Probing the aglycon binding site of a b-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 Wrodnigg; Frederik Diness; Christoph Gruber; Herwig Häusler; Inge Lundt; Karen Rupitz; Andreas 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 b-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 Wrodnigg
, Frederik Diness
, Christoph Gruber
, Herwig Häusler
, Inge Lundt
, Karen Rupitz
, Andreas Steiner
, Arnold E. Stütz
, Chris A. Tarling
, Stephen G. Withers
, Heidrun Wölfler

Department of Chemistry

Technische Universität Graz

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

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 b-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)	3485-3495
ISSN	0968-0896
DOIs	https://doi.org/10.1016/j.bmc.2004.04.037
Publication status	Published - 2004

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Wrodnigg, T., Diness, F., Gruber, C., Häusler, H., Lundt, I., Rupitz, K., Steiner, A., Stütz, A. E., Tarling, C. A., Withers, S. G., & Wölfler, H. (2004). Probing the aglycon binding site of a b-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), 3485-3495. https://doi.org/10.1016/j.bmc.2004.04.037

@article{77f7d78f56594f03ae1512ed5854f593,

title = "Probing the aglycon binding site of a b-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 = "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 b-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.",

author = "Tanja Wrodnigg and Frederik Diness and Christoph Gruber and Herwig H{\"a}usler and Inge Lundt and Karen Rupitz and Andreas Steiner and St{\"u}tz, \{Arnold E.\} and Tarling, \{Chris A.\} and Withers, \{Stephen G.\} and Heidrun W{\"o}lfler",

year = "2004",

doi = "10.1016/j.bmc.2004.04.037",

language = "English",

volume = "12",

pages = "3485--3495",

journal = "Bioorganic \& Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier",

number = "13",

}

Wrodnigg, T, Diness, F, Gruber, C, Häusler, H, Lundt, I, Rupitz, K, Steiner, A, Stütz, AE, Tarling, CA, Withers, SG & Wölfler, H 2004, 'Probing the aglycon binding site of a b-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. 3485-3495. https://doi.org/10.1016/j.bmc.2004.04.037

Probing the aglycon binding site of a b-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; Diness, Frederik; Gruber, Christoph et al.
In: Bioorganic & Medicinal Chemistry, Vol. 12, No. 13, 2004, p. 3485-3495.

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

TY - JOUR

T1 - Probing the aglycon binding site of a b-glucosidase: a collection of C-1-modified 2,5-dideoxy-2,5-imino-D-mannitol derivatives and their structure-activity relationships as competitive inhibitors

AU - Wrodnigg, Tanja

AU - Diness, Frederik

AU - Gruber, Christoph

AU - Häusler, Herwig

AU - Lundt, Inge

AU - Rupitz, Karen

AU - Steiner, Andreas

AU - Stütz, Arnold E.

AU - Tarling, Chris A.

AU - Withers, Stephen G.

AU - Wölfler, Heidrun

PY - 2004

Y1 - 2004

N2 - 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 b-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.

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 b-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.

U2 - 10.1016/j.bmc.2004.04.037

DO - 10.1016/j.bmc.2004.04.037

M3 - Journal article

SN - 0968-0896

VL - 12

SP - 3485

EP - 3495

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

IS - 13

ER -

Probing the aglycon binding site of a b-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

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