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Sialyl Tn Unit with TFA-Labile Protection Realizes Efficient Synthesis of Sialyl Glycoprotein

Sialyl Tn Unit with TFA-Labile Protection Realizes Efficient Synthesis of Sialyl Glycoprotein

Chemistry 24(11): 2593-2597

Amino acids bearing 4-methylbenzyl (MBn) and 4-methoxybenzyl (MPM)-protected sialic acid were synthesized and used for the 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase synthesis of a glycopeptide. The α-sialyl linkage of the MBn-protected unit was partially cleaved under the final deprotection by trifluoroacetic acid (TFA). In addition, the removal of several MBn groups were incomplete. On the other hand, the MPM-protected unit gave the desired glycopeptide without decomposition of the α-sialyl linkage. Using this unit, peptide thioesters of the tandem repeat unit of MUC1 mucin were synthesized by the N-alkylcysteine (NAC) method and used for the one-pot ligation by the thioester method. As a result, the three tandem repeats of MUC1 carrying sialyl Tn antigens were successfully synthesized.

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Accession: 065512415

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PMID: 29314327

DOI: 10.1002/chem.201706127

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