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Synthesis, analysis and reduction of 2-nitropropyl starch

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Author: Heeres, A. · Doren, H.A. van · Gotlieb, K.F. · Bleeker, I.P. · Bergsma, J. · Kellogg, R.M.
Type:article
Date:2001
Institution: Centraal Instituut voor Voedingsonderzoek TNO
Source:Carbohydrate Research, 2, 330, 191-204
Identifier: 87475
doi: doi:10.1016/S0008-6215(00)00288-3
Keywords: Nutrition · Amylose · Carbohydrate Sequence · Hydrogenation · Molecular Sequence Data · Nuclear Magnetic Resonance, Biomolecular · Oligosaccharides · Oxidation-Reduction · Plant Extracts · Solanum tuberosum · Starch · Solanum tuberosum

Abstract

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 3.2.1.1; Amylose, 9005-82-7; Oligosaccharides; Plant Extracts; Starch, 9005-25-8