Abstract
The synthesis of the methyl α- and β-N-dansyl-d-galactosaminides is described using methyl α,β-2-azido-2-deoxy-d-galactopyranoside as starting material. This was reduced to the corresponding methyl α,β-2-amino-2-deoxy-d-galactopyranoside and then treated with dansyl chloride to yield a mixture of methyl α,β-N-dansyl-d-galactosaminides which was separated into individual anomeric forms by flash chromatography on silica gel. Methyl α-N-dansyl-d-galactosaminide was used as a fluorescent indicator ligand in continuous substitution titrations to determine the association constants of nonchromophoric carbohydrates with theN-acetyl-d-galactosamine specific lectin fromErythrina corallodendron.
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Abbreviations
- ECorL:
-
Erythrina corallodendron lectin
- MeαGalNDns:
-
methyl 2-deoxy-2-(5-dimethylamino-1-naphthalenesulfamido)-α-d-galactopyranoside
- MeβGalNDns:
-
methyl 2-deoxy-2-(5-dimethylamino-1-naphthalenesulfamido)-β-d-galactopyranoside
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Dedicated to Hilde De Boeck (1958–1991).
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Kinzy, W.R., Belenky, D.M., Loontiens, F.G. et al. Synthesis of methyl α- and β-N-dansyl-d-galactosaminides, probes for the combining sites ofN-acetyl-d-galactosamine-specific lectins. Glycoconjugate J 9, 225–227 (1992). https://doi.org/10.1007/BF00731133
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DOI: https://doi.org/10.1007/BF00731133