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Известия Национальной академии наук Беларуси. Серия химических наук

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Синтез 22- и 23-дегидроксибрассиностероидов стигмастанового ряда

https://doi.org/10.29235/1561-8331-2023-59-3-202-210

Анатацыя

Осуществлен синтез ранее неописанных 22- и 23-дезоксианалогов гомокастастерона, позволяющий получить целевые соединения без замены углеродного скелета боковой цепи. Ключевыми реакциями в их синтезе стали раскрытие эпоксидного цикла и радикальное дебромирование.

Аб аўтарах

В. Хрипач
Институт биоорганической химии Национальной академии наук Беларуси
Беларусь


В. Жабинский
Институт биоорганической химии Национальной академии наук Беларуси
Беларусь


Е. Сикоров
Институт биоорганической химии Национальной академии наук Беларуси
Беларусь


С. Лазарев
Институт биоорганической химии Национальной академии наук Беларуси
Беларусь


Спіс літаратуры

1. Khripach, V. A. Brassinosteroids. A New Class of Plant Hormones / V. A. Khripach, V. N. Zhabinskii, A. E. de Groot. – San Diego: Academic Press, 1999. – 456 c.

2. Bajguz, A. Brassinosteroids – Occurence and Chemical Structures in Plants / A. Bajguz // Brassinosteroids: A Class of Plant Hormone / eds.: S. Hayat, Aqil Ahmad. – Dordrecht, 2011. – P. 1–27. https://doi.org/10.1007/978-94-007-0189-2_1

3. Wei, Z. Regulation of brassinosteroid homeostasis in higher plants / Z. Wei, J. Li // Front. Plant Sci. – 2020. – Vol. 11. – № 583622. https://doi.org/10.3389/fpls.2020.583622

4. The DWF4 gene of Arabidopsis encodes a cytochrome P450 that mediates multiple 22a-hydroxylation steps in bras sinosteroid biosynthesis / S. W. Choe [et al.] // Plant Cell. – 1998. – Vol. 10, № 2. – P. 231–243. https://doi.org/10.1105/tpc.10.2.231

5. Arabidopsis CYP90B1 catalyses the early C-22 hydroxylation of C27, C28 and C29 sterols / S. Fujita [et al.] // Plant J. – 2006. – Vol. 45, № 5. – P. 765–774. https://doi.org/10.1111/j.1365-313X.2005.02639.x

6. CYP724B2 and CYP90B3 function in the early C-22 hydroxylation steps of brassinosteroid biosynthetic pathway in tomato / T. Ohnishi [et al.] // Biosci. Biotechnol. Biochem. – 2006. – Vol. 70, № 9. – P. 2071–2080. https://doi.org/10.1271/bbb.60034

7. Khripach, V. A. Synthetic Aspects of Brassinosteroids / V. A. Khripach, V. N. Zhabinskii, Y. V. Ermolovich // Studies in Natural Products Chemistry / ed. Atta-ur-Rahman. – Amsterdam, 2015. – P. 309–352. https://doi.org/10.1016/B978-0-444-63460-3.00006-7

8. Synthesis of hexadeuterated 23-dehydroxybrassinosteroids / V. A. Khripach [et al.] // Steroids. – 2002. – Vol. 67, № 13–14. – P. 1101–1108. https://doi.org/10.1016/S0039-128X(02)00071-5

9. Synthesis of [26,27-2H6]brassinosteroids from 23,24-bisnorcholenic acid methyl ester / A. P. Antonchick [et al.] // Steroids. – 2004. – Vol. 69, № 10. – P. 617–628. https://doi.org/10.1016/j.steroids.2004.05.014

10. Hurski, A. L. A new approach to the side chain formation of 24-alkyl-22-hydroxy steroids: application to the preparation of early brassinolide biosynthetic precursors / A. L. Hurski, V. N. Zhabinskii, V. A. Khripach // Steroids. – 2012. – Vol. 77, № 7. – P. 780–790. https://doi.org/10.1016/j.steroids.2012.03.010

11. A convenient synthesis of (22S)-22-hydroxycampesterol and some related steroids / S. Takatsuto [et al.] // J. Chem. Res. (S). – 1998. – № 4. – P. 176–177. https://doi.org/10.1039/A707201E

12. A concise and stereoselective synthesis of the cathasterone’s side chain / T. S. Mei [et al.] // Chin. Chem. Lett. – 2004. – Vol. 15. – P. 762–764.

13. Synthesis of cathasterone and its related putative intermediates in brassinolide biosynthesis / S. Takatsuto [et al.] // J. Chem. Res. (S). – 1997. – № 11. – P. 418–419. https://doi.org/10.1039/A704788F

14. Synthesis of 24-epicathasterone and related brassinosteroids with modified side chain / B. Voigt [et al.] // Tetrahedron. – 1997. – Vol. 53, № 50. – P. 17039–17054. https://doi.org/10.1016/S0040-4020(97)10146-6

15. Новый синтез (22S,23S)-28-гомокастастерона / А. А. Ахрем [и др.] // Докл. Акад. наук СССР. – 1984. – Т. 275, № 5. – С. 1089–1091.

16. Fuentes-Figuerо E. Burgueno-Tapia // Chirality. – 2022. – Vol. 34, № 2. – P. 396–420. https://doi.org/10.1002/chir.23390

17. Configurational assignment of epimeric 22,23-epoxides of steroids by C-13 NMR-spectroscopy / M. G. Sierra [et al.] // Tetrahedron. – 1986. – Vol. 42, № 2. – P. 755–758. https://doi.org/10.1016/S0040-4020(01)87482-2

18. Nakane, M. Stereoselectivity in the electrophilic addition reactions of stigmast-22(23)-ene derivatives / M. Nakane, M. Morisaki, N. Ikekawa // Tetrahedron. – 1975. – Vol. 31, № 22. – P. 2755–2760. https://doi.org/10.1016/0040-4020(75)80285-7


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ISSN 1561-8331 (Print)
ISSN 2524-2342 (Online)