Highly selective nitroxyl radical-mediated oxidation of primary alcohol groups in water-soluble glucans
article
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.
Chemicals/CAS: glucan, 9012-72-0, 9037-91-6; glucoside, 50986-29-3; pullulan, 9057-02-7; starch, 9005-25-8, 9005-84-9; trehalose, 99-20-7
Chemicals/CAS: glucan, 9012-72-0, 9037-91-6; glucoside, 50986-29-3; pullulan, 9057-02-7; starch, 9005-25-8, 9005-84-9; trehalose, 99-20-7
Topics
TNO Identifier
82493
ISSN
00086215
Source
Carbohydrate Research, 269(1), pp. 89-98.
Pages
89-98
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