Amination of sugars

Amination of Sugar Derivatives with a Mixture of Phthalimide, Triphenylphos-phine, and Diethyl Azodicarboxylate, A. Zamojski, W. A. Szarek, and J. K. N. Jones, Carbohydr. Res., 23 (1972) 460-462. 

Carbohydrates show very low ultraviolet (UV) absorption. Their visualization and evaluation on TLC plates can be satisfactorily made only after suitable derivatization. The majority of chemical derivatization procedures are based on the reductive properties of carbohydrates. Reductive amination of sugars in the presence of an acid is a typical example. Methods based on reductive amination require an aldehydic reducing carbon on the saccharide that reacts with the amino group of the chromophore or fluorophore. 

The following are some of the typical industrial applications for liquid-phase carbon adsorption. Generally liquid-phase carbon adsorbents are used to decolorize or purify liquids, solutions, and liquefiable materials such as waxes. Specific industrial applications include the decolorization of sugar syrups the removal of sulfurous, phenolic, and hydrocarbon contaminants from wastewater the purification of various aqueous solutions of acids, alkalies, amines, glycols, salts, gelatin, vinegar, fruit juices, pectin, glycerol, and alcoholic spirits dechlorination the removal of... 

A rather limited collection of simple precursor molecules is sufficient to provide for the biosynthesis of virtually any cellular constituent, be it protein, nucleic acid, lipid, or polysaccharide. All of these substances are constructed from appropriate building blocks via the pathways of anabolism. In turn, the building blocks (amino acids, nucleotides, sugars, and fatty acids) can be generated from metabolites in the cell. For example, amino acids can be formed by amination of the corresponding a-keto acid carbon skeletons, and pyruvate can be converted to hexoses for polysaccharide biosynthesis. 

It should be noted that liquefaction at times occurs because of eutectic formation (e.g., often with caffeine combinations) and that this may not necessarily be associated with decomposition. On the other hand, discoloration (e.g., amines and sugars) usually is. 

Immers, J and E. Vasseur Influence of Sugars and Amines on the Colori-... 

Another example of the ability of proteinogenic amino acids, small peptides, and amines to catalyse the formation of new C-C bonds has been demonstrated by Weber and Pizzarello they were able to carry out model reactions for the stereospecific synthesis of sugars (tetroses) using homochiral L-dipeptides. The authors achieved a D-enantiomeric excess (ee) of more than 80% using L-Val-L-Val as the peptide catalyst in sugar synthesis (in particular D-erythrose) via self-condensation of glycol aldehyde. 

Earlier studies showed that reactions of sugars with ammonia lead to small molecules such as amines or organic acids. A. L. Weber has reported important autocatalytic processes occurring when trioses are allowed to react with ammonia under anaerobic conditions, such reactions provide products which are autocatalyt-ically active. Their autocatalytic activity was determined directly by investigating their effect on an identical triose-ammonia reaction. Both an increase in the triose degradation rate and an increased rate of synthesis of pyruvate, the dehydration product of the triose, were observed. Such processes may have been of importance for prebiotic chemistry occurring on the primeval Earth (Weber, 2007). 

Two bases approaches are used in the synthesis of sugar carbamides direct interaction of carbohydrates with carbamides and their analogs in the conditions of acid catalysis (a) and interaction of acetylation N-glycosylisothiocyanates with amines (b) or interaction of acetylation N-glycosylamines with arylisothiocyanates (c) [3],... 

The authors in their works [21, 22] show that N-nitrozo derivative of carbohydrates can easily come into the reaction of substitution on carbonil group of N-aglicon witch the help of interaction of amines witch the development of sugar carbohydrate derivatives. 

Since then, optically active a-aminophosphonates have been obtained by a variety of methods including resolution, asymmetric phosphite additions to imine double bonds and sugar-based nitrones, condensation of optically active ureas with phosphites and aldehydes, catalytic asymmetric hydrogenation, and 1,3-dipolar cycloadditions. These approaches have been discussed in a comprehensive review by Dhawan and Redmore.9 More recent protocols involve electrophilic amination of homochiral dioxane acetals,10 alkylation of homochiral imines derived from pinanone11 and ketopinic acid,12 and alkylation of homochiral, bicyclic phosphonamides.13... 

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