Synthesis of phosphinic pseudomethionyl-glutamyl-histidine

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Abstract

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.

About the authors

M. E Dmitriev

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

K. V Shevchenko

National Research Centre “Kurchatov Institute”

V. P Shevchenko

National Research Centre “Kurchatov Institute”

I. Yu. Nagaev

National Research Centre “Kurchatov Institute”

I. P Kalashnikova

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

V. 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. F Myasoedov

National Research Centre “Kurchatov Institute”

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