Regioselectivity in sulfation of galactosides by sulfuric acid and dicyclohexylcarbodiimide.
Methyl alpha- and beta-D-galactopyranosides and 4-O-beta-D-galactopyranosyl-3,6-anhydro-L-galactose dimethylacetal were sulfated with sulfuric acid and dicyclohexylcarbodiimide as a condensation reagent. The sulfated sugars were isolated by ion-exchange chromatography, characterized, and assigned by methylation analyses. On the basis of the yield of each sulfated product that was isolated, sulfation on O-6 appeared to be predominant.
Department of Chemistry and Materials Technology, Faculty of Engineering and Design, Kyoto Institute of Technology, Japan.
R
R
Takano
T
T
Ueda
Y
Y
Uejima
K
K
Kamei-Hayashi
S
S
Hara
S
S
Hirase
D000080:Acetals / Q000737:chemistry / Q000378:metabolism; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000138:chemical synthesis / Q000302:isolation & purification; D002852:Chromatography, Ion Exchange; D004024:Dicyclohexylcarbodiimide / Q000737:chemistry*; D004187:Disaccharides / Q000737:chemistry / Q000378:metabolism; D008745:Methylation; D008756:Methylgalactosides / Q000737:chemistry* / Q000378:metabolism; D008969:Molecular Sequence Data; D013237:Stereoisomerism; D013431:Sulfates / Q000138:chemical synthesis* / Q000302:isolation & purification; D013464:Sulfuric Acids / Q000737:chemistry*
D000080:Acetals; D002241:Carbohydrates; D004187:Disaccharides; D008756:Methylgalactosides; D013431:Sulfates; D013464:Sulfuric Acids; C078116:4-O-galactopyranosyl-3,6-anhydrogalactose dimethylacetal; D004024:Dicyclohexylcarbodiimide; C033158:sulfuric acid