Microbial 1,2-dehydrogenation of 6 Alpha-Methylhydrocortisone 11-trifluoroacetate

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

Transformation of 11-trifluoroacetate 6α-methylhydrocortisone (11-TFA MHC) by cells of actinobacteria Arthrobacter (Nocardioides) was carried out in the presence of α-cyclodextrin (α-CD). The composition and dynamics of the transformation products accumulation in the culture medium at various pH values and the ratio of α-CD/substrate were studied. It was shown that the addition of α-CD to the transformation medium at pH less than 7 promotes an increase in the rate of 1,2-dehydrogenation with the formation of 6 α-methylprednisolone 11-trifluoroacetate (11-TFA MPL). At pH over 7, the primary process is the hydrolysis of the 11β-trifluoroacetyloxy group. In this case, the participation of α-CD in these processes as an acceptor of the trifluoroacetyl ion is not excluded.

About the authors

T. S. Savinova

Erisman FSCH of Rospotrebnadzor

Author for correspondence.
Email: tatiana_savinova@rambler.ru
Russia, 141014, Mytishchi

A. Yu. Arinbasarova

Skryabin Institute of Biochemistry and Physiology of Microorganisms, Federal Research Center “Pushchino Scientific Center for Biological Research of the Russian Academy of Science”

Email: tatiana_savinova@rambler.ru
Russia, 142290, Pushchino

A. V. Kazantsev

Lomonosov Moscow State University, Faculty of Chemistry

Email: tatiana_savinova@rambler.ru
Russia, 119991, Moscow

O. S. Savinova

Bach Institute of Biochemistry, Biotechnology Research Center of Russian Academy of Sciences

Email: tatiana_savinova@rambler.ru
Russia, 119071, Moscow

N. V. Lukashev

Lomonosov Moscow State University, Faculty of Chemistry

Email: tatiana_savinova@rambler.ru
Russia, 119991, Moscow

References

  1. Annen K., Petzoldt K., Laurent H., Wiechert R., Hofmeister H. // Патент США. 1990. № 4912098.
  2. Kominek L.A., Wolf H.J. // Патент США. 1987. № 4704358.
  3. Аринбасарова А.Ю., Кощеенко К.А., Андрюшина В.А., Гриненко Г.С., Скрябин Г.К. // Патент РФ. 1995. № 1830949.
  4. Arinbasarova A.Yu., Karpov A.V., Fokina V.V., Medentsev A.G., Koshcheyenko K.A. // Enzym. Microb. Tech. 1996. V. 19. № 7. P. 501–506. https://doi.org/10.1016/S0141-0229(96)80001-C
  5. Pinheiro H.M., Cabral J.M.S. // Biotech. Bioeng. 1991. V. 37. № 2. P. 97–102. https://doi.org/10.1002/bit.260370202
  6. Santos R.A., Caldeira J.C.G., Pinheiro H.M. and Cabral J.M.S. // Biotech. Lett. 1991. V. 13. № 5. P. 349–354. https://doi.org/10.1007/BF01027681
  7. Fokina V.V., Sukhodolskaya G.V., Baskunov B.P., Turchin K.F., Grinenko G.S., Donova M.V. // Steroids. 2003. V. 68. № 5. P. 415–421. https://doi.org/10.1016/S0039-128X(03)00043-6
  8. Фокина В.В., Суходольская Г.В., Шутов А.А., Николаева В.М., Донова М.В., Савинова Т.С., Лукашев Н.В., Суровцев В.В. // Патент РФ. 2013. № 2480475.
  9. Донова М.В. // Биоконверсия стероидных соединений актинобактериями. Пущино: ОНТИ ПНЦ РАН, 2010. 196 c. ISBN 978-5-904385-12-5.
  10. Kominek L.A., Wolf H.J. // Патент США. 1985. № 4524134.
  11. Fokina V.V., Donova M.V. // J. Steroid Biochem. Mol. Biol. 2003. V. 87. № 4-5. P. 319–325. https://doi.org/10.1016/j.jsbmb.2003.10.002
  12. Annen K., Petzoldt K., Laurent H., Wiechert R., Hofmeister H., Wendt H. // Патент Чехословакии. 1986. № 244147.
  13. Annen K., Laurent H., Hofmeister H., Petzoldt K., Wiechert R. // Патент США. 1982. № 4330541.
  14. Annen K., Laurent H., Hofmeister H., Topert M. // Патент США. 1986. № 4619922.
  15. Андрюшина В.А., Стыценко Т.С., Савинова Т.С., Скрябин К.Г., Гриненко Г.С. // Хим.-фарм. журн. 2008. Т. 42. № 3. С. 32–39. https://doi.org/10.30906/0023-1134-2008-42-3-32-39
  16. Савинова Т.С., Казанцев А.В., Лукашёв Н.В., Аринбасарова А.Ю., Степанов А.И., Скрябин Г.А. // Патент РФ. 2008. № 2337918.
  17. Wang M., Zhang L., Shen Y., Ma Y., Zheng Y., Luo J.J. // Mol. Cat. B: Enzymatic. 2009. V. 59. № 1–3. P. 58–63. https://doi.org/10.1016/j.molcatb.2008.12.017
  18. Zhang L., Wang M., Shen Y., Ma Y., Luo J. // Appl. Biochem. Biotechnol. 2009. V. 159. № 3. P. 642–654. https://doi.org/10.1007/s12010-008-8499-2
  19. Hesselink P.G.M., van Vliet S., de Vries H., Hesselink B.W. // Enz. Microb. Technol. 1989. V. 11. № 7. P. 398–404. https://doi.org/10.1016/0141-0229(89)90133-6
  20. Udvardy N.E., Bartho I., Hantos G., Trinn M., Vida Z., Szejtli J., Stadler A., Habon I., Balazs M. // Патент США. 1985. № 4528271.
  21. Shtratnikova V.Yu, Schelkunov M.I., Fokina V.V., Bragin E.Y., Shutov A.A., Donova M.V. // BMC Biotechnology, 2021. V. 21. № 7. https://doi.org/10.1186/s12896-021-00668-9
  22. Rohman A., Dijkstra B.W. // Biotechnol. Adv. 2021. V. 49. 107751. https://doi.org/10.1016/j.biotechadv.2021.107751
  23. Савинова Т.С., Казанцев А.В., Лукашёв Н.В. // Патент РФ. 2018. № 2663484.
  24. Buhler D.R., Thomas R.C. Jr., Schlagel C.A. // Endocrinology. 1965. V. 76. № 5. P. 852–864. https://doi.org/10.1210/endo-76-5-852
  25. Fourmentin S., Crini G., Lichtfouse E. // Cyclodextrin-Steroid Interactions and Applications to Pharmaceuticals, Food, Biotechnology and Environment. Springer, 2018. P. 19–57. https://doi.org/10.1007/978-3-319-76162-6_2
  26. Donze C., Coleman A.W. // Inclusion Phenom. Mol. Recognit. Chem. 1993. V. 16. № 1. P. 1–15. https://doi.org/10.1007/bf00708758
  27. Thi T.D., Nauwelaerts K., Froeyen M., Baudemprez L., Van Speybroeck M., Augustijns P. et al. // J. Pharm. Sci. 2010. V. 99. P. 3863–3873. https://doi.org/10.1002/jps.22227
  28. Rinaldi L., Binello A., Stolle A., Curini M., Cravotto G. // Steroids. 2015. V. 98. P. 58–62. https://doi.org/10.1016/j.steroids.2015.02.016
  29. VanEtten R.L., Clowes G.A., Sebastian J.F., Bender M.L. // J. Am. Chem. Soc. 1967. P. 3253–3262.
  30. Fokina V.V., Karpov A.V., Sidorov I.A., Andrjushina V.A., Arinbasarova A.Y. // Appl. Microbiol. Biotechnol. 1997. V. 47. № 6. P. 645–649. https://doi.org/10.1007/s002530050989
  31. Arinbasarova A.Y., Medentsev A.G., Akimenko V.K., Koshcheenko K.A., Skryabin G.K. // J. Steroid Biochem. 1985. V. 23. № 3. P. 307–312. https://doi.org/10.1016/0022-4731(85)90409-1
  32. Безбородов А.М., Загустина Н.А. // Прикл. биохимия и микробиология. 2014. Т. 50. № 4. С. 347–373. https://doi.org/10.7868/S0555109914040187
  33. Самойлова Ю.В., Сорокина К.Н., Пилигаев А.В., Пармон В.Н. // Катализ в промышленности. 2018. Т. 18. № 6. С. 61–73. https://doi.org/10.18412/1816-0387-2018-6-61-73
  34. Röttig A., Steinbüchel A. // Microbiol. Mol. Biol. Rev. 2013. V. 77. № 2. P. 277. https://doi.org/10.1128/MMBR.00010-13
  35. Jarho P., Velde D.V., Stella V.J. // J. Phapm. Sci. 2000. V. 89. №2. P. 241–249. https://doi.org/10.1002/(SICI)1520-6017(200002)89:2<241::AID-JPS11>3.0.CO;2-0
  36. Arun R., Ashok K.C.K., Sravanthi V.V.N.S.S. // Sci Pharm. 2008. V. 76. P. 567–598. https://doi.org/10.3797/scipharm.0808-05
  37. Das S.K., Rajabalaya R., David Sh., Gani N., Khanam J., Nanda A. // RJPBCS. 2013. V. 4. № 2. P. 1694–1720.

Supplementary files

Supplementary Files
Action
1. JATS XML
2.

Download (96KB)
3.

Download (36KB)
4.

Download (122KB)

Copyright (c) 2023 Т.С. Савинова, А.Ю. Аринбасарова, А.В. Казанцев, О.С. Савинова, Н.В. Лукашёв

This website uses cookies

You consent to our cookies if you continue to use our website.

About Cookies