Tri-GalNAc(OAc)3 TFA is a fully acetylated trivalent N-acetylgalactosamine cluster used to study carbohydrate-protein recognition. The structure supports analyses of glycan density, lectin binding, and conformational behavior. Researchers use it to model multivalent carbohydrate interactions. Its TFA formulation ensures reliable solubility.
CAT No: R2176
CAS No:1159408-65-7
Synonyms/Alias:Tri-GalNAc(OAc)3 TFA;1159408-65-7;Tri-GalNAc(OAc)3 (TFA);EX-A7801G;HY-148118A;CS-0612259;G63035;
Tri-GalNAc(OAc)3 TFA, also known as Tris-N-acetylgalactosamine acetate trifluoroacetate, is a sophisticated carbohydrate compound widely recognized for its utility in biochemical research and molecular engineering. Characterized by its unique structure, which features three N-acetylgalactosamine units with acetylated hydroxyl groups and a trifluoroacetate counterion, this compound offers enhanced solubility and stability, making it particularly suitable for complex synthetic applications. Its chemical versatility allows for precise conjugation and labeling, facilitating the development of advanced glycoconjugates and targeted delivery systems. The compound's design enables researchers to exploit its high affinity for specific lectins and receptors, supporting the investigation of cellular recognition mechanisms and glycan-mediated biological processes.
Targeted Drug Delivery: Tri-GalNAc(OAc)3 TFA serves as a valuable tool in the development of targeted drug delivery systems, especially those aimed at hepatocyte-specific applications. The presence of multiple N-acetylgalactosamine residues enables the compound to bind selectively to asialoglycoprotein receptors (ASGPR) on liver cells. By conjugating therapeutic agents or nanoparticles with this carbohydrate moiety, researchers can achieve efficient and selective hepatic targeting, thereby enhancing the specificity and efficacy of their delivery vehicles. The acetylated form further improves the compound's stability and membrane permeability, optimizing its performance in the context of in vivo and in vitro delivery studies.
Glycoconjugate Synthesis: In the field of synthetic carbohydrate chemistry, Tris-GalNAc acetate is frequently employed as a building block for the construction of complex glycoconjugates. Its protected acetyl groups facilitate controlled glycosylation reactions, allowing for stepwise assembly of oligosaccharides and glycopeptides. This capability is particularly valuable for generating defined glycan structures that mimic natural ligands or epitopes, which are essential for studying glycan-protein interactions, developing glycan-based probes, and producing immunogens for research purposes. The compound's trifluoroacetate salt form also aids in purification and handling during multi-step synthetic processes.
Cellular Recognition and Imaging: The affinity of Tri-GalNAc derivatives for specific lectins and cell-surface receptors makes them indispensable in cellular recognition studies and imaging applications. Researchers utilize fluorescently labeled or biotinylated versions of this compound to probe the distribution and density of ASGPR on hepatocytes or to investigate glycan-mediated endocytosis pathways. These studies provide critical insights into cell signaling, receptor trafficking, and the dynamics of glycan-receptor interactions, contributing to a deeper understanding of cellular communication and molecular recognition events.
Bioconjugation and Surface Modification: The chemical reactivity and structural features of Tri-GalNAc(OAc)3 TFA make it an excellent candidate for bioconjugation and surface modification applications. By attaching this carbohydrate to proteins, peptides, or nanoparticles, scientists can engineer bioactive surfaces with tailored glycan presentations. Such modifications are instrumental in creating biomimetic materials, biosensors, and affinity matrices for glycoprotein purification or cell-capture technologies. The acetyl protection enhances the compound's compatibility with various chemistries, ensuring efficient coupling and functionalization under mild conditions.
Glycomics Research: As a specialized glycan building block, Tri-GalNAc(OAc)3 TFA plays a pivotal role in glycomics research, where the aim is to elucidate the structure, function, and biological significance of complex carbohydrates. By incorporating this compound into synthetic glycan arrays or using it as a standard in mass spectrometry and chromatographic analyses, researchers can systematically investigate glycan-protein interactions, map glycosylation patterns, and explore the diversity of glycan structures in biological samples. These efforts advance the field of glycobiology and enable the discovery of novel glycan biomarkers and therapeutic targets. In summary, the multifaceted applications of Tri-GalNAc(OAc)3 TFA underscore its significance as a versatile and indispensable tool for advancing carbohydrate research, molecular engineering, and the development of innovative biotechnological solutions.
1. High fat diet and GLP-1 drugs induce pancreatic injury in mice
2. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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