Fmoc-L-ser(((Ac)4-β-D-Gal-O-(Ac)3-α-D-GalNAc)-OH is an Fmoc-protected L-serine derivative bearing a glycosylated side chain in which β-D-galactose and α-D-GalNAc are connected through an O-glycosidic linkage and fully acetylated with multiple acetate groups. The serine core contains an Fmoc carbamate on the amino functionality and a free carboxylic acid, while the side-chain hydroxyl is O-substituted by the peracetylated disaccharide, providing an array of esterified ring oxygen atoms that modulate polarity and protect the sugar hydroxyls during synthesis. In peptide and glycoconjugate assembly workflows, this protected amino acid is used as a building block for introducing a protected glycosylated serine residue into larger peptide or glycopeptide structures, supporting controlled stepwise coupling and subsequent deprotection strategies to reveal the corresponding carbohydrate functionality.
CAT No: HB00010
Fmoc-L-ser(((Ac)4-β-D-Gal-O-(Ac)3-α-D-GalNAc)-OH is an Fmoc-protected serine glycosylated with a disaccharide motif containing β-D-galactose linked to α-D-GalNAc, with multiple acetyl protecting groups on the sugar hydroxyls. This protected, carbohydrate-functionalized amino acid is designed for assembling glycopeptide structures in peptide synthesis workflows where the glycan must be carried through chain assembly under orthogonal protection. The combination of an Fmoc amino terminus with acetyl-protected sugar hydroxyls supports routine peptide coupling while keeping the carbohydrate functionality protected until downstream deprotection and glycan unveiling.
1. Glycopeptide Building Block
Fmoc-L-ser(((Ac)4-β-D-Gal-O-(Ac)3-α-D-GalNAc)-OH is used as a site-specific glycosylated residue for constructing glycopeptides that mimic mucin-like O-glycosylation patterns, where serine is the glycosylation anchor. Researchers in glyco-chemistry and chemical biology incorporate this building block into peptide sequences to generate defined glycan-peptide conjugates for binding studies, epitope mapping, and structure-activity relationship work. The acetyl-protected sugar hydroxyls help maintain the carbohydrate integrity during peptide chain assembly, while the Fmoc group enables standard stepwise synthesis on peptide platforms.
2. Solid-Phase Glycopeptide Synthesis
Fmoc-L-ser(((Ac)4-β-D-Gal-O-(Ac)3-α-D-GalNAc)-OH is commonly selected for solid-phase peptide synthesis workflows requiring a glycosylated amino acid compatible with iterative coupling and Fmoc deprotection cycles. Glycopeptide developers use this reagent to prepare homogeneous glycan-bearing peptides with the glycosylated serine positioned precisely within the sequence, supporting reproducible downstream conjugation, purification, and analytical characterization. The protected carbohydrate framework reduces side reactions associated with free sugar hydroxyls under peptide synthesis conditions, improving the practicality of assembling longer glycopeptide constructs.
3. Glycan Deprotection and Remodeling
Fmoc-L-ser(((Ac)4-β-D-Gal-O-(Ac)3-α-D-GalNAc)-OH is used as a protected glycan precursor that can be carried through peptide synthesis and later converted to a deprotected carbohydrate for functional studies. After peptide assembly, chemists typically remove acetyl groups to expose the native-like sugar hydroxyl pattern needed for enzymatic recognition, receptor/lectin binding experiments, or further glycan remodeling steps. This workflow is particularly useful when the final glycopeptide must present a specific O-glycan topology while the synthesis stage demands stable, protected functionality.
4. Analytical Standard for Glycopeptides
Fmoc-L-ser(((Ac)4-β-D-Gal-O-(Ac)3-α-D-GalNAc)-OH supports analytical method development and reference material preparation for characterizing glycopeptides containing the same Gal-GalNAc motif on serine. Analytical chemists and glycomics method developers use this defined building block to generate calibration or verification samples for LC-MS/MS characterization, fragmentation behavior assessment, and retention-time benchmarking of glycopeptides with comparable glycan composition. The well-defined protected structure helps ensure that observed mass and fragmentation features correspond to a reproducible glycan-bearing serine residue, improving confidence in analytical workflows.
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