CAS 120173-57-1: A Building Block for Glycopeptide Synthesis

Fmoc-Ser[α-D-GalNAc(Ac)3]-OH is a defined glycosylated amino acid building block for glycobiology and glycopeptide chemistry.

Chemical information

Chemical name: N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-serine. Common name: Fmoc-Ser[α-D-GalNAc(Ac)3]-OH. Molecular formula: C₃₂H₃₆N₂O₁₃. Molecular weight: 656.63 g/mol. CAS number: 120173-57-1. Classification: Glycopeptides.

Structural features

The N-terminal Fmoc group is removable under basic conditions and is compatible with standard Fmoc solid-phase peptide synthesis (SPPS). The serine side-chain oxygen links to an α-D-N-acetylgalactosamine derivative, reproducing a motif found in mucin-type O-glycosylation. The sugar bears an N-acetyl group at C2 and O-acetyl groups at C3, C4, and C6. The O-acetyl groups protect the sugar hydroxyls during peptide assembly and can be removed for subsequent work.

Applications

Glycopeptides and glycoprotein mimics

This building block can introduce GalNAc at a defined site in an Fmoc-SPPS workflow. It supports the preparation of structurally defined glycopeptides and glycoprotein fragments for studying how O-glycosylation affects protein structure, stability, and function.

Drug and vaccine research

Glycopeptides prepared with this reagent can serve as research tools for tumor-associated carbohydrate antigens, including the Tn antigen (GalNAcα1-O-Ser/Thr), in early research on cancer vaccines and targeted agents.

Carbohydrate–protein interactions

The reagent can help produce uniform glycosylated probes for studying recognition by lectins, antibodies, and receptors, with applications in basic research and diagnostic development.

Practical synthesis

A preassembled glycosylated amino acid reduces the need to prepare the building block from scratch. Its compatibility with automated peptide synthesis can improve efficiency and reproducibility.

Conclusion

This reagent connects carbohydrate chemistry with peptide synthesis and supports site-specific glycosylation studies.

Prepared by KASONS. For research use only.