Sulfo-protected hexosamine monosaccharides: potentially versatile building blocks for glycosaminoglycan synthesis.
2,2,2-Trifluorodiazoethane was investigated as a reagent for sulfo group protection on hexosamine monosaccharides. The synthesis of glucosamine and galactosamine building blocks fully differentiated for glycosaminoglycan synthesis and the synthesis of glycosyl donors are described. The compatibility of trifluoroethylsulfonate under a variety of reaction conditions has also been investigated. [structure: see text]
Karst
Nathalie A
NA
Departments of Chemistry, Biology and Chemical and Biological Engineering, Rensselaer Polytechnic Institute, Troy, NY 12180, USA.
Islam
Tasneem F
TF
Linhardt
Robert J
RJ
D001391:Azo Compounds / Q000737:chemistry; D002236:Carbohydrate Conformation; D005688:Galactosamine / Q000138:chemical synthesis; D005944:Glucosamine / Q000138:chemical synthesis; D006025:Glycosaminoglycans / Q000138:chemical synthesis*; D006595:Hexosamines / Q000737:chemistry*; D009005:Monosaccharides / Q000138:chemical synthesis*; D013463:Sulfuric Acid Esters / Q000737:chemistry*
D001391:Azo Compounds; D006025:Glycosaminoglycans; D006595:Hexosamines; D009005:Monosaccharides; D013463:Sulfuric Acid Esters; D005688:Galactosamine; D005944:Glucosamine