Synthesis of methyl alpha- and beta-N-dansyl-D-galactosaminides, probes for the combining sites of N-acetyl-D-galactosamine-specific lectins.
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.
Kinzy
W R
WR
Department of Membrane Research and Biophysics, Weizmann Institute of Science, Rehovot, Israel.
Belenky
D M
DM
Loontiens
F G
FG
Sharon
N
N
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
D003619:Dansyl Compounds; D037102:Lectins; D015335:Molecular Probes; C079425:methyl-N-dansylgalactosaminide; D005688:Galactosamine; D000116:Acetylgalactosamine