University of Sussex
Browse

File(s) not publicly available

Synthesis and evaluation as sialidase inhibitors of xylo-configured cyclohexenephosphonates carrying glycerol side-chain mimics

journal contribution
posted on 2023-06-07, 20:59 authored by Hans Streicher
Based on a strategy previously reported by us, we have synthesized D-xylo configured cyclohexenephosphonates designed to mimic the transition state of the sialidase reaction. The double bond orientation corresponds to the benchmark inhibitor Neu5Ac2en and we could selectively introduce hydroxyalkyl substituents in order to simulate the glycerol side-chain of neuraminic acid. The inhibitory activity of a set of compounds towards bacterial sialidases was tested and interesting differences in activity were found. (C) 2003 Elsevier Ltd. All rights reserved.

History

Publication status

  • Published

Journal

Bioorganic and Medicinal Chemistry Letters

ISSN

0960-894X

Publisher

Elsevier

Issue

2

Volume

14

Page range

361-364

Pages

4.0

Department affiliated with

  • Chemistry Publications

Notes

HS directed and executed all the work and is sole author. New methodologies are developed to selectively introduce mimetics of the glycerol side chain of sialic acid into xylo-configured cyclohexenephosphonates. The monoester moiety and a hydroxyethyl side chain give improved sialidase inhibitors, giving valuable insights into future design.

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