Synthesis, analysis and reduction of 2-nitropropyl starch.
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 alpha-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).
Heeres
A
A
TNO Nutrition and Food Research Institute, Zeist, The Netherlands.
van Doren
H A
HA
Gotlieb
K F
KF
Bleeker
I P
IP
Bergsma
J
J
Kellogg
R M
RM
D000688:Amylose / Q000737:chemistry; D002240:Carbohydrate Sequence; D006865:Hydrogenation; D008969:Molecular Sequence Data; D019906:Nuclear Magnetic Resonance, Biomolecular; D009844:Oligosaccharides / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010936:Plant Extracts; D011198:Solanum tuberosum; D013213:Starch / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D000516:alpha-Amylases / Q000378:metabolism
D009844:Oligosaccharides; D010936:Plant Extracts; D013213:Starch; D000688:Amylose; D000516:alpha-Amylases