title: Novel efficient routes to indoxyl glycosides for monitoring glycosidase activities.
abstract: A new efficient synthesis for broad access to indoxyl glycosides was developed. Indoxylic acid allyl ester linked to a sugar structure served as the key intermediate in this route. Selective ester cleavage and mild decarboxylation led to the corresponding indoxyl glycosides in good yields. This synthesis was applied for preparation of indoxyl glycosides of fucose, sialic acid, and 6'-sialyl lactose.
authors.affiliation: University of Hamburg , Faculty of Science, Department of Chemistry, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany.
authors.forename: Stephan
authors.initials: S
authors.lastname: Böttcher
authors.forename: Markus
authors.initials: M
authors.lastname: Hederos
authors.forename: Elise
authors.initials: E
authors.lastname: Champion
authors.forename: Gyula
authors.initials: G
authors.lastname: Dékány
authors.forename: Joachim
authors.initials: J
authors.lastname: Thiem
mesh_terms: D005643:Fucose / Q000737:chemistry*; D006026:Glycoside Hydrolases / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry; D006031:Glycosylation; D007211:Indoles / Q000737:chemistry*; D007785:Lactose / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000737:chemistry
chemical_list: C403777:6'-sialyllactose; D006027:Glycosides; D007211:Indoles; D005643:Fucose; C034082:indoxyl; D006026:Glycoside Hydrolases; D019158:N-Acetylneuraminic Acid; D007785:Lactose