Building a successful structural motif into sialylmimetics - cyclohexenephosphonate monoesters as pseudo-sialosides with promising inhibitory properties

Streicher, Hansjorg and Busse, Heike (2006) Building a successful structural motif into sialylmimetics - cyclohexenephosphonate monoesters as pseudo-sialosides with promising inhibitory properties. Bioorganic & Medicinal Chemistry, 14 (4). pp. 1047-1057. ISSN 0968-0896

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Abstract

A 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.

Item Type: Article
Additional Information: 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.
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Hans Streicher
Date Deposited: 06 Feb 2012 18:22
Last Modified: 16 Mar 2012 15:34
URI: http://sro.sussex.ac.uk/id/eprint/16006
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