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Russian Chemical Bulletin

, Volume 59, Issue 6, pp 1267–1272 | Cite as

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

  • V. V. Veselovsky
  • L. L. Danilov
  • A. N. Vinnikova
  • T. N. Druzhinina
Full Articles

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.

Keywords

undecaprenyl phosphate analog polyprenols van Tamelen epoxidation Mitsunobu reaction phosphorylation O-antigenic polysaccharide assembly cell membranes bacteria Salmonella arizona O:59 bacteria Aeromonas hydrophila AH-1 

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Copyright information

© Springer Science+Business Media, Inc.  2010

Authors and Affiliations

  • V. V. Veselovsky
    • 1
  • L. L. Danilov
    • 1
  • A. N. Vinnikova
    • 1
  • T. N. Druzhinina
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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