University of Sussex
Browse

File(s) not publicly available

Synthesis of functionalized cyclohexenephosphonates and their inhibitory activity towards bacterial sialidases

journal contribution
posted on 2023-06-08, 08:20 authored by Hansjorg Streicher, Christoph Bohner
We have synthesized a series of cyclohexenephosphonates derived from D- and L-xylose, designed as core structures for the development of high affinity mimics of sialic acid and of the sialidase reaction transition state, Extension of our syntheses to both xylose enantiomers has given us access to two series of cyclohexenephosphonates with regioisomeric double bonds. We have demonstrated the selective functionalization of the hydroxyl groups towards introduction of a glycerol side chain mimic and immobilization via a silyl linker. The inhibitory activity of a selected set of compounds towards three bacterial sialidases has been tested and moderate activity was found. (C) 2002 Elsevier Science Ltd. All rights reserved.

History

Publication status

  • Published

Journal

Tetrahedron

ISSN

0040-4020

Publisher

Elsevier

Issue

38

Volume

58

Page range

7573-7581

Pages

9.0

Department affiliated with

  • Chemistry Publications

Notes

HS directed the work and is corresponding author and grantholder. First use of an effective and variable chiral-pool synthesis for D- and L-xylo configured cyclohexenephosphonates from D- and L-xylose, respectively. Effective sialic acid mimicry was demonstrated by the inhibition of various bacterial sialidases.

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2012-02-06

Usage metrics

    University of Sussex (Publications)

    Categories

    No categories selected

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC