Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols.

Peter Greimel; Herwig Häusler; Inge Lundt; Karen Rupitz; Arnold E. Stütz; Chris A. Tarling; Stephen G. Withers; Tanja M. Wrodnigg

Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols.

Peter Greimel, Herwig Häusler, Inge Lundt, Karen Rupitz, Arnold E. Stütz, Chris A. Tarling, Stephen G. Withers, Tanja M. Wrodnigg

Department of Chemistry

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

Abstract

1,5-Dideoxy-1,5-iminoalditols of various configurations as well as isofagomine were N-alkylated with non-polar straight chain spacer-arms by a set of simple standard procedures. The spacer-arms’ terminal functional groups, primary amines, were employed to introduce fluorescent tags such as dansyl and dapoxyl moieties. Resulting derivatives in the D-xylo, D-gluco, D-galacto as well as GlcNAc series showed distinctly improved glycosidase inhibitory activities compared to parent compounds and are designed to be useful analytical tools.

Original language	English
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	16
Pages (from-to)	2067-2070
ISSN	0960-894X
Publication status	Published - 2006

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title = "Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols.",

abstract = "1,5-Dideoxy-1,5-iminoalditols of various configurations as well as isofagomine were N-alkylated with non-polar straight chain spacer-arms by a set of simple standard procedures. The spacer-arms{\textquoteright} terminal functional groups, primary amines, were employed to introduce fluorescent tags such as dansyl and dapoxyl moieties. Resulting derivatives in the D-xylo, D-gluco, D-galacto as well as GlcNAc series showed distinctly improved glycosidase inhibitory activities compared to parent compounds and are designed to be useful analytical tools.",

author = "Peter Greimel and Herwig H{\"a}usler and Inge Lundt and Karen Rupitz and St{\"u}tz, {Arnold E.} and Tarling, {Chris A.} and Withers, {Stephen G.} and Wrodnigg, {Tanja M.}",

year = "2006",

language = "English",

volume = "16",

pages = "2067--2070",

journal = "Bioorganic & Medicinal Chemistry Letters",

issn = "0960-894X",

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TY - JOUR

T1 - Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols.

AU - Greimel, Peter

AU - Häusler, Herwig

AU - Lundt, Inge

AU - Rupitz, Karen

AU - Stütz, Arnold E.

AU - Tarling, Chris A.

AU - Withers, Stephen G.

AU - Wrodnigg, Tanja M.

PY - 2006

Y1 - 2006

N2 - 1,5-Dideoxy-1,5-iminoalditols of various configurations as well as isofagomine were N-alkylated with non-polar straight chain spacer-arms by a set of simple standard procedures. The spacer-arms’ terminal functional groups, primary amines, were employed to introduce fluorescent tags such as dansyl and dapoxyl moieties. Resulting derivatives in the D-xylo, D-gluco, D-galacto as well as GlcNAc series showed distinctly improved glycosidase inhibitory activities compared to parent compounds and are designed to be useful analytical tools.

AB - 1,5-Dideoxy-1,5-iminoalditols of various configurations as well as isofagomine were N-alkylated with non-polar straight chain spacer-arms by a set of simple standard procedures. The spacer-arms’ terminal functional groups, primary amines, were employed to introduce fluorescent tags such as dansyl and dapoxyl moieties. Resulting derivatives in the D-xylo, D-gluco, D-galacto as well as GlcNAc series showed distinctly improved glycosidase inhibitory activities compared to parent compounds and are designed to be useful analytical tools.

M3 - Journal article

SN - 0960-894X

VL - 16

SP - 2067

EP - 2070

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

ER -