Synthesis of P,N-protected phosphinic pseudoprolylglycine block
- Authors: Vinyukov A.V.1, Dmitriev M.E.1, Afanas’ev A.V.2, Ragulin V.V.1, Andreeva L.A.3, Myasoedov N.F.3
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Affiliations:
- Institute of Physiologically Active Compounds
- Chembridge Ltd.
- Institute of Molecular Genetics
- Issue: Vol 87, No 2 (2017)
- Pages: 266-269
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/218302
- DOI: https://doi.org/10.1134/S1070363217020189
- ID: 218302
Cite item
Abstract
The phosphine block N-Cbz-Pro-ψ[P(O)(OAd)CH2]-GlyOH has been synthesized for subsequent peptide assembly. A procedure has been proposed for the preparation of phosphorus prolylglycine isostere by three-center two-component amide version of the Kabachnik–Fields reaction. A combination of amide and carbonyl fragments in the molecule of 4-N-Cbz-aminobutyraldehyde makes it possible to accomplish cyclization with generation in situ of a cyclic pyrrolidine Schiff base, followed by Arbuzov phosphorylation of the latter with diacetyl 2-(ethoxycarbonyl)ethyl phosphonite generated in situ.
About the authors
A. V. Vinyukov
Institute of Physiologically Active Compounds
Email: rvalery@dio.ru
Russian Federation, Severnyi proezd 1, Chernogolovka, Moscow oblast, 142432
M. E. Dmitriev
Institute of Physiologically Active Compounds
Email: rvalery@dio.ru
Russian Federation, Severnyi proezd 1, Chernogolovka, Moscow oblast, 142432
A. V. Afanas’ev
Chembridge Ltd.
Email: rvalery@dio.ru
Russian Federation, Pirogovskaya ul. 1, str. 5, Moscow, 119435
V. V. Ragulin
Institute of Physiologically Active Compounds
Author for correspondence.
Email: rvalery@dio.ru
Russian Federation, Severnyi proezd 1, Chernogolovka, Moscow oblast, 142432
L. A. Andreeva
Institute of Molecular Genetics
Email: rvalery@dio.ru
Russian Federation, pl. Akademika Kurchatova 2, Moscow, 123182
N. F. Myasoedov
Institute of Molecular Genetics
Email: rvalery@dio.ru
Russian Federation, pl. Akademika Kurchatova 2, Moscow, 123182
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