
FAM tetrazine, 5-isomer
| Catalog Number | R08-0011 |
| Category | Fluorescein FAM |
| Molecular Formula | C31H21N5O6 |
| Molecular Weight | 559.53 |
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Product Introduction
Tetrazine (methyltetrazine) derivative of fluorescein, pure 5-isomer. Tetrazines are reactive heterodiene components for [4+2] inverse electron demand Diels-Alder reaction (ied-DA) with strained cycloalkenes (trans-cyclooctenes, cyclopropenes). This reaction is also called TCO (tetrazine-cyclooctene) ligation. The reaction is among the fastest bioconjugation reactions.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Synonyms | 5-isomer FAM tetrazine |
| Purity | NMR 1H, HPLC-MS (95%) |
| IUPAC Name | 3',6'-dihydroxy-N-[[4-(6-methyl-1,2,4,5-tetrazin-3-yl)phenyl]methyl]-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxamide |
| SMILES | CC1=NN=C(N=N1)C2=CC=C(C=C2)CNC(=O)C3=CC4=C(C=C3)C5(C6=C(C=C(C=C6)O)OC7=C5C=CC(=C7)O)OC4=O |
| InChI | InChI=1S/C31H21N5O6/c1-16-33-35-28(36-34-16)18-4-2-17(3-5-18)15-32-29(39)19-6-9-23-22(12-19)30(40)42-31(23)24-10-7-20(37)13-26(24)41-27-14-21(38)8-11-25(27)31/h2-14,37-38H,15H2,1H3,(H,32,39) |
| InChIKey | VWBVWYWGTPSCBT-UHFFFAOYSA-N |
| Solubility | good in DMF, DMSO |
| Appearance | yellow solid |
Product Specification
| ε, L⋅mol-1⋅cm-1 | 80000 |
| Fluorescence Quantum Yield | 0.93 |
| Excitation | 490 |
| Emission | 513 |
| Storage | 24 months after receival at -20°C in the dark. Transportation: at room temperature for up to 3 weeks. Avoid prolonged exposure to light. Desiccate. |
Application
FAM tetrazine, 5-isomer is a tetrazine-functional fluorescent labeling reagent designed for inverse-electron-demand Diels-Alder click chemistry workflows. The tetrazine moiety enables fast covalent conjugation to strained alkene partners used in bioorthogonal labeling, while the FAM fluorophore provides fluorescence readout for tracking labeling efficiency and localization in complex biological samples. This combination supports reagent development and imaging experiments where covalent attachment and fluorescence visualization are both required.
1. Bioorthogonal Biomolecule Labeling
FAM tetrazine, 5-isomer is used by chemical biology and glycobiology groups to covalently label biomolecules in live-cell compatible labeling workflows that rely on strained-alkene click partners. Researchers incorporate it into labeling strategies for proteins, peptides, and other macromolecules to generate fluorescent conjugates for downstream microscopy and quantitative fluorescence readouts. Because the tetrazine handle provides a direct route to stable conjugates, the reagent is commonly selected when transient, noncovalent dye association would otherwise complicate interpretation of cellular or biochemical experiments.
2. Fluorescence Imaging Probe Construction
FAM tetrazine, 5-isomer supports the construction of fluorescent imaging reagents where the fluorophore is installed through tetrazine-mediated click conjugation to a targeting or scaffold component bearing a strained alkene. Molecular imaging and microscopy laboratories use the resulting fluorescent conjugates to visualize labeled biomolecular assemblies, track conjugate formation in situ, and map distribution in experimental systems such as labeled cell-surface targets or extracellular binding studies. The FAM emission is leveraged for standard fluorescence microscope channels and for assay development that benefits from straightforward excitation/emission compatibility with common FITC-style detection setups.
3. Click-Driven Surface Functionalization
FAM tetrazine, 5-isomer is applied in biomaterials and surface chemistry workflows to fluorescently tag or verify functionalization of materials engineered with strained-alkene groups. Researchers use it to create fluorescently labeled surfaces or coatings that report on the extent and uniformity of surface modification, supporting studies in materials characterization, surface binding experiments, and multicomponent assembly of functional interfaces. This use is particularly common in laboratories that need a covalent fluorescent marker to distinguish successful surface coupling from residual unreacted components after washing steps.
4. Flow Cytometry Labeling Verification
FAM tetrazine, 5-isomer is frequently used as a fluorescence reporter to confirm click labeling outcomes in cell-based workflows that require covalent attachment. Flow cytometry users employ the reagent to generate fluorescently labeled populations after conjugation to strained-alkene biomolecules or probes, enabling gating and quantification of labeling levels across experimental conditions. The tetrazine-driven covalent attachment helps reduce ambiguity from loosely associated fluorophores, supporting more reliable interpretation of labeling-dependent shifts in fluorescence intensity during assay optimization.
Computed Properties
| XLogP3 | 2.9 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 10 |
| Rotatable Bond Count | 4 |
| Exact Mass | 559.14918341 g/mol |
| Monoisotopic Mass | 559.14918341 g/mol |
| Topological Polar Surface Area | 157Ų |
| Heavy Atom Count | 42 |
| Formal Charge | 0 |
| Complexity | 974 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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