Synthesis of functionalized cyclohexenephosphonates and their inhibitory activity towards bacterial sialidases

Streicher, Hansjorg and Bohner, Christoph (2002) Synthesis of functionalized cyclohexenephosphonates and their inhibitory activity towards bacterial sialidases. Tetrahedron, 58 (38). pp. 7573-7581. ISSN 0040-4020

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Abstract

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.

Item Type: Article
Additional Information: 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.
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Hans Streicher
Date Deposited: 06 Feb 2012 20:57
Last Modified: 28 Mar 2012 15:18
URI: http://sro.sussex.ac.uk/id/eprint/28843
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