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An undecaprenyl phosphate analog containing the phenoxy group at the ω-end of the oligoisoprene chain

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Abstract

A simple method for the preparation of a biologically active analog of bacterial undecaprenyl phosphate bearing the phenoxy group at the ω-end of the chain was developed on the basis of accessible polyprenols from mulberry (Morus nigra) leaves. It includes the selective van Tamelen epoxidation of the ω-terminal isoprene unit of polyprenyl acetates, conversion of the epoxides into ω-terminal aldehydes, their hydride reduction into hydroxy acetates followed by the Mitsunobu condensation with phenol, and phosphorylation of the resulting phenoxy alcohols. The biological activity of the obtained phosphates was tested by the radiometry method in the initiation of O-antigenic polysaccharide assembly reaction using the cell membrane preparations from the Gram-negative bacteria Salmonella arizona O:59 and Aeromonas hydrophila AH-1.

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References

  1. V. N. Shibaev, Adv. Carbohydr. Chem. Biochem., 1986, 44, 277.

    Article  CAS  Google Scholar 

  2. L. L. Danilov, T. N. Druzhinina, N. A. Kalinchuk, S. D. Maltsev, V. N. Shibaev, Chem. Phys. Lipids, 1989, 51, 191.

    Article  CAS  Google Scholar 

  3. X.-Y. Ye, M.-C. Lo, L. Brunner, D. Walker, D. Kahne, S. Walker, J. Am. Chem, Soc., 2001, 123, 3155.

    Article  CAS  Google Scholar 

  4. Y. Zhang, E. Y. Fechter, T.-S. Wang, D. Barrett, S. Walker, D. E. Kahne, J. Am. Chem. Soc., 2007, 129, 3080.

    Article  CAS  Google Scholar 

  5. B. Al-Dabbagh, D. Mengin-Lecreux, A. Bouhss, J. Bacteriol., 2008, 190, 7141.

    Article  CAS  Google Scholar 

  6. B. Al-Dabbagh, D. Blanot, D. Mengin-Lecreux, A. Bouhss, Anal. Biochem., 2009, 391, 163.

    Article  CAS  Google Scholar 

  7. A. Liav, E. Ciepichal, E. Swiezevska, A. Bobovska, P. Dianis- kova, J. Blasko, K. Mikusova, P. J. Brennan, Tetrahedron Lett., 2009, 50, 2242.

    Article  CAS  Google Scholar 

  8. J. P. Montoya-Peleaz, J. G. Riley, W. A. Szarek, M. A. Valvani, J. S. Schutzbach, I. Brockhausen, Bioorgan. Med. Chem. Lett., 2005, 15, 1205.

    Article  CAS  Google Scholar 

  9. J. G. Riley, M. Menggad, J. P. Montoya-Peleaz, W. A. Szarek, C. L. Marolda, M. A. Valvano, J. S. Schutzbach, I. Brockhausen, Glycobiology, 2005, 15, 605–613.

    Article  CAS  Google Scholar 

  10. W. Yi, Q. Yao, Y. Zhang, E. Motari, S. Lin, P. G. Wang, Biochem. Biophys. Res. Com., 2006, 344, 631–639.

    Article  CAS  Google Scholar 

  11. L. L. Danilov, V. V. Veselovsky, N. M. Balagurova, T. N. Druzhinina, Bioorgan. Khim., 2009, 35, 431 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2009, 35].

    CAS  Google Scholar 

  12. E. Swiezewska, W. Sasak, T. Mankowski, W. Jankowski, T. Vogtman, I. Krajewska, J. Hertel, E. Skoczylas, T. Chojnacki, Acta Biochim. Polonica, 1994, 41, 222.

    Google Scholar 

  13. Eur. J. Biochem., 1987, 167, 181–184.

    Google Scholar 

  14. E. E. van Tamelen, T. J. Curphey, Tetrahedron Lett., 1962, 121

  15. E. E. van Tamelen, K. B. Sharpless, Tetrahedron Lett., 1967, 2655

  16. S. Handa, G. Pattenden, J. Chem. Soc., Perkin Trans. 1, 1999, 843.

  17. V. N. Shibaev, V. V. Veselovsky, A. V. Lozanova, S. D. Maltsev, L. L. Danilov, W. T. Forsee, J. Xing, H. C. Cheung, M. J. Jedrzejas, Bioorg. Med. Chem. Lett., 2000, 10, 189

    Article  CAS  Google Scholar 

  18. V. V. Veselovsky, A. V. Lozanova, S. D. Maltsev, L. L. Danilov, V. N. Shibaev, M. J. Jedrzejas, Izv. Akad. Nauk, Ser. Khim., 2001, 2121 [Russ. Chem. Bull., Int. Ed., 2001, 50, 2221].

    Google Scholar 

  19. L. L. Danilov, V. N. Shibaev, in Studies in Natural Products Chemistry, Ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1991, 8, 63.

    Google Scholar 

  20. F. Bohlmann, R. Zeisberg, E. Klein, Org. Magn. Res., 1975, 7, 426.

    Article  CAS  Google Scholar 

  21. L. L. Danilov, S. D. Maltsev, V. N. Shibaev, N. K. Kochetkov, Carbohydrate Res., 1981, 88, 203.

    Article  CAS  Google Scholar 

  22. V. N. Shibaev, Yu. Yu. Kusov, T. N. Druzhinina, N. A. Kalinchuk, N. K. Kochetkov, V. A. Kilesso, S. Sh. Rozhnova, Bioorgan. Khim., 1978, 4, 47 [Sov. J. Bioorg. Chem. (Engl. Transl.), 1978, 4].

    CAS  Google Scholar 

  23. K. Ibata, M. Mizuno, Y. Tanaka, A. Kageyu, Phytochemistry, 1984, 23, 763.

    Google Scholar 

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. V. Veselovsky, L. L. Danilov, A. N. Vinnikova & T. N. Druzhinina

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  1. V. V. Veselovsky
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  2. L. L. Danilov
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  3. A. N. Vinnikova
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  4. T. N. Druzhinina
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Correspondence to V. V. Veselovsky.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1240–1244, June, 2010.

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Veselovsky, V.V., Danilov, L.L., Vinnikova, A.N. et al. An undecaprenyl phosphate analog containing the phenoxy group at the ω-end of the oligoisoprene chain. Russ Chem Bull 59, 1267–1272 (2010). https://doi.org/10.1007/s11172-010-0231-z

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  • DOI: https://doi.org/10.1007/s11172-010-0231-z

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