Method for producing glycopeptide having sialyl sugar chain, sialyl sugar chain-added amino acid derivative to be used in same, and glycopeptide
AssigneeGlytech, Inc.
InventorsYasuhiro Kajihara, Masumi Murakami, Kazuyuki Ishii
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Abstract
[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.
Claims16
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.
A method for manufacturing a sialylglycoasparagine derivative in which the amino group of sialylglycoasparagine is protected with a Boc group and the carboxyl group of the sialic acid at the sugar chain non-reducing terminal is protected with a phenacyl group, comprising the steps of:
- introducing a phenacyl group into a sialylglycoasparagine derivative having the amino group of the asparagine protected with a lipophilic protecting group,
- detaching the lipophilic protecting group of the sialylglycoasparagine having a phenacyl group introduced, and
- introducing a Boc group into the sialylglycoasparagine having the lipophilic protecting group detached.
Dependencies are inferred from the claim text.