Synthesis of 7-O-(2-deoxy-2-sulfamido-alpha-D-glucopyranosyl)-4-methylcoumarin sodium salt: a fluorogenic substrate for sulfamidase.
The title compound, useful for testing the efficacy of heparin sulfamidase, was synthesized in good yield starting from 2-azido-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranosyl fluoride, reducing the azido group efficiently with SnCl(2)-PhSH-Et(3)N reagent and finally crystallizing the N-sulfated product from methanol after deacetylation.
Dasgupta
Falguni
F
BioMarin Pharmaceutical Inc., 11 Pimentel Court, Novato, CA 94949, USA. fdcarbo@hotmail.com
Masada
R Irene
RI
D003374:Coumarins / Q000138:chemical synthesis*; D005456:Fluorescent Dyes; D006867:Hydrolases / Q000378:metabolism*; D009005:Monosaccharides / Q000138:chemical synthesis*; D009084:Mucopolysaccharidosis III / Q000378:metabolism; D013379:Substrate Specificity
C476485:7-O-(2-deoxy-2-sulfamido-alpha-D-glucopyranosyl)-4-methylcoumarin sodium salt; D003374:Coumarins; D005456:Fluorescent Dyes; D009005:Monosaccharides; D006867:Hydrolases; C022708:N-sulfoglucosamine sulfohydrolase