60280-58-2
Chemical Structure
Gal beta(1-3)GalNAc-alpha-Thr
Synonym(s): TF-Thr
- CAS No.: 60280-58-2
- Formula:C18H32N2O13
- Molecular Weight:484.46
IUPAC Name: O-((2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)-L-threonine
InChIKey: VWNOCGQJSBAAFO-RBMHVKAPSA-N
SMILES: N(C(C)=O)[C@@H]1[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]([C@@H](C(O)=O)N)C
Biological Activity: Gal beta (1-3) GalNAc-alpha-Thr (TF-Thr) is a tumor-associated Thomsen-Friedenreich (TF) O-glycan and a ligand of galectin-3, with a human Kd value of 288 µM. Gal beta (1-3) GalNAc-alpha-Thr binds to the CRD of galectin-3 through the TF disaccharide and β-D-Galp/α-D-GalpNAc contacts, perturbing amide resonances and dynamics. Gal beta (1-3) GalNAc-alpha-Thr weakly binds to MGL-CRD through the terminal Gal rather than GalNAc. Gal beta (1-3) GalNAc-alpha-Thr competes with cell surface TF/MUC1 for Peanut Agglutinin (HY-P3443) binding, blocking Peanut Agglutinin-mediated adhesion of cancer cells to endothelium. Gal beta (1-3) GalNAc-alpha-Thr can be used in cancer-related research[1][2][3][4].
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Gal beta(1-3)GalNAc-alpha-Thr | Gal beta (1-3) GalNAc-alpha-Thr (TF-Thr) is a tumor-associated Thomsen-Friedenreich (TF) O-glycan and a ligand of galectin-3, with a human Kd value of 288 µM. Gal beta (1-3) GalNAc-alpha-Thr binds to the CRD of galectin-3 through the TF disaccharide and β-D-Galp/α-D-GalpNAc contacts, perturbing amide resonances and dynamics. Gal beta (1-3) GalNAc-alpha-Thr weakly binds to MGL-CRD through the terminal Gal rather than GalNAc. Gal beta (1-3) GalNAc-alpha-Thr competes with cell surface TF/MUC1 for Peanut Agglutinin (HY-P3443) binding, blocking Peanut Agglutinin-mediated adhesion of cancer cells to endothelium. Gal beta (1-3) GalNAc-alpha-Thr can be used in cancer-related research. | |||||||||||||||||||||
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References
- [1]. Yongye AB, et al. Molecular recognition of the Thomsen-Friedenreich antigen-threonine conjugate by adhesion/growth regulatory galectin-3: nuclear magnetic resonance studies and molecular dynamics simulations. Biochemistry. 2012 Sep 18;51(37):7278-89.
- [2]. Rodriguez MC, et al. Thermodynamic Switch in Binding of Adhesion/Growth Regulatory Human Galectin-3 to Tumor-Associated TF Antigen (CD176) and MUC1 Glycopeptides. Biochemistry. 2015 Jul 28;54(29):4462-74.
- [3]. Grosso AS, et al. Presentation Is Essential for Glycan-Lectin Recognition at the Molecular and Cellular Levels: The Interaction of Tumor-Associated ‑Glycans with the Macrophage Galactose-Type Lectin. JACS Au. 2026 Jan 26;6(1):82-94.
- [4]. Zhao Q, et al. Peanut agglutinin appearance in the blood circulation after peanut ingestion mimics the action of endogenous galectin-3 to promote metastasis by interaction with cancer-associated MUC1. Carcinogenesis. 2014 Dec;35(12):2815-21.
