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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 BohnerWe 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
TetrahedronISSN
0040-4020Publisher
ElsevierExternal DOI
Issue
38Volume
58Page range
7573-7581Pages
9.0Department 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
2012-02-06Usage metrics
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