Fmoc-L-Thr(β-D-GlcNAc(Ac)3)-OH is a protected glycosylated threonine used in synthesis of O-linked glycopeptides. The triply acetylated GlcNAc enhances solubility and protects hydroxyl functions during coupling. Researchers use it to construct glycopeptide libraries and examine carbohydrate-peptide interactions. Its orthogonal protection scheme supports complex synthetic routes.
CAT No: HB00090
CAS No:160168-40-1
Synonyms/Alias:160168-40-1;Fmoc-L-Thr(beta-D-GlcNAc(Ac)3)-OH;(2S,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)butanoic acid;Fmoc-L-Thr(|A-D-GlcNAc(Ac)3)-OH;(2S,3R)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid;MFCD08274532;Fmoc-Thr(GlcNAc(Ac)--D)-OH;OXLCJWGAUPPZQJ-WPYJLJGXSA-N;EX-A3854;Fmoc-Thr(GlcNAc(Ac)3-?-D)-OH;AKOS037648919;Fmoc-L-Thr(ss-D-GlcNAc(Ac)3)-OH;BS-16025;MF111403;CS-0186052;FMOC-L-THR(| cent-D-GLCNAC(AC)3)-OH;D80724;2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-?-D-glucopyranosyl-Fmoc threonine;(2S,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)butanoicacid;(2S,3R)-3-{[(2R,3R,4R,5S,6R)-4,5-BIS(ACETYLOXY)-6-[(ACETYLOXY)METHYL]-3-ACETAMIDOOXAN-2-YL]OXY}-2-{[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO}BUTANOIC ACID;N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranosyl)-L-threonine (Fmoc-L-Thr(beta-D-GlcNAc(Ac)3)-OH);
Fmoc-L-Thr(β-D-GlcNAc(Ac)3)-OH is a specialized glycosylated amino acid derivative designed for advanced peptide synthesis applications. As a protected threonine residue bearing a β-D-N-acetylglucosamine moiety with acetylated hydroxyl groups, it enables precise incorporation of O-linked glycan structures into synthetic peptides. This compound is particularly relevant to glycopeptide research, where control over site-specific glycosylation is essential for probing protein function, molecular recognition, and biomolecular interactions. Its Fmoc-protected α-amino group and side-chain acetylation provide chemical stability and compatibility with standard solid-phase peptide synthesis (SPPS) protocols, making it a valuable building block for constructing complex glycoprotein mimetics and studying post-translational modifications.
Glycopeptide Synthesis: The primary application of this glycosylated amino acid is in the synthesis of O-linked glycopeptides via Fmoc-based SPPS. Its structure allows researchers to introduce defined GlcNAc-modified threonine residues into peptide chains with high fidelity, facilitating the generation of homogeneous glycopeptide libraries. These synthetic glycopeptides are instrumental in elucidating the roles of glycosylation in protein folding, stability, and function, as well as in mapping glycosylation sites relevant to various biological processes.
Glycosylation Mechanism Studies: By incorporating Fmoc-L-Thr(β-D-GlcNAc(Ac)3)-OH into model peptides, scientists can investigate the biochemical consequences of O-GlcNAc modification on protein substrates. This application supports detailed studies of enzymatic glycosylation pathways, substrate specificity of glycosyltransferases, and the effects of glycan structure on recognition by lectins or antibodies. Such investigations are crucial for understanding the molecular basis of glycan-mediated signaling and regulation.
Biomolecular Interaction Analysis: Synthetic peptides containing this glycosylated threonine residue serve as powerful tools for probing interactions between glycoproteins and carbohydrate-binding proteins. Through surface plasmon resonance, isothermal titration calorimetry, or other biophysical techniques, researchers can quantitatively assess binding affinities and specificities, advancing knowledge of cell-cell communication, immune recognition, and pathogen-host interactions that are mediated by O-linked GlcNAc motifs.
Analytical Method Development: The well-defined structure of Fmoc-L-Thr(β-D-GlcNAc(Ac)3)-OH makes it an ideal standard or reference compound for developing and validating analytical methods targeting glycopeptides. It can be used to optimize conditions for high-performance liquid chromatography (HPLC), mass spectrometry, or capillary electrophoresis, enabling sensitive detection and accurate characterization of glycosylated peptides in complex mixtures.
Glycoprotein Engineering: In the context of protein engineering and biomaterials research, this protected glycosylated threonine residue supports the site-specific introduction of glycan motifs into recombinant proteins or peptide-based scaffolds. Such applications are pivotal for designing glycomimetic therapeutics, vaccine candidates, or functional materials that harness the unique properties conferred by O-linked GlcNAc modifications. By enabling precise control over glycan placement, it empowers researchers to dissect structure-function relationships and tailor biomolecules for specific research or industrial objectives.
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