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Scalable syntheses of both enantiomers of DNJNAc and DGJNAc from glucuronolactone: the effect of N-alkylation on hexosaminidase inhibition.
TLDR
Correlation of the in vitro inhibition with the cellular data, by using a free oligosaccharide analysis of the lysosomal enzyme inhibition, revealed the following structure-property relationship: hydrophobic side-chains preferentially promoted the intracellular access of iminosugars to those inhibitors with more-hydrophilic side-chain characteristics. Expand
Synthesis of 2-acetamido-1,2-dideoxy-d-galacto-nojirimycin [DGJNAc] from d-glucuronolactone: the first sub-micromolar inhibitor of α-N-acetylgalactosaminidases
Abstract 2-Acetamido-1,2-dideoxy- d -galacto-nojirimycin [DGJNAc], prepared in 20% overall yield from d -glucuronolactone, is the first potent competitive sub-micromolar inhibitor ofExpand
3‐Hydroxyazetidine Carboxylic Acids: Non‐Proteinogenic Amino Acids for Medicinal Chemists
TLDR
An N‐methylazetidine amide derivative is a specific inhibitor of β‐hexosaminidases at the micromolar level, and is only the second example of potent inhibition of any glycosidase by an amide of a sugar amino acid related to an iminosugar. Expand
Nine of 16 stereoisomeric polyhydroxylated proline amides are potent β-N-acetylhexosaminidase inhibitors.
All 16 stereoisomeric N-methyl 5-(hydroxymethyl)-3,4-dihydroxyproline amides have been synthesized from lactones accessible from the enantiomers of glucuronolactone. Nine stereoisomers, including allExpand
Short and sweet: (D)-glucose to (L)-glucose and (L)-glucuronic acid.
TLDR
This work gives the definitive and cheap synthesis of 99.4% pure L-glucose from D- glucose which requires purification of neither intermediates nor final product other than extraction into and removal of solvents. Expand
Synthesis of the enantiomers of XYLNAc and LYXNAc: comparison of β-N-acetylhexosaminidase inhibition by the 8 stereoisomers of 2-N-acetylamino-1,2,4-trideoxy-1,4-iminopentitols.
TLDR
Both XYLNAc and LABNAc are potent inhibitors against HexNAcases and the N-benzyl derivatives are better inhibitors than the parent compounds. Expand
Synthesis from D-altrose of (5R,6R,7R,8S)-5,7-dihydroxy-8-hydroxymethylconidine and 2,4-dideoxy-2,4-imino-D-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-D-mannitol.
Ring closure of a 3,5-di-O-triflate derived from D-altrose with benzylamine allowed the formation of both monocyclic and bicyclic azetidine analogues of swainsonine.
An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic & thermodynamic azido-γ-lactones.
TLDR
Two epimeric azido-heptitols allow biotechnological transformations via Izumoring techniques to 8 of the 16 possible homonojirimycin analogues, 5 of which were isolated pure because of the lack of stereoselectivity of the final reductive amination. Expand
Structural essentials for β-N-acetylhexosaminidase inhibition by amides of prolines, pipecolic and azetidine carboxylic acids.
This paper explores the computer modelling aided design and synthesis of β-N-acetylhexosaminidase inhibitors along with their applicability to human disease treatment through biological evaluation inExpand
1,2:3,4-Di- O -isopropylidene-- D -psicofuranose
The crystal structure of the title diacetone psicose, C12H20O6, establishes the stereochemistry of the anomeric spiro­acetal 1,2:3,4-di-O-isopropyl­idene-β-d-psicofuran­ose. The structure consists ofExpand
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