Amines reactions with sugars

Sugars are reactive molecules. Their reaction with amines, R—NH2, is of particular importance to us. Proteins possess a number of amino groups, one at the N-terminus of the protein and one for each lysine residue in the protein. There is a lot of sugar floating around in the human body. So it should not surprise us that there is nonspecific reaction of these sugars with proteins. These reactions are generally slow but they do occur sufficiently fast to be important. 

In a series of publications and patents,63 64 66"79 Wieniawski and coworkers reported the results of investigations of the reaction of sugar isothiocyanates with amines and various substituted hydrazides of heterocyclic acids. The reaction of isothiocyanate 2 with 2,6-diaminopyridine 81 was described,63 and the formation of dithioureide 82 as the sole product was observed. The... 

Reaction of thiolactams, in the sugar series, with amines allows the preparation of amidines which were desired for evaluation as glycosidase inhibitors [154]. 

Erickson, J. G. Reactions of Long Chain Amines. V. Reactions with Sugars. 

Thioureas are most commonly prepared from reaction of isothiocyanates with amines. Also there are some reports on reactions of anime or carbodiimides with several thionating reagents. AA -Disubstituted thioureas bearing double NH groups have been developed as sensors, and as catalysts because of their hydrogen bonding ability. A,A -Disubstituted thiourea-linked sugar chains have been prepared by the reaction of isothiocyanate with amine. 

---