Synthesis, analysis and reduction of 2-nitropropyl starch
van Doren, H.A.
Centraal Instituut voor Voedingsonderzoek TNO
Granular 2-nitropropyl potato starch was synthesized by reaction with 2-nitropropyl acetate in an aqueous suspension. Nitroalkylation occurs preferentially with the amylose fraction of potato starch, as was confirmed by leaching experiments and digestion of the modified starch with α-amylase. The 2-nitropropyl substituent is a mixture of the nitroalkane and nitronic acid tautomer. Some grafting occurs and to a lesser extent additional reactions (formation of carbonyls and oximes) of the nitro group take place. After catalytic hydrogenation of water soluble 2-nitropropyl starch only a small amount of the nitro functionality was reduced to the corresponding amine. Reduction of granular 2-nitropropyl starch with sodium dithionite did not go to completion and led to a complex mixture of starting material, several intermediates and side products (for example sulfamates). © 2001 Elsevier Science Ltd. Chemicals/CAS: alpha-Amylase, EC 220.127.116.11; Amylose, 9005-82-7; Oligosaccharides; Plant Extracts; Starch, 9005-25-8
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Molecular Sequence Data
Nuclear Magnetic Resonance, Biomolecular
Carbohydrate Research, 330 (2), 191-204