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Synthesis and evaluation as sialidase inhibitors of xylo-configured cyclohexenephosphonates carrying glycerol side-chain mimics
journal contribution
posted on 2023-06-07, 20:59 authored by Hans StreicherBased 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.
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Publication status
- Published
Journal
Bioorganic and Medicinal Chemistry LettersISSN
0960-894XPublisher
ElsevierExternal DOI
Issue
2Volume
14Page range
361-364Pages
4.0Department affiliated with
- Chemistry Publications
Notes
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.Full text available
- No
Peer reviewed?
- Yes
Legacy Posted Date
2012-02-06Usage metrics
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