Synthesis of α- and β-d-glucopyranosyl triazoles by CuAAC 'click chemistry': reactant tolerance, reaction rate, product structure and glucosidase inhibitory properties

Carbohydrate Research

Volumn 345, Issue 9, 2010, Pages 1123-1134

  Dedola, Simone ^a   Hughes, David L ^b   Nepogodiev, Sergey A ^a   Rejzek, Martin ^a   Field, Robert A ^a  

^a JOHN INNES CENTRE   (United Kingdom)

^b UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

d Glucopyranosyl azide reactivity; Click chemistry; Glucosidase inhibitor; Microwave; Triazole

Indexed keywords

ANOMERIC CONFIGURATION; ANOMERS; AZIDO GROUP; CLICK CHEMISTRY; COMPETITION REACTIONS; CRYSTALLOGRAPHIC DATA; DIPOLAR CYCLOADDITIONS; GLUCOSIDASE; GLYCOSIDASE INHIBITORS; PERPENDICULAR ORIENTATION; PRODUCT STRUCTURE; STRUCTURAL STUDIES; TRIAZOLE RING;

ACETYLENE; CYCLOADDITION; NITROGEN COMPOUNDS; REACTION RATES; SUGAR (SUCROSE); SYNTHESIS (CHEMICAL);

ENZYME INHIBITION;

1 (2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GLUCOPYRANOSYL) 4 (TERT BUTYL OXYCARBONYLAMINOMETHYL) [1,2,3] TRIAZOLE; 1 (2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GLUCOPYRANOSYL) 4 BENZHYDRYLOXYMETHYL [1,2,3] TRIAZOLE; 1 (2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GLUCOPYRANOSYL) 4 HYDROXYMETHYL [1,2,3] TRIAZOLE; 1 (2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GLUCOPYRANOSYL) 4 METHYLOXYCARBONYL [1,2,3] TRIAZOLE; 1 (2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GLUCOPYRANOSYL) 4 PHENYL [1,2,3] TRIAZOLE; 1 (2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL) 4 (TERT BUTOXYCARBONYL AMINOMETHYL) [1,2,3] TRIAZOLE; 1 (2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL) 4 BENZHYDRYLOXYMETHYL [1,2,3] TRIAZOLE; 1 (2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL) 4 HYDROXYMETHYL [1,2,3] TRIAZOLE; 1 (2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL) 4 METHOXYCARBONYL [1,2,3] TRIAZOLE; 1 (2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL) 4 PHENYL [1,2,3] TRIAZOLE; 1 (ALPHA DEXTRO GLUCOPYRANOSYL) 4 (TERT BUTYL OXYCARBONYLAMINOMETHYL) [1,2,3] TRIAZOLE; 1 (ALPHA DEXTRO GLUCOPYRANOSYL) 4 CARBOXYMETHYL [1,2,3] TRIAZOLE; 1 (ALPHA DEXTRO GLUCOPYRANOSYL) 4 HYDROXYMETHYL [1,2,3] TRIAZOLE; 1 (ALPHA DEXTRO GLUCOPYRANOSYL) 4 METHYL BENZHYDRYLOXYMETHYL [1,2,3] TRIAZOLE; 1 (ALPHA DEXTRO GLUCOPYRANOSYL) 4 PHENYL [1,2,3] TRIAZOLE; 1 (BETA DEXTRO GLUCOPYRANOSYL) 4 (TERT BUTYLOXYCARBONYLAMINOMETHYL) [1,2,3] TRIAZOLE; 1 (BETA DEXTRO GLUCOPYRANOSYL) 4 AMINOMETHYL [1,2,3] TRIAZOLE; 1 (BETA DEXTRO GLUCOPYRANOSYL) 4 CARBOXY [1,2,3] TRIAZOLE; 1 (BETA DEXTRO GLUCOPYRANOSYL) 4 HYDROXYMETHYL [1,2,3] TRIAZOLE; 1 (BETA DEXTRO GLUCOPYRANOSYL) 4 METHOXYCARBONYL [1,2,3] TRIAZOLE; 1 (BETA DEXTRO GLUCOPYRANOSYL) 4 METHYL BENZHYDRYLOXYMETHYL [1,2,3] TRIAZOLE; 1 (BETA DEXTRO GLUCOPYRANOSYL) 4 PHENYL [1,2,3] TRIAZOLE; ALPHA DEXTRO GLUCOPYRANOSYL TRIAZOLE; ALPHA GLUCOSIDASE; BETA DEXTRO GLUCOPYRANOSYL TRIAZOLE; BETA GLUCOSIDASE; GLUCOPYRANOSYL TRIAZOLE; GLYCOSIDASE INHIBITOR; PROP 2 YNYLOXYDIPHENYLMETHANE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ALKYNE; AZIDE; COPPER; ENZYME INHIBITOR; GLUCOSIDASE; TRIAZOLE DERIVATIVE;

ALMOND; ARTICLE; CHEMICAL BOND; CYCLOADDITION; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INHIBITION; ENZYME KINETICS; ENZYME STRUCTURE; ENZYME SYNTHESIS; ISOMER; PRIORITY JOURNAL; SOLID STATE; X RAY CRYSTALLOGRAPHY; YEAST; ANTAGONISTS AND INHIBITORS; CATALYSIS; CHEMISTRY; ENZYMOLOGY; KINETICS; PRUNUS; STEREOISOMERISM; SYNTHESIS;

ALKYNES; AZIDES; CATALYSIS; COPPER; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; GLUCOSIDASES; KINETICS; PRUNUS; STEREOISOMERISM; TRIAZOLES;

EID: 77953156257     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2010.03.041     Document Type: Article

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