Synthesis and biological evaluation of novel biotin-iminoalditol conjugates

Gerit Pototschnig; Christian Morales De Csáky; Jose R Montenegro Burke; Georg Schitter; Arnold E Stütz; Chris A Tarling; Stephen G Withers; Tanja M Wrodnigg

doi:10.1016/j.bmcl.2010.05.084

Synthesis and biological evaluation of novel biotin-iminoalditol conjugates

Gerit Pototschnig, Christian Morales De Csáky, Jose R Montenegro Burke, Georg Schitter, Arnold E Stütz, Chris A Tarling, Stephen G Withers, Tanja M Wrodnigg

Institute of Organic Chemistry (6410)

Research output: Contribution to journal › Article › peer-review

Abstract

Biotin-iminosugar conjugates of different configuration such as D-gluco, D-galacto, L-ido as well as a furanoid representative in the D-manno configuration have been synthesised and exhibit powerful inhibition of beta-glucosidase from Agrobacterium sp. with K(i) values in the range of the respective parent compounds. Such molecular probes have potential for activity-based protein profiling taking advantage of the biotin-(strept)avidin interaction.

Original language	English
Pages (from-to)	4077-9
Number of pages	3
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	20
Issue number	14
DOIs	https://doi.org/10.1016/j.bmcl.2010.05.084
Publication status	Published - 15 Jul 2010

Keywords

Biotin/chemical synthesis
Drug Evaluation, Preclinical
Molecular Probes
Sugar Alcohols/chemical synthesis

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10.1016/j.bmcl.2010.05.084

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title = "Synthesis and biological evaluation of novel biotin-iminoalditol conjugates",

abstract = "Biotin-iminosugar conjugates of different configuration such as D-gluco, D-galacto, L-ido as well as a furanoid representative in the D-manno configuration have been synthesised and exhibit powerful inhibition of beta-glucosidase from Agrobacterium sp. with K(i) values in the range of the respective parent compounds. Such molecular probes have potential for activity-based protein profiling taking advantage of the biotin-(strept)avidin interaction.",

keywords = "Biotin/chemical synthesis, Drug Evaluation, Preclinical, Molecular Probes, Sugar Alcohols/chemical synthesis",

author = "Gerit Pototschnig and {De Cs{\'a}ky}, {Christian Morales} and Burke, {Jose R Montenegro} and Georg Schitter and St{\"u}tz, {Arnold E} and Tarling, {Chris A} and Withers, {Stephen G} and Wrodnigg, {Tanja M}",

year = "2010",

month = jul,

day = "15",

doi = "10.1016/j.bmcl.2010.05.084",

language = "English",

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pages = "4077--9",

journal = "Bioorganic & Medicinal Chemistry Letters",

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TY - JOUR

T1 - Synthesis and biological evaluation of novel biotin-iminoalditol conjugates

AU - Pototschnig, Gerit

AU - De Csáky, Christian Morales

AU - Burke, Jose R Montenegro

AU - Schitter, Georg

AU - Stütz, Arnold E

AU - Tarling, Chris A

AU - Withers, Stephen G

AU - Wrodnigg, Tanja M

PY - 2010/7/15

Y1 - 2010/7/15

N2 - Biotin-iminosugar conjugates of different configuration such as D-gluco, D-galacto, L-ido as well as a furanoid representative in the D-manno configuration have been synthesised and exhibit powerful inhibition of beta-glucosidase from Agrobacterium sp. with K(i) values in the range of the respective parent compounds. Such molecular probes have potential for activity-based protein profiling taking advantage of the biotin-(strept)avidin interaction.

AB - Biotin-iminosugar conjugates of different configuration such as D-gluco, D-galacto, L-ido as well as a furanoid representative in the D-manno configuration have been synthesised and exhibit powerful inhibition of beta-glucosidase from Agrobacterium sp. with K(i) values in the range of the respective parent compounds. Such molecular probes have potential for activity-based protein profiling taking advantage of the biotin-(strept)avidin interaction.

KW - Biotin/chemical synthesis

KW - Drug Evaluation, Preclinical

KW - Molecular Probes

KW - Sugar Alcohols/chemical synthesis

U2 - 10.1016/j.bmcl.2010.05.084

DO - 10.1016/j.bmcl.2010.05.084

M3 - Article

C2 - 20610152

SN - 0960-894X

VL - 20

SP - 4077

EP - 4079

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 14

ER -

Synthesis and biological evaluation of novel biotin-iminoalditol conjugates

Abstract

Keywords

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