Title
Synthesis, analysis and reduction of 2-nitropropyl starch
Author
Heeres, A.
van Doren, H.A.
Gotlieb, K.F.
Bleeker, I.P.
Bergsma, J.
Kellogg, R.M.
Centraal Instituut voor Voedingsonderzoek TNO
Publication year
2001
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
Subject
Nutrition
Amylose
Carbohydrate Sequence
Hydrogenation
Molecular Sequence Data
Nuclear Magnetic Resonance, Biomolecular
Oligosaccharides
Oxidation-Reduction
Plant Extracts
Solanum tuberosum
Starch
Solanum tuberosum
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DOI
https://doi.org/10.1016/s0008-6215(00)00288-3
TNO identifier
87475
ISSN
0008-6215
Source
Carbohydrate Research, 330 (2), 191-204
Document type
article