A concise synthetic approach for isoiminosugars

Martin Simon Thonhofer; Andre Stephan Culum; Tobias Dorn; Roland C. Fischer; Herwig Anton Prasch; Arnold Stütz; Patrick Weber; Tanja Maria  Wrodnigg

doi:10.1016/j.carres.2024.109239

A concise synthetic approach for isoiminosugars

Martin Simon Thonhofer^*, Andre Stephan Culum, Tobias Dorn, Roland C. Fischer, Herwig Anton Prasch, Arnold Stütz, Patrick Weber, Tanja Maria Wrodnigg

^*Corresponding author for this work

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

Abstract

Isoiminosugars are highly biological active substances. Herein, we report a concise synthetic approach for this class of compounds. The key step relies on a stereospecific 1,2-hydride shift in O-2 tosylated glycopyranosides leading to C-2 branched glycofuranosides. This approach enables a 4-step synthesis of powerful β-galactosidase inhibitor 4-epi-isofagomine starting from a simple D-glucopyranoside.

Original language	English
Article number	109239
Pages (from-to)	1-5
Number of pages	5
Journal	Carbohydrate Research
Volume	544
Issue number	544
Early online date	10 Aug 2024
DOIs	https://doi.org/10.1016/j.carres.2024.109239
Publication status	Published - Oct 2024

Keywords

4-epi-isofagomine
Glycosid hydrolases
Inhibitor
Isoiminosugar
Synthesis

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/j.carres.2024.109239

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title = "A concise synthetic approach for isoiminosugars",

abstract = "Isoiminosugars are highly biological active substances. Herein, we report a concise synthetic approach for this class of compounds. The key step relies on a stereospecific 1,2-hydride shift in O-2 tosylated glycopyranosides leading to C-2 branched glycofuranosides. This approach enables a 4-step synthesis of powerful β-galactosidase inhibitor 4-epi-isofagomine starting from a simple D-glucopyranoside.",

keywords = "4-epi-isofagomine, Glycosid hydrolases, Inhibitor, Isoiminosugar, Synthesis",

author = "Thonhofer, {Martin Simon} and Culum, {Andre Stephan} and Tobias Dorn and Fischer, {Roland C.} and Prasch, {Herwig Anton} and Arnold St{\"u}tz and Patrick Weber and Wrodnigg, {Tanja Maria}",

year = "2024",

month = oct,

doi = "10.1016/j.carres.2024.109239",

language = "English",

volume = "544",

pages = "1--5",

journal = "Carbohydrate Research",

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T1 - A concise synthetic approach for isoiminosugars

AU - Thonhofer, Martin Simon

AU - Culum, Andre Stephan

AU - Dorn, Tobias

AU - Fischer, Roland C.

AU - Prasch, Herwig Anton

AU - Stütz, Arnold

AU - Weber, Patrick

AU - Wrodnigg, Tanja Maria

PY - 2024/10

Y1 - 2024/10

N2 - Isoiminosugars are highly biological active substances. Herein, we report a concise synthetic approach for this class of compounds. The key step relies on a stereospecific 1,2-hydride shift in O-2 tosylated glycopyranosides leading to C-2 branched glycofuranosides. This approach enables a 4-step synthesis of powerful β-galactosidase inhibitor 4-epi-isofagomine starting from a simple D-glucopyranoside.

AB - Isoiminosugars are highly biological active substances. Herein, we report a concise synthetic approach for this class of compounds. The key step relies on a stereospecific 1,2-hydride shift in O-2 tosylated glycopyranosides leading to C-2 branched glycofuranosides. This approach enables a 4-step synthesis of powerful β-galactosidase inhibitor 4-epi-isofagomine starting from a simple D-glucopyranoside.

KW - 4-epi-isofagomine

KW - Glycosid hydrolases

KW - Inhibitor

KW - Isoiminosugar

KW - Synthesis

UR - https://www.sciencedirect.com/science/article/pii/S0008621524002180?dgcid=coauthor

UR - http://www.scopus.com/inward/record.url?scp=85200979616&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2024.109239

DO - 10.1016/j.carres.2024.109239

M3 - Article

SN - 0008-6215

VL - 544

SP - 1

EP - 5

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 544

M1 - 109239

ER -

A concise synthetic approach for isoiminosugars

Abstract

Keywords

ASJC Scopus subject areas

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