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Building a successful structural motif into sialylmimetics - cyclohexenephosphonate monoesters as pseudo-sialosides with promising inhibitory properties
journal contribution
posted on 2023-06-07, 19:45 authored by Hansjorg Streicher, Heike BusseA variable synthesis of a new class of sialylmimetics which provides access to pseudo-sialosides containing the successful cyclohexene motif in the sialic acid mimicking part has been developed. The D- and L-xylo cyclohexenephosphonate scaffolds allow attachment of selected aglycones or aglycon mimics via mixed phosphonate diester strategies and some target compounds thus synthesized displayed promising inhibitory properties when tested with parasitic or bacterial sialidases.
History
Publication status
- Published
Journal
Bioorganic and Medicinal ChemistryISSN
0968-0896Publisher
Series Title: Methods in EnzymologyExternal DOI
Issue
4Volume
14Page range
1047-1057Pages
11.0Department affiliated with
- Chemistry Publications
Notes
HS directed the work, is corresponding author and grantholder. First demonstration of a synthetic strategy which allows the attachment of xylo-configured cyclohexenephosphonates as carbocyclic sialylmimetics to sugars via the phosphonate monoester moiety which allows incorporation of the cyclohexene motif (Tamiflu-motif), into disaccharide mimetics.Full text available
- No
Peer reviewed?
- Yes
Legacy Posted Date
2012-02-06Usage metrics
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