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Synthesis and biological analysis of novel glycoside derivatives of L-AEP, as targeted antibacterial agents

Bovill, R., Evans, P. G., Howse, G. L. and Osborn, H. M. I. (2016) Synthesis and biological analysis of novel glycoside derivatives of L-AEP, as targeted antibacterial agents. Bioorganic & Medicinal Chemistry Letters, 26 (15). pp. 3774-3779. ISSN 0960-894X

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To link to this item DOI: 10.1016/j.bmcl.2016.05.052

Abstract/Summary

To develop targeted methods for treating bacterial infections, the feasibility of using glycoside derivatives of the antibacterial compound L-R-aminoethylphosphonic acid (L-AEP) has been investigated. These derivatives are hypothesized to be taken up by bacterial cells via carbohydrate uptake mechanisms, and then hydrolysed in situ by bacterial borne glycosidase enzymes, to selectively afford L-AEP. Therefore the synthesis and analysis of ten glycoside derivatives of L-AEP, for selective targeting of specific bacteria, is reported. The ability of these derivatives to inhibit the growth of a panel of Gram-negative bacteria in two different media is discussed. β-Glycosides (12a) and (12b) that contained L-AEP linked to glucose or galactose via a carbamate linkage inhibited growth of a range of organisms with the best MICs being <0.75 mg/ml; for most species the inhibition was closely related to the hydrolysis of the equivalent chromogenic glycosides. This suggests that for (12a) and (12b), release of L-AEP was indeed dependent upon the presence of the respective glycosidase enzyme.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Medicinal Chemistry Research Group
ID Code:65664
Publisher:Elsevier

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