Synthesis of phosphinic pseudomethionyl-glutamyl-histidine

Мұқаба

Дәйексөз келтіру

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Рұқсат жабық Рұқсат ақылы немесе тек жазылушылар үшін

Аннотация

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.

Авторлар туралы

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”

Әдебиет тізімі

  1. Шевченко К.В., Нагаев И.Ю., Андреева Л.А., Шевченко В.П., Мясоедов Н.Ф. // Докл. АН. 2013. Т. 449. № 6. С. 733
  2. Shevchenko K.V., Nagaev I.Yu., Andreeva L.A., Shevchenko V.P., Myasoedov N.F. // Doklady Biol. Sci. 2013. Vol. 449. N 1. P. 110. doi: 10.1134/S0012496613020166
  3. Vinyukov A.V., Dmitriev M.E.,Andreeva L.A., Ustyugov A.A., Shevchenko V.P., Sidoruk K.N., Lednev B.V., Freyman V.M., Dobrovolskiy Y.A., Ragulin V.V., Myasoedov N.F. // Biochem. Biophys. Res. Commun. 2021. Vol. 539. P. 15. doi: 10.1016/j.bbrc.2020.12.087
  4. Collinsova M., Jiracek J. // Curr. Med. Chem. 2000. Vol. 7. N 6. P. 629. doi: 10.2174/0929867003374831
  5. Dive V., Georgiadis D., Matziari M., Makaritis A., Beau F., Cuniasse P., Yiotakis A. // Cell. Mol. Life Sci. 2004. Vol. 61. P. 2010. doi: 10.1007/s00018-004-4050-y
  6. Mucha A. // Molecules. 2012. Vol. 17. N 11. P. 13530. doi: 10.3390/molecules171113530
  7. Georgiadis D., Dive V. // Top. Curr. Chem. 2015. Vol. 360. P. 1. doi: 10.1007/128_2014_571
  8. Zinc Metalloproteases in Health and Disease / Ed. N.M. Hooper. London: Taylor and Francis, 1996. P. 153.
  9. Hori M., Nishida K. // Cardiovasc. Res. 2009. Vol. 81. N 3. P. 457. doi: 10.1093/cvr/cvn335
  10. Whittaker M., Ayscough A. // Celltransmissions. 2001. Vol. 17. N 1. P. 3.
  11. Pirad B., Matter H. // J. Med. Chem. 2006. Vol. 49. N 1. P. 51. doi: 10.1021/jm050363f
  12. Dmitriev M.E., Ragulin V.V. // Tetrahedron Lett. 2010. Vol. 51. N. 19. P. 2613. doi: 10.1016/j.tetlet.2010.03.020
  13. Dmitriev M.E., Ragulin V.V. // Tetrahedron Lett. 2012. Vol. 53. N. 13. P. 1634. doi: 10.1016/j.tetlet.2012.01.094
  14. Dmitriev M.E., Golovash S.R., Borodachev A.V., Ragulin V.V. // J. Org. Chem. 2021. Vol. 86. N 1. P. 593. doi: 10.1021/acs.joc.0c02259
  15. Дмитриев М.Э., Винюков А.В., Рагулин В.В., Мясоедов Н.Ф. // ЖОХ. 2015. Т. 85. Вып. 9. С. 1576
  16. Dmitriev M.E., Vinyukov A.V., Ragulin V.V., Myasoedov N.F. // Russ. J. Gen. Chem. 2015. Vol. 85. N 9. P. 2215. doi: 10.1134/S1070363215090315
  17. Yiotakis A., Vassiliou S., Jiracek J., Dive V. // J. Org. Chem. 1996. Vol. 61. N 19. P. 6601. doi: 10.1021/jo9603439
  18. Georgiadis D., Dive V., Yiotakis A. // J. Org. Chem. 2001. Vol. 66. N 20. P. 6604. doi: 10.1021/jo0156363
  19. Kalyanam N., Majeed M. // Chim. Oggi. 2008. Vol. 26. N 3. P. 44.
  20. Amino Y., Nakazawa M., Kaneko M., Miyaki T., Miyamura N., Maruyama Y., Eto Y. // Chem. Pharm. Bull.. 2016. Vol. 64. N 8. P. 1181. doi: 10.1248/cpb.c16-00293

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