Looking glass inhibitors: Efficient synthesis and biological evaluation of D-deoxyfuconojirimycin

Looking glass inhibitors: Efficient synthesis and biological evaluation of D-deoxyfuconojirimycin

Čájet eará veršuvnnaid (1)

1,6-Dideoxygalactostatin, the mirror image of 1-deoxy-L-fuconojirimycin, was efficiently prepared from 2,3-O-isopropylidene-L-lyxonolactone in four steps and evaluated as a glycosidase inhibitor. © 2005 Elsevier Ltd. All rights reserved.

Bibliográfalaš dieđut
Váldodahkkit:	Blériot, Y, Gretzke, D, Krülle, T, Butters, T, Dwek, R, Nash, R, Asano, N, Fleet, G
Materiálatiipa:	Journal article
Giella:	English
Almmustuhtton:	2005

Geahča maid

Looking glass inhibitors: efficient synthesis and biological evaluation of D-deoxyfuconojirimycin.
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Looking glass inhibitors: L-DMDP, a more potent and specific inhibitor of alpha-glucosidases than the enantiomeric natural product DMDP.
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Inhibition of alpha-L-fucosidase by derivatives of deoxyfuconojirimycin and deoxymannojirimycin.
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SHORT EFFICIENT SYNTHESIS OF THE ALPHA-L-FUCOSIDASE INHIBITOR, DEOXYFUCONOJIRIMYCIN [1,5-DIDEOXY-1,5-IMINO-L-FUCITOL] FROM D-LYXONOLACTONE
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Design, synthesis, and biological evaluation of enantiomeric beta-N-acetylhexosaminidase inhibitors LABNAc and DABNAc as potential agents against Tay-Sachs and Sandhoff disease.
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Synthesis of bis(1,3-dihydroxy-isopropyl)amine by reductive amination of dihydroxyacetone: Open chain equivalent of DMDP and a potential AB(4) dendritic monomer
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Mirror image mimics of rhamnose fucose galactose and mannose
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Piperidine analogues of D-galactose as potent inhibitors of alpha-galactosidase: Synthesis by stannane-mediated hydroxymethylation of 5-azido-1,4-lactones. Structural relationships between D-galactosidase and L-rhamnosidase inhibitors
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Almmustuhtton: (1999)

Enantiomeric hexosaminidase inhibitors
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Almmustuhtton: (2005)

Synthesis and biological characterisation of novel N-alkyl-deoxynojirimycin alpha-glucosidase inhibitors.
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Homochiral carbon branched piperidines from carbon branched sugar lactones: 4-C-methyl-deoxyfuconojirimycin (DFJ) and its enantiomer - removal of glycosidase inhibition
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Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application
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Enantiomeric 2-acetamido-1,4-dideoxy-1,4-iminoribitols as potential pyrrolidine hexosaminidase inhibitors
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Molecular requirements of imino sugars for the selective control of N-linked glycosylation and glycosphingolipid biosynthesis
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Improved cellular inhibitors for glycoprotein processing alpha-glucosidases: biological characterisation of alkyl- and arylalkyl-N-substituted deoxynojirimycins
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SYNTHESIS OF 1,5-DIDEOXY-3-O-(ALPHA-D-MANNOPYRANOSYL)-1,5-IMINO-D-MANNITOL AND 1,5-DIDEOXY-3-O-(ALPHA-D-GLUCOPYRANOSYL)-1,5-IMINO-D-MANNITOL - POWERFUL INHIBITORS OF ENDOMANNOSIDASE
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Almmustuhtton: (1993)

Looking glass inhibitors: synthesis of a potent naringinase inhibitor L-DIM [1,4-dideoxy-1,4-imino-L-mannitol], the enantiomer of DIM [1,4-dideoxy-1,4-imino-D-mannitol] a potent alpha-D-mannosidase inhibitor
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DELTA-LACTAMS - SYNTHESIS FROM D-GLUCOSE, AND PRELIMINARY EVALUATION AS A FUCOSIDASE INHIBITOR, OF L-FUCONIC-DELTA-LACTAM
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Sugar amino acids at the anomeric position of carbohydrates: synthesis of spirocyclic amino acids of 6-deoxy-L-lyxofuranose
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Iminosugar inhibitors for treating the lysosomal glycosphingolipidoses
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Imino sugar inhibitors for treating the lysosomal glycosphingolipidoses.
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Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-D-lyxitol [a potent competitive inhibitor of alpha-D-galactosidase] and of 1,4-dideoxy-1,4-imino-L-lyxitol [a weak competitive inhibitor of alpha-D-galactosidase] inhibit naringinase, an alpha-L-rhamnosidase competitively
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Almmustuhtton: (2009)

Mimics of galactofuranose and galactopyranose
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Almmustuhtton: (1997)

Intermediates for incorporation of tetrahydroxypipecolic acid analogues of alpha- and beta-D-mannopyranose into combinatorial libraries: unexpected nanomolar-range hexosaminidase inhibitors. Synthesis of alpha- and beta-homomannojirimycin
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Almmustuhtton: (1998)

Looking-glass synergistic pharmacological chaperones: DGJ and L-DGJ from the enantiomers of tagatose.
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Glycolipids in cell biology and medicine - Introduction
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Stereospecific synthesis of spirohydantoins of beta-glucopyranose: Inhibitors of glycogen phosphorylase
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Synthesis of a novel AB4 monomer and its incorporation into highly branched dendritic structures.
Dahkki: Scott, D, et al.
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Preparation, biochemical characterization and biological properties of radiolabelled N-alkylated deoxynojirimycins.
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Novel mannosidase inhibitors probe glycoprotein degradation pathways in cells.
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Bis(1,3-dihydroxy-isopropyl)amine (BDI) as an AB(4) dendritic building block: rapid synthesis of a second generation dendrimer
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Looking glass inhibitors: scalable syntheses of DNJ, DMDP, and (3R)-3-hydroxy-L-bulgecinine from D-glucuronolactone and of L-DNJ, L-DMDP, and (3S)-3-hydroxy-D-bulgecinine from L-glucuronolactone. DMDP inhibits beta-glucosidases and beta-galactosidases whereas L-DMDP is a potent and specific inhibitor of alpha-glucosidases
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Design and synthesis of acetamido tri- and tetra-hydroxyazepanes: potent and selective beta-N-acetylhexosaminidase inhibitors.
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Strategy for designing selective α-L-rhamnosidase inhibitors: Synthesis and biological evaluation of DMDP cyclic isothioureas
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