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Stereoselective synthesis of the trisaccharide moiety of ganglioside HLG-2
- Source :
- The Journal of organic chemistry. 79(2)
- Publication Year :
- 2013
-
Abstract
- The glycan portion of ganglioside HLG-2, which was identified in the extracts of the sea cucumber Holothuria leucospilota , was synthesized in a highly efficient and stereoselective manner. The unusual sequence of the trisaccharide moiety, α-N-glycolylsialyl-(2,4)-α-N-acetylsialyl-(2,6)-glucoside, was assembled by stereoselective coupling of a 5-N,4-O-carbonyl-protected sialyl phosphate donor, a N-2,2,2-trichloroethoxycarbonyl (Troc)-protected sialyl acceptor, and a (trimethylsilyl)ethyl-β-glucosyl acceptor in high yield. The synthesis featured the high-yielding construction of two α-sialyl linkages.
- Subjects :
- chemistry.chemical_classification
Glycan
Ganglioside
biology
Trimethylsilyl
Stereochemistry
Organic Chemistry
Molecular Sequence Data
Stereoisomerism
Holothuria leucospilota
biology.organism_classification
carbohydrates (lipids)
chemistry.chemical_compound
chemistry
Carbohydrate Sequence
Gangliosides
biology.protein
Carbohydrate Conformation
Moiety
Carbohydrate conformation
Trisaccharide
Subjects
Details
- ISSN :
- 15206904
- Volume :
- 79
- Issue :
- 2
- Database :
- OpenAIRE
- Journal :
- The Journal of organic chemistry
- Accession number :
- edsair.doi.dedup.....d404b6a0fd097c83ba7360999f1f581d