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

Streicher, Hans (2004) Synthesis and evaluation as sialidase inhibitors of xylo-configured cyclohexenephosphonates carrying glycerol side-chain mimics. Bioorganic & Medicinal Chemistry Letters, 14 (2). pp. 361-364. ISSN 0960894X

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Abstract

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.

Item Type: Article
Additional Information: 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.
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Hans Streicher
Date Deposited: 06 Feb 2012 18:41
Last Modified: 31 May 2012 14:27
URI: http://sro.sussex.ac.uk/id/eprint/17776
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