Highly selective nitroxyl radical-mediated oxidation of primary alcohol groups in water-soluble glucans
With catalytic amounts of 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and hypochlorite/bromide as the regenerating oxidant in water, primary alcohol groups in glucans and derivatives thereof were rapidly and completely oxidised. For pyranosides, selectivity was higher than 95% and no side products...
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Published in | Carbohydrate research Vol. 269; no. 1; pp. 89 - 98 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Elsevier Ltd
03.04.1995
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Subjects | |
Online Access | Get full text |
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Summary: | With catalytic amounts of 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and hypochlorite/bromide as the regenerating oxidant in water, primary alcohol groups in glucans and derivatives thereof were rapidly and completely oxidised. For pyranosides, selectivity was higher than 95% and no side products could be detected with
1H and
13C NMR or with high-performance anion-exchange chromatography (HPAEC). The optimum pH for the reaction was between 10 and 11. The oxidation was found to be first order in TEMPO and Br
−. The oxidation method can be applied to determine the amount of primary alcohol groups in water-soluble glucans; for pullulan, a proportion of 70% and for dextran, a proportion of 3% primary alcohol groups was found. |
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ISSN: | 0008-6215 1873-426X |
DOI: | 10.1016/0008-6215(94)00343-E |