A5013717018- Carbohydrate Chemistry and Synthesis
- Glycosylation and Glycoproteins Research
- Chemical Synthesis and Analysis
- Lysosomal Storage Disorders Research
- Synthetic Organic Chemistry Methods
- Enzyme Production and Characterization
- Chemical Synthesis and Reactions
- Fluorine in Organic Chemistry
- Polyamine Metabolism and Applications
- Trypanosoma species research and implications
- Enzyme Catalysis and Immobilization
- Legume Nitrogen Fixing Symbiosis
- Diet, Metabolism, and Disease
- Synthesis and Catalytic Reactions
- Biochemical and Molecular Research
- Synthesis of Organic Compounds
- Organophosphorus compounds synthesis
- Microbial Metabolites in Food Biotechnology
- Crystallization and Solubility Studies
- Cyclopropane Reaction Mechanisms
- Synthesis and Biological Evaluation
- X-ray Diffraction in Crystallography
- Synthesis and Biological Activity
- Synthesis and Reactions of Organic Compounds
- Peptidase Inhibition and Analysis
Université d'Orléans
2011-2023
Centre National de la Recherche Scientifique
2011-2023
Institut de Chimie Organique et Analytique
2012-2023
Université de Rouen Normandie
2015
Laboratoire COBRA
2015
Université de Strasbourg
2011
Bar-Ilan University
2011
Hokuriku University
2009
Jagiellonian University
2009
State University of New York
1996-2006
Fabry disease is a lysosomal storage disorder caused by deficient alpha-galactosidase A (alpha-Gal A) activity. Deficiency of the enzyme activity results in progressive deposition neutral glycosphingolipids with terminal alpha-galactosyl residue vascular endothelial cells. We recently proposed chemical chaperone therapy for this administration 1-deoxygalactonojirimycin, potent inhibitor enzyme, at subinhibitory intracellular concentrations [Fan, J.-Q., Ishii, S., Asano, N. and Suzuki, Y....
Remove to improve. Removal of the hydroxymethyl groups in 1 give 2 significantly enhances inhibitory potency towards glucosylceramide β-glucosidase (GCase) and abolishes inhibition α-glucosidases. Xylitol doubles residual activity GCase fibroblasts from Gaucher patients at subinhibitory concentration (10 nM). This compound is therefore a promising candidate for development small-molecule drugs treatment Gaucher's disease without side effects associated with α-glucosidase inhibition.
Abstract A series of O ‐alkyl iminoxylitol derivatives was synthesized and evaluated as β‐glucocerebrosidase (GCase) inhibitors. This structure–activity study shows a dramatic influence the position alkyl chain (α‐C1, O2, O3, or O4) on human GCase inhibition. Remarkably, 1,2‐shift from C1 to O2 found maintain high inhibitory potency toward well chaperone activity at sub‐inhibitory concentration (10 n M ). Removal stereogenic center pseudo‐anomeric led shorter more practical synthetic...
Mycobacterium tuberculosis modulates host immune responses through proteins and complex glycolipids. Here, we report that the glycosylphosphatidylinositol anchor phosphatidyl-myo-inositol hexamannosides PIM(6) or PIM(2) exert potent anti-inflammatory activities. PIM strongly inhibited Toll-like receptor (TLR4) myeloid differentiation protein 88 (MyD88)-mediated release of NO, cytokines, chemokines, including tumor necrosis factor (TNF), interleukin 12 (IL-12) p40, IL-6, keratinocyte-derived...
The synthesis of a UDP-Galf analog incorporating 1,4-dideoxy-1,4-imino-d-galactitol skeleton alpha-linked to UMP by 3C-tether and series related pyrrolidine galactofuranose mimicks is reported. These compounds were obtained way the highly stereoselective reaction silylated nucleophiles with N-Cbz glucofuranosylamine which afforded corresponding open-chain product 1,2-syn stereochemistry, as predicted from pionneering studies Kobayashi. Cyclization these intermediates alpha-C-glycosides...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis and conformational studies of .beta.-(1.fwdarw.6)- .beta.,.beta.-(1.fwdarw.1)-linked C-disaccharidesOlivier R. Martin Wen LaiCite this: J. Org. Chem. 1993, 58, 1, 176–185Publication Date (Print):January 1993Publication History Published online1 May 2002Published inissue 1 January 1993https://pubs.acs.org/doi/10.1021/jo00053a033https://doi.org/10.1021/jo00053a033research-articleACS PublicationsRequest reuse permissionsArticle...
The first example of the formation a seven-membered ring by way intramolecular-catalyzed amination saturated C−H bonds is reported (Du Bois reaction). influence various structural parameters was studied, and it shown that unexpected regioselectivity observed in nitrogen-containing systems could be rationalized conformational factors. These results open to innovative strategies for general synthesis polyfunctionalized piperidines.
An efficient and versatile strategy for the synthesis of nojirimycin C-glycosides related compounds with full stereocontrol is reported. The key steps process are addition organometallic reagents onto an l-sorbose-derived imine (13) followed by internal reductive amination. step, which controls α- vs β-configuration at pseudoanomeric center in final product, highly diastereoselective (re-face addition), stereoselectivity can be effectively inverted adding external monodentate Lewis acid...
Tetra-O-benzyl-d-glucofuranose was converted into uridine diphosphono-β-Galf mimics based on an iminosugar skeleton linked to UMP by a 2-hydroxypropyl tether. The synthesis is the highly regio- and stereoselective cycloaddition of original uridin-5'-yl allylphosphonate with 1,4-dideoxy-1,4-iminogalactitol-derived cyclic nitrone, followed reductive elaboration product. resulting iminogalactose−UMP conjugates are novel sugar nucleotide which could be useful as inhibitors UDP-Gal mutase...
α-Cyclodextrin was transformed in a cationic unit after per substitution with histidine (His-α-CD) and lysine (Lys-α-CD) molecules on the primary face. His-α-CD Lys-α-CD were used to form electrostatic complexes (CDplexes) plasmid DNA encoding luciferase gene, ability of CDplexes transfect mammalian cells examined using HEK293-T7 cells. The activity transfected His-α-CDplexes 8-fold higher than that obtained Lys-α-CDplexes. When transfection carried out presence chloroquine, Lys-α-CDplexes...
Abstract Difluoromethylated arenes are scaffolds of great interest. We report herein a mild and general method for the introduction CF 2 PO(OEt) moiety into arenes. The CuCF species, which is generated in situ from corresponding silylated derivatives, combination with aryl diazonium salts furnished highly valuable difluoromethylphosphonates moderate to good yields. This represents first introduce under conditions.
beta-Homonojirimycin (2) was prepared by the highly stereoselective double reductive amination of a 2,6-heptodiulose derivative (6 or 13) using ammonium formate and NaBH(3)CN. The process unsuccessful with primary amines. synthesis N-butyl-beta-homonojirimycin (19) achieved N-butanoylation 2 followed reduction resulting tertiary amide. Compound 19 found to be completely devoid anti-HIV activity, in marked contrast N-butyl-1-deoxynojirimycin. coupling 1-O-p-toluenesulfonyl 2, compound 20,...
Cross-metathesis reactions of α-1-C-allyl-1-deoxynojirimycin derivatives 7a,b and various functionalized alkenes mediated by Grubbs's catalyst 3 are reported. The showed reasonable to very good yields excellent E/Z selectivity. This methodology allows the efficient convergent synthesis iminosugar C-glycosides with a great degree structural diversity in aglycone, opening way variety new glycoconjugate mimetics biological interest.