Synthesis of complex-type glycan containing LacdiNAc structure and its application to the glycoprotein synthesis

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Glycodelin A (GdA), a glycoprotein of 162 amino acid residues, has unusual carbohydrate structures composed of GalNAc-GlcNAc (LacdiNAc), and is engaged in important biological processes, such as fertilization. To promote the functional analysis of GdA as well as LacdiNAc-containing glycan, an access to GdA having homogeneous glycan is required. In this research, the efficient synthetic route of GdA having homogeneous glycan was examined. The synthesis of LacdiNAc-containing carbohydrate was realized by our benzyl-protection strategy. The polypeptide composed of the entire GdA sequence carrying GlcNAcs was then assembled by the native chemical ligation method combined with our N-alklycysteine-assisted thioesterification method. After folding, GdA having GlcNAcs was reacted with LacdiNAc sugar by glycosynthase to derivatize into GdA having LacdiNAc sugar.