Probing the aglycon binding site of a beta-glucosidase: a collection of C-1-modified 2,5-dideoxy-2,5-imino-D-mannitol derivatives and their structure-activity relationships as competitive inhibitors

Tanja M Wrodnigg; Frederik Diness; Christoph Gruber; Herwig Häusler; Inge Lundt; Karen Rupitz; Andreas J Steiner; Arnold E Stütz; Chris A Tarling; Stephen G Withers; Heidrun Wölfler

doi:10.1016/j.bmc.2004.04.037

Probing the aglycon binding site of a beta-glucosidase: a collection of C-1-modified 2,5-dideoxy-2,5-imino-D-mannitol derivatives and their structure-activity relationships as competitive inhibitors

Tanja M Wrodnigg, Frederik Diness, Christoph Gruber, Herwig Häusler, Inge Lundt, Karen Rupitz, Andreas J Steiner, Arnold E Stütz, Chris A Tarling, Stephen G Withers, Heidrun Wölfler

Department of Chemistry

40 Citations (Scopus)

Abstract

A range of new C-1 modified derivatives of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol has been synthesised and their biological activities probed with the beta-glucosidase from Agrobacterium sp. Ki values are compared with those of previously prepared close relatives. Findings suggest dramatic effects exerted by the aglycon binding site on substrate/inhibitor binding.

Original language	English
Journal	Bioorganic & Medicinal Chemistry
Volume	12
Issue number	13
Pages (from-to)	3485-95
Number of pages	11
ISSN	0968-0896
DOIs	https://doi.org/10.1016/j.bmc.2004.04.037
Publication status	Published - 1 Jul 2004

Keywords

Binding, Competitive
Enzyme Inhibitors
Imino Pyranoses
Mannitol
Molecular Structure
Rhizobium
Structure-Activity Relationship
beta-Glucosidase

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Wrodnigg, T. M., Diness, F., Gruber, C., Häusler, H., Lundt, I., Rupitz, K., Steiner, A. J., Stütz, A. E., Tarling, C. A., Withers, S. G., & Wölfler, H. (2004). Probing the aglycon binding site of a beta-glucosidase: a collection of C-1-modified 2,5-dideoxy-2,5-imino-D-mannitol derivatives and their structure-activity relationships as competitive inhibitors. Bioorganic & Medicinal Chemistry, 12(13), 3485-95. https://doi.org/10.1016/j.bmc.2004.04.037

Probing the aglycon binding site of a beta-glucosidase : a collection of C-1-modified 2,5-dideoxy-2,5-imino-D-mannitol derivatives and their structure-activity relationships as competitive inhibitors. / Wrodnigg, Tanja M; Diness, Frederik; Gruber, Christoph et al.

In: Bioorganic & Medicinal Chemistry, Vol. 12, No. 13, 01.07.2004, p. 3485-95.

Research output: Contribution to journal › Journal article › Research › peer-review

Wrodnigg, TM, Diness, F, Gruber, C, Häusler, H, Lundt, I, Rupitz, K, Steiner, AJ, Stütz, AE, Tarling, CA, Withers, SG & Wölfler, H 2004, 'Probing the aglycon binding site of a beta-glucosidase: a collection of C-1-modified 2,5-dideoxy-2,5-imino-D-mannitol derivatives and their structure-activity relationships as competitive inhibitors', Bioorganic & Medicinal Chemistry, vol. 12, no. 13, pp. 3485-95. https://doi.org/10.1016/j.bmc.2004.04.037

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abstract = "A range of new C-1 modified derivatives of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol has been synthesised and their biological activities probed with the beta-glucosidase from Agrobacterium sp. Ki values are compared with those of previously prepared close relatives. Findings suggest dramatic effects exerted by the aglycon binding site on substrate/inhibitor binding.",

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AU - Wrodnigg, Tanja M

AU - Diness, Frederik

AU - Gruber, Christoph

AU - Häusler, Herwig

AU - Lundt, Inge

AU - Rupitz, Karen

AU - Steiner, Andreas J

AU - Stütz, Arnold E

AU - Tarling, Chris A

AU - Withers, Stephen G

AU - Wölfler, Heidrun

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AB - A range of new C-1 modified derivatives of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol has been synthesised and their biological activities probed with the beta-glucosidase from Agrobacterium sp. Ki values are compared with those of previously prepared close relatives. Findings suggest dramatic effects exerted by the aglycon binding site on substrate/inhibitor binding.

KW - Binding, Competitive

KW - Enzyme Inhibitors

KW - Imino Pyranoses

KW - Mannitol

KW - Molecular Structure

KW - Rhizobium

KW - Structure-Activity Relationship

KW - beta-Glucosidase

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DO - 10.1016/j.bmc.2004.04.037

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SN - 0968-0896

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JO - Bioorganic & Medicinal Chemistry

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Probing the aglycon binding site of a beta-glucosidase: a collection of C-1-modified 2,5-dideoxy-2,5-imino-D-mannitol derivatives and their structure-activity relationships as competitive inhibitors

Abstract

Keywords

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