Synthesis of phosphinic structural analogue of Met-Glu-His-Phe

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Abstract

The synthesis of a phosphinic structural analogue of the tetrapeptide Met-Glu-γ-His-Phe by adding the dipeptide component His-Phe to the adamantyl ester of the phosphinic pseudo-Met-[P]-Glu-peptide in the form of cyclic glutamate anhydride is proposed. The conditions for the interaction of phosphinic pseudo-Met-[P]-Glu-anhydride with His-Phe in free form to form phosphinic Met-[P]-Glu-γ-His-Phe tetrapeptide have been found. A chromatographic mass-spectrometry study, including MS2, and NMR of the phosphinic tetrapeptide on 1H, 13C, 31P nuclei was carried out using the methods of two-dimensional 1H–1H COSY, 1H–13C HSQC and 1H–13C HMBC NMR spectroscopy.

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About the authors

V. P. Shevchenko

National Research Centre “Kurchatov Institute”

Author for correspondence.
Email: rvalery@dio.ru
Russian Federation, Moscow

А. V. Borodachev

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry of the Russian Academy of Sciences

Email: rvalery@dio.ru

Institute of Physiologically Active Compounds

Russian Federation, Chernogolovka, Moscow

М. E. Dmitriev

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry of the Russian Academy of Sciences

Email: rvalery@dio.ru

Institute of Physiologically Active Compounds

Russian Federation, Chernogolovka, Moscow

К. V. Shevchenko

National Research Centre “Kurchatov Institute”

Email: rvalery@dio.ru
Russian Federation, Moscow

I. P. Kalashnikova

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry of the Russian Academy of Sciences

Email: rvalery@dio.ru

Institute of Physiologically Active Compounds

Russian Federation, Chernogolovka, Moscow

А. N. Ivanov

University “Synergy”

Email: rvalery@dio.ru
Russian Federation, Moscow

I. Yu. Nagaev

National Research Centre “Kurchatov Institute”

Email: rvalery@dio.ru
Russian Federation, Moscow

V. V. Ragulin

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry of the Russian Academy of Sciences

Email: rvalery@dio.ru

Institute of Physiologically Active Compounds

Russian Federation, Chernogolovka, Moscow

N. F. Myasoedov

National Research Centre “Kurchatov Institute”

Email: rvalery@dio.ru
Russian Federation, Moscow

References

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Supplementary files

Supplementary Files
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1. JATS XML
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2. Fig.1. 31P{1H} NMR spectra (202.48 MHz) of tetrapeptide 1 in CDCl3 (1), acetone-d6 (2), acetone-d6–D2O mixture (8:2, vol.) (3).

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3. Fig.2. 1H NMR spectra (500.2 MHz) of tetrapeptide 1 in CDCl3 (1), acetone-d6 (2), acetone-d6–D2O mixture (8:2, vol.) (3).

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4. Fig.3. 1H NMR spectrum (500.2 MHz) of tetrapeptide 1 in a mixture of acetone-d6–D2O (8:2, vol.).

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5. Fig.4. Fragment of the 1H NMR spectrum (500.2 MHz) of tetrapeptide 1 in a mixture of acetone-d6–D2O (8:2, vol.). Signals of histidine are marked in green, phenylalanine in blue, pseudoglutamine in red, and pseudomethionine in lilac.

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6. Fig.5. Fragment of the 1H NMR spectrum (500.2 MHz) of tetrapeptide 1 in acetone-d6 (region of NH and CH= protons).

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7. Fig.6. 13С{1H} NMR spectrum (125.79 MHz) of tetrapeptide 1 in a mixture of acetone-d6–D2O (8:2, vol).

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8. Fig.7. Fragment of the 13C{1H} NMR spectrum (125.79 MHz) of tetrapeptide 1 in a mixture of acetone-d6–D2O (8:2, vol.). The region of carboxyl and amide carbons is shown. The complexity of the signals is due to different diastereomeric and conformer forms.

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9. Fig.8. Fragment of the 13C{1H} NMR spectrum (125.79 MHz) of tetrapeptide 1 in a mixture of acetone-d6–D2O (8:2, vol.). The region of aromatic carbons is given.

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10. Fig.9. 1H–1H COSY NMR spectrum (500.2 MHz) of tetrapeptide 1 in a mixture of acetone-d6–D2O (8:2, vol.).

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11. Fig. 10. 1H–1H COSY NMR spectrum (500.2 MHz) of tetrapeptide 1 in acetone-d6. The area of NH group signals is shown.

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12. Fig. 11. 1H–13C HSQC NMR spectrum of tetrapeptide 1 in a mixture of acetone-d6–D2O (8:2, vol).

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13. Fig. 12. 1H–13C NMR spectrum of HMBC tetrapeptide 1 in a mixture of acetone-d6–D2O (8:2, v/v).

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14. Scheme 1.

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15. Scheme 2.

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16. Scheme 3.

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