Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 33-43 |
| Journal | Carbohydrate polymers |
| Volume | 42 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2000 |
Cite this
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Synthesis and reduction of 2-nitroalkyl polysaccharide ethers. / Heeres, A.; Spoelma, F. F.; Van Doren, H. A.; Gotlieb, K. F.; Kellogg, R. M.; Bleeker, Ido Pieter.
In: Carbohydrate polymers, Vol. 42, No. 1, 2000, p. 33-43.Research output: Contribution to journal › Article › Academic › peer-review
TY - JOUR
T1 - Synthesis and reduction of 2-nitroalkyl polysaccharide ethers
AU - Heeres, A.
AU - Spoelma, F. F.
AU - Van Doren, H. A.
AU - Gotlieb, K. F.
AU - Kellogg, R. M.
AU - Bleeker, Ido Pieter
PY - 2000
Y1 - 2000
N2 - Several 2-nitroalkyl polysaccharide ethers (from pullulan (1), guar (2), agarose (3), inulin (4), cellulose (5), Na-α-polyglucuronate (6) and hydroxyethyl cellulose (7)) were synthesized by reaction with 2-nitro-1-alkenes (2-nitro-1-propene and 2-nitro-1-butene) formed in situ from 2-nitroalkyl acetates. Moderate to high efficiencies are obtained in concentrated aqueous solution/suspension for addition to 1-4 and 7. Analysis of this new class of polysaccharide derivatives with the aid of labeled 2-nitropropyl-2-13C pullulan revealed that the nitrogroup is a mixture of the nitroalkane and nitronic acid tautomers. Grafting of nitroalkenes is observed and, to a lesser extent, additional reactions of the nitro group (formation of carbonyl, oxime and allyl groups) take place. Reduction of 2-nitroalkyl polysaccharide ethers with Na2S2O4or Na2S2O4/NaBH4leads to complex polysaccharide ethers. The products obtained are most likely mixtures of starting material, nitroso compounds, hydroxylamines, hydroxypropyl ethers and sulfamates.
AB - Several 2-nitroalkyl polysaccharide ethers (from pullulan (1), guar (2), agarose (3), inulin (4), cellulose (5), Na-α-polyglucuronate (6) and hydroxyethyl cellulose (7)) were synthesized by reaction with 2-nitro-1-alkenes (2-nitro-1-propene and 2-nitro-1-butene) formed in situ from 2-nitroalkyl acetates. Moderate to high efficiencies are obtained in concentrated aqueous solution/suspension for addition to 1-4 and 7. Analysis of this new class of polysaccharide derivatives with the aid of labeled 2-nitropropyl-2-13C pullulan revealed that the nitrogroup is a mixture of the nitroalkane and nitronic acid tautomers. Grafting of nitroalkenes is observed and, to a lesser extent, additional reactions of the nitro group (formation of carbonyl, oxime and allyl groups) take place. Reduction of 2-nitroalkyl polysaccharide ethers with Na2S2O4or Na2S2O4/NaBH4leads to complex polysaccharide ethers. The products obtained are most likely mixtures of starting material, nitroso compounds, hydroxylamines, hydroxypropyl ethers and sulfamates.
U2 - 10.1016/S0144-8617(99)00123-X
DO - 10.1016/S0144-8617(99)00123-X
M3 - Article
VL - 42
SP - 33
EP - 43
JO - Carbohydrate polymers
JF - Carbohydrate polymers
SN - 0144-8617
IS - 1
ER -