Method for producing glycopeptide having sialyl sugar chain, sialyl sugar chain-added amino acid derivative to be used in same, and glycopeptide

摘要

[Technical Problem];To provide a method for manufacturing that enables to obtain a targeted glycopeptide harboring a sialyl sugar chain in high yield without decomposing sialic acid at a non-reducing terminal of sugar chain when the glycopeptide is synthesized by a Boc solid phase synthesis method.;[Solution to Problem];The present invention is characterized in that the Boc-sialylglycosylated amino acid derivative used in Boc solid phase synthesis method is one where the carboxyl group of the sialic acid at the sugar chain non-reducing terminal is protected with a phenacyl group.

主权项

1. A method for manufacturing a glycopeptide having a sialyl sugar chain, characterized in that it comprises the following steps of:
(1) binding a resin having a hydroxyl group with an amino acid having the amino group nitrogen protected with a Boc group; wherein said binding step is a step of binding the hydroxyl group of said resin with the carboxyl group of said amino acid by an esterification reaction, (2) forming a free amino group by detaching said Boc group; (3) repeating at least once the following steps (i) and (ii) of:
(i) elongating the amino acid bound to the resin by further binding another amino acid having the amino group nitrogen protected with a Boc group, wherein said elongation step is a step of binding the carboxyl group of said another amino acid with said free amino group of the amino acid bound to said resin,
(ii) forming a free amino group by detaching said Boc group in (i); and (4) cleaving the resin with an acid; wherein said amino acid in step (1) and/or said another amino acid in at least one of (i) in step (3) is a glycosylated amino acid, said glycosylated amino acid has a sialic acid at at least one of the sugar chain non-reducing terminals, and the carboxyl group of said sialic acid is protected with a phenacyl group.