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

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.

Manylion Llyfryddiaeth
Prif Awduron:	Blériot, Y, Gretzke, D, Krülle, T, Butters, T, Dwek, R, Nash, R, Asano, N, Fleet, G
Fformat:	Journal article
Iaith:	English
Cyhoeddwyd:	2005

Eitemau Tebyg

Looking glass inhibitors: efficient synthesis and biological evaluation of D-deoxyfuconojirimycin.
gan: Blériot, Y, et al.
Cyhoeddwyd: (2005)

Looking glass inhibitors: L-DMDP, a more potent and specific inhibitor of α-glucosidases than the enantiomeric natural product DMDP
gan: Yu, C, et al.
Cyhoeddwyd: (2004)

Looking glass inhibitors: L-DMDP, a more potent and specific inhibitor of alpha-glucosidases than the enantiomeric natural product DMDP.
gan: Yu, C, et al.
Cyhoeddwyd: (2004)

Inhibition of alpha-L-fucosidase by derivatives of deoxyfuconojirimycin and deoxymannojirimycin.
gan: Winchester, B, et al.
Cyhoeddwyd: (1990)

SHORT EFFICIENT SYNTHESIS OF THE ALPHA-L-FUCOSIDASE INHIBITOR, DEOXYFUCONOJIRIMYCIN [1,5-DIDEOXY-1,5-IMINO-L-FUCITOL] FROM D-LYXONOLACTONE
gan: Fleet, G, et al.
Cyhoeddwyd: (1989)

Efficient synthesis from D-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-L-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases
gan: Rountree, J, et al.
Cyhoeddwyd: (2007)

Design, synthesis, and biological evaluation of enantiomeric beta-N-acetylhexosaminidase inhibitors LABNAc and DABNAc as potential agents against Tay-Sachs and Sandhoff disease.
gan: Rountree, J, et al.
Cyhoeddwyd: (2009)

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
gan: Scott, D, et al.
Cyhoeddwyd: (1999)

Mirror image mimics of rhamnose fucose galactose and mannose
gan: Shilvock, J, et al.
Cyhoeddwyd: (1997)

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
gan: Shilvock, J, et al.
Cyhoeddwyd: (1999)

Enantiomeric hexosaminidase inhibitors
gan: Rountree, J, et al.
Cyhoeddwyd: (2005)

Synthesis and biological characterisation of novel N-alkyl-deoxynojirimycin alpha-glucosidase inhibitors.
gan: Rawlings, A, et al.
Cyhoeddwyd: (2009)

Homochiral carbon branched piperidines from carbon branched sugar lactones: 4-C-methyl-deoxyfuconojirimycin (DFJ) and its enantiomer - removal of glycosidase inhibition
gan: Hotchkiss, D, et al.
Cyhoeddwyd: (2007)

L-(+)-swainsonine and other pyrrolidine inhibitors of naringinase: Through an enzymic looking glass from D-mannosidase to L-rhamnosidase?
gan: Davis, B, et al.
Cyhoeddwyd: (1996)

Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application
gan: Asano, N, et al.
Cyhoeddwyd: (2000)

Enantiomeric 2-acetamido-1,4-dideoxy-1,4-iminoribitols as potential pyrrolidine hexosaminidase inhibitors
gan: Rountree, J, et al.
Cyhoeddwyd: (2011)

Molecular requirements of imino sugars for the selective control of N-linked glycosylation and glycosphingolipid biosynthesis
gan: Butters, T, et al.
Cyhoeddwyd: (2000)

Improved cellular inhibitors for glycoprotein processing alpha-glucosidases: biological characterisation of alkyl- and arylalkyl-N-substituted deoxynojirimycins
gan: Alonzi, D, et al.
Cyhoeddwyd: (2009)

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
gan: Ardron, H, et al.
Cyhoeddwyd: (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
gan: Hakansson, A, et al.
Cyhoeddwyd: (2007)

DELTA-LACTAMS - SYNTHESIS FROM D-GLUCOSE, AND PRELIMINARY EVALUATION AS A FUCOSIDASE INHIBITOR, OF L-FUCONIC-DELTA-LACTAM
gan: Fleet, G, et al.
Cyhoeddwyd: (1988)

Sugar amino acids at the anomeric position of carbohydrates: synthesis of spirocyclic amino acids of 6-deoxy-L-lyxofuranose
gan: Bleriot, Y, et al.
Cyhoeddwyd: (2006)

Iminosugar inhibitors for treating the lysosomal glycosphingolipidoses
gan: Butters, T, et al.
Cyhoeddwyd: (2005)

Imino sugar inhibitors for treating the lysosomal glycosphingolipidoses.
gan: Butters, T, et al.
Cyhoeddwyd: (2005)

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
gan: Mercer, T, et al.
Cyhoeddwyd: (2009)

Mimics of galactofuranose and galactopyranose
gan: Fleet, G, et al.
Cyhoeddwyd: (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
gan: Shilvock, J, et al.
Cyhoeddwyd: (1998)

Looking-glass synergistic pharmacological chaperones: DGJ and L-DGJ from the enantiomers of tagatose.
gan: Jenkinson, S, et al.
Cyhoeddwyd: (2011)

Glycolipids in cell biology and medicine - Introduction
gan: Dwek, R, et al.
Cyhoeddwyd: (2003)

Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin - is the mode of action by modification of N-linked glycoproteins?
gan: Martin, A, et al.
Cyhoeddwyd: (1999)

Stereospecific synthesis of spirohydantoins of beta-glucopyranose: Inhibitors of glycogen phosphorylase
gan: Krulle, T, et al.
Cyhoeddwyd: (1997)

Synthesis of a novel AB4 monomer and its incorporation into highly branched dendritic structures.
gan: Scott, D, et al.
Cyhoeddwyd: (1999)

Preparation, biochemical characterization and biological properties of radiolabelled N-alkylated deoxynojirimycins.
gan: Mellor, H, et al.
Cyhoeddwyd: (2002)

Novel mannosidase inhibitors probe glycoprotein degradation pathways in cells.
gan: Butters, T, et al.
Cyhoeddwyd: (2009)

Bis(1,3-dihydroxy-isopropyl)amine (BDI) as an AB(4) dendritic building block: rapid synthesis of a second generation dendrimer
gan: Scott, D, et al.
Cyhoeddwyd: (2000)

N-butyldeoxygalactonojirimycin: a more selective inhibitor of glycosphingolipid biosynthesis than N-butyldeoxynojirimycin, in vitro and in vivo.
gan: Andersson, U, et al.
Cyhoeddwyd: (2000)

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
gan: Best, D, et al.
Cyhoeddwyd: (2010)

Design and synthesis of acetamido tri- and tetra-hydroxyazepanes: potent and selective beta-N-acetylhexosaminidase inhibitors.
gan: Li, H, et al.
Cyhoeddwyd: (2009)

Looking Glass
gan: Nur Mariyah Muhamad Afandi
Cyhoeddwyd: (2020)

Strategy for designing selective α-L-rhamnosidase inhibitors: Synthesis and biological evaluation of DMDP cyclic isothioureas
gan: Miyawaki, S, et al.
Cyhoeddwyd: (2016)