The phenyl - and -L-idopyranosiduronic acids and some other aryl glycopyranosiduronic acids |
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Authors: | R B Friedman B Weissmann |
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Institution: | Department of Biological Chemistry, University of Illinois, College of Medicine, Chicago, Illinois 60612 U.S.A. |
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Abstract: | Condensation of 1,2,3,4,6-penta-O-acetyl-á-l-idopyranose (1) with phenol yielded phenyl 2,3,4,6-tetra-O-acetyl-α- (2) and α-l-idopyranoside (4). Deacetylation of 2 and 4 afforded phenyl α and β-l-idopyranosides (3 and 5), respectively, the structures of which were verified by periodate oxidation studies. A platinum-catalyzed oxidation of 3 and 5 produced the amorphous phenyl α- and β-L-idopyranosiduronic acids (9 and 11), respectively, which were isolated as the crystalline cyclohexylammonium salts. Phenyl β- and α-d-glucopyranosiduronic acids are apparent minor byproducts of the catalytic oxidations, resulting from an inversion at C-5. p-Nitrophenyl α-d-mannopyranosiduronic acid and p-nitrophenyl α- and β-d-galactopyranosiduronic acids are also described. |
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