title: Synthesis of methyl alpha- and beta-N-dansyl-D-galactosaminides, probes for the combining sites of N-acetyl-D-galactosamine-specific lectins.
abstract: The synthesis of the methyl alpha- and beta-N-dansyl-D-galactosaminides is described using methyl alpha,beta-2-azido-2-deoxy-D-galactopyranoside as starting material. This was reduced to the corresponding methyl alpha,beta-2-amino-2-deoxy-D-galactopyranoside and then treated with dansyl chloride to yield a mixture of methyl alpha,beta-N-dansyl-D-galactosaminides which was separated into individual anomeric forms by flash chromatography on silica gel. Methyl alpha-N-dansyl-D-galactosaminide was used as a fluorescent indicator ligand in continuous substitution titrations to determine the association constants of nonchromophoric carbohydrates with the N-acetyl-D-galactosamine specific lectin from Erythrina corallodendron.
authors: Department of Membrane Research and Biophysics, Weizmann Institute of Science, Rehovot, Israel.
authors: W R
authors: WR
authors: Kinzy
authors: D M
authors: DM
authors: Belenky
authors: F G
authors: FG
authors: Loontiens
authors: N
authors: N
authors: Sharon
mesh_terms: D000116:Acetylgalactosamine / Q000378:metabolism*; D003619:Dansyl Compounds / Q000138:chemical synthesis*; D005688:Galactosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D037102:Lectins / Q000378:metabolism*; D015335:Molecular Probes; D015394:Molecular Structure; D011485:Protein Binding; D012680:Sensitivity and Specificity; D013050:Spectrometry, Fluorescence
chemical_list: D003619:Dansyl Compounds; D037102:Lectins; D015335:Molecular Probes; C079425:methyl-N-dansylgalactosaminide; D005688:Galactosamine; D000116:Acetylgalactosamine