activation of deuterium inclusion in peptides opens additional opportunities for preparing highly labelled compounds.
ISSN:0012-5008
1608-3113
DOI:10.1134/S0012500823600542