Synthesis of Phosphinic Pseudomethionyl-Glutamyl-Histidine

The amidoalkylation of a phosphonous acid containing a structural isostere of diethyl glutamiate, using ethyl carbamate and 3-(methylthio)propionaldehyde, was proposed for the synthesis of NC(O)OEt-protected phosphinic pseudo-Met-Glu-peptide. Subsequent adamantyl protection of the phosphorylic funct...

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Bibliographic Details
Published inRussian journal of general chemistry Vol. 93; no. 8; pp. 2022 - 2028
Main Authors Dmitriev, M. E., Shevchenko, K. V., Shevchenko, V. P., Nagaev, I. Yu, Kalashnikova, I. P., Ragulin, V. V., Myasoedov, N. F.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 01.08.2023
Springer Nature
Springer
Springer Nature B.V
Subjects
Amino acids
Carbamates
Chemistry
Chemistry and Materials Science
Chemistry, Multidisciplinary
Chemistry/Food Science
Ethyl carbamate
Glutamate
Histidine
Hydrolysis
Peptides
Physical Sciences
Science & Technology
Synthesis
cyclic anhydride
amidoalkylation
pseudomethionyl-glutamyl-histidine
phosphinic peptides
PEPTIDES
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Summary:The amidoalkylation of a phosphonous acid containing a structural isostere of diethyl glutamiate, using ethyl carbamate and 3-(methylthio)propionaldehyde, was proposed for the synthesis of NC(O)OEt-protected phosphinic pseudo-Met-Glu-peptide. Subsequent adamantyl protection of the phosphorylic function and hydrolysis of carboxylic groups made it possible to obtain phosphinic Met-[P]-Glu peptide 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.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363223080108