Synthesis of phosphinic pseudomethionyl-glutamyl-histidine

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Resumo

The amidoalkylation reaction of a phosphonous acid containing a structural isostere of diethyl glutamiate using ethyl carbamate and 3-(methylthio)propionaldehyde was proposed for the synthesis of phosphinic pseudo-NC(O) OEt-protected Met-Glu-peptide. Subsequent adamantyl protection of the phosphorylic function and hydrolysis of carboxylic groups made it possible to obtain phosphinic pseudo-Met-[P]-Glu in the form of cyclic glutamate anhydride. It was found that the latter reacts with the third amino acid component histidine to form the phosphinic Met-[P]-Glu-γ-His tripeptide.

Sobre autores

M. Dmitriev

Institute of Physiologically Active Compounds at Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences

K. Shevchenko

National Research Centre “Kurchatov Institute”

V. Shevchenko

National Research Centre “Kurchatov Institute”

I. Nagaev

National Research Centre “Kurchatov Institute”

I. Kalashnikova

Institute of Physiologically Active Compounds at Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences

V. Ragulin

Institute of Physiologically Active Compounds at Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences

Email: rvalery@dio.ru

N. Myasoedov

National Research Centre “Kurchatov Institute”

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