Synthesis and evaluation of N-alkylated analogues of aza-galacto-fagomine – potential pharmacological chaperones for Krabbe disease

Viuff, Agnete H.; Jensen, Henrik H.

doi:10.1039/c6ob01309k

Cited by 4 publications

(1 citation statement)

References 27 publications

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“…This conformational change stabilizes the protein and allows it to evade the quality control mechanisms that lead to protein degradation and reach its final biological destination. We have studied and characterized a series of ligands and their binding to native GALC and thereby their potential as pharmacological chaperones against Krabbe disease. , …”

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The Bicyclic Form of galacto-Noeurostegine Is a Potent Inhibitor of β-Galactocerebrosidase

Viuff

Salamone

McLoughlin

et al. 2020

ACS Med. Chem. Lett.

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Competitive inhibitors of galactocerebrosidase (GALC) could be candidates for pharmacological chaperone therapy of patients with Krabbe disease. The known and selective nortropane-type iminosugar galacto-noeurostegine has been found to competitively inhibit GALC with K i = 7 μM at pH 4.6, which is 330-fold more potent than the analogous deoxynoeurostegine. It was shown through X-ray protein crystallography that galacto-noeurostegine binds to the active site of GALC in its bicyclic form.

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confidence: 99%

The Bicyclic Form of galacto-Noeurostegine Is a Potent Inhibitor of β-Galactocerebrosidase

Viuff

Salamone

McLoughlin

et al. 2020

ACS Med. Chem. Lett.

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Combining Organocatalyzed Aldolization and Reductive Amination: An Efficient Reaction Sequence for the Synthesis of Iminosugars

Ferjancic

Saičić

2021

Eur J Org Chem

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Over the past two decades, organocatalytic aldol reaction emerged as a powerful method for the enantioselective carbon-carbon bond formation, often offering more efficient, economical and environmentally friendly synthesis of chiral molecules. On the other hand, reductive amination is one of the most important reactions in synthesis of biologically active compounds and drug candidates. Coupling these two reactions results in a powerful combination that allows for a rapid, stereoselective access to substituted, highly functionalized fiveand six-membered N-heterocycles. This minireview illustrates the applicability of this approach as the key feature in syntheses of various iminosugars -a class of polyhydroxylated alkaloids with a range of interesting biological activities and high pharmacological potential.

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X-Ray Crystallography in Structure-Function Characterization of Therapeutic Enzymes

Papageorgiou

2019

Advances in Experimental Medicine and Biology

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Synthesis and evaluation of N-alkylated analogues of aza-galacto-fagomine – potential pharmacological chaperones for Krabbe disease

Cited by 4 publications

References 27 publications

The Bicyclic Form of galacto-Noeurostegine Is a Potent Inhibitor of β-Galactocerebrosidase

The Bicyclic Form of galacto-Noeurostegine Is a Potent Inhibitor of β-Galactocerebrosidase

Combining Organocatalyzed Aldolization and Reductive Amination: An Efficient Reaction Sequence for the Synthesis of Iminosugars

X-Ray Crystallography in Structure-Function Characterization of Therapeutic Enzymes

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