Precise hybrid synthesis of glycoprotein through amino acid sequence-specific introduction of oligosaccharide followed by enzymatic transglycosylation reaction

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It is difficult to obtain homogeneous glycoproteins, although it is increasing our knowledge concerning physiological functions of glycoproteins. Nowadays, it is very easy to obtain bare proteins that fold appropriately by using prokaryote cells like Escherichia coli, and it is possible to obtain desired glycoproteins by conjugating with oligosaccharide and proteins precisely. Recently, it was reported that the Amadori rearrangement occurred between oligosaccharides and proteins in a sequence specific manner. Based on this report, I have investigated the effect of additives on the Amadori rearrangement reaction and acceleration of its reaction rate. The most striking result was that the effects of borate ion were depended upon chemical structure of sugars. For example, very large reaction rate using D-fructose was observed in phosphate buffer, although almost no reaction was observed in borate buffer. Investigation of sequence specificity of the Amadori rearrangement is under way.