Sugar analogs nitrogen

SCHEME 9.3 T3fpical S3fnthetic approaches to sugar analogs with nitrogen in the ring. 

Nitrogen-containing sugar analogs have recently been described fi-om several Fabaceae species. One of them, 2-5-dihydroxymethyl-3,4-hydroxypyrrolidine (DMDP), was first isolated form leaves and roots of Derris elliptica (10). These sugar mimics were shown to be powerfid glucosidadse inhibitors (11). DMDP acts as an antifeedant for locusts and is toxic for certain caterpillars and beetles. It was isolated in our laboratory fi-om the roots of Derris urucu (Mathias, L. Parente, J. P., unpublished data.)... 

M. Berthelot. found that many nitrogenous organic compounds furnish ammonia when heated with hydriodic acid and J. Kjeldahl showed that the nitrogen of many nitrogenous compounds is all converted into ammonia or ammonium sulphate when heated with cone, sulphuric acid—in the case of nitro-eompounds and cyanides the reaction is not always quantitative. The reaction proceeds more satisfactorily in the presence of mercury or mercuric oxide, copper, potassium hydrosulphate, sugar, phenol, benzoic acid, and analogous compounds. This reaction has been discussed by C. Arnold, A. Atterberg, C. Budde and C. V. Sehon,... 

Numerous derivatives of 2-amino-2-deoxy-D-glucosyl halides have been reported recently, especially by Micheel and coworkers.112 113 150 163 168 Methods of synthesis are similar to those for the analogous non-nitrogeneous sugars, namely, treatment of acylated derivatives with acyl halides,169 hydrogen halides,106 1U-112 147 149 or titanic halide.106... 

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