
TAMRA alkyne, 5-isomer | CAS 945928-17-6
| Catalog Number | R02-0036 |
| Category | Alkynes |
| Molecular Formula | C28H25N3O4 |
| Molecular Weight | 467.51 |
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Product Introduction
TAMRA alkyne for Click chemistry, pure 5-isomer. TAMRA (TMR, tetramethylrhodamine) is a xanthene dye. It forms a FRET pair with fluorescein. This alkyne is suitable for Copper-catalyzed Click chemistry (CuAAC).
Chemical Information
Product Specification
Application
Computed Properties
Patents
Chemical Information
| Synonyms | 5-TAMRA alkyne; 5-TAMRAalkyne; 5-Carboxytetramethylrhodamine-propargylamide; 2-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)-5-(prop-2-yn-1-ylcarbamoyl)benzoate; 2-(3,6-Bis(dimethylamino)xanthylium-9-yl)-5-(prop-2-yn-1-ylcarbamoyl)benzoate; 5-isomer TAMRA alkyne; 5-Carboxytetramethylrhodamine, propargylamide |
| Purity | NMR 1H, HPLC-MS (95%) |
| IUPAC Name | 2-[3-(dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]-5-(prop-2-ynylcarbamoyl)benzoate |
| SMILES | CN(C)C1=CC2=C(C=C1)C(=C3C=CC(=[N+](C)C)C=C3O2)C4=C(C=C(C=C4)C(=O)NCC#C)C(=O)[O-] |
| InChI | InChI=1S/C28H25N3O4/c1-6-13-29-27(32)17-7-10-20(23(14-17)28(33)34)26-21-11-8-18(30(2)3)15-24(21)35-25-16-19(31(4)5)9-12-22(25)26/h1,7-12,14-16H,13H2,2-5H3,(H-,29,32,33,34) |
| InChIKey | DYDBZMFMNBGTIP-UHFFFAOYSA-N |
| Solubility | good in DMF, DMSO, low in water |
| Appearance | violet solid |
Product Specification
| ε, L⋅mol-1⋅cm-1 | 84000 |
| Fluorescence Quantum Yield | 0.1 |
| Excitation | 541 |
| Emission | 567 |
| 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
TAMRA alkyne, 5-isomer is a TAMRA-based fluorescent labeling reagent bearing an alkyne handle for copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). This dye is commonly used to introduce bright, visible red fluorescence into biomolecules, polymers, and biomaterial surfaces via click chemistry, enabling downstream fluorescence microscopy, imaging, and assay development. The alkyne functionality supports efficient conjugation to azide-bearing targets, including fluorescent probe constructs and bioconjugates prepared for detection workflows.
1. Biomolecule Labeling
TAMRA alkyne, 5-isomer is used by chemical biology and glycobiology groups to fluorescently tag proteins, peptides, and other biomolecules that have been engineered or functionalized with azide groups. Researchers typically prepare azide-modified biomolecules (for example, via azide-functional linkers) and then click the TAMRA alkyne to generate TAMRA-labeled conjugates for fluorescence imaging and quantitative fluorescence readouts. This approach is particularly valuable when maintaining a defined labeling position is important for tracking biomolecule localization, trafficking, or binding behavior in assay formats compatible with red-emitting fluorophores.
2. Fluorescence Microscopy Imaging
TAMRA alkyne, 5-isomer supports fluorescence microscopy workflows where red fluorescence labeling is needed to visualize labeled biomolecules, cell-associated structures, or biomaterial interactions. In practice, investigators click the TAMRA dye onto azide-functional targeting reagents, surface coatings, or polymer networks to create fluorescent imaging tools for fixed-cell or in vitro microscopy experiments. The alkyne handle enables modular probe construction, allowing researchers to swap azide-bearing ligands (such as targeting peptides or affinity reagents) while keeping the TAMRA reporter constant for consistent imaging across experiments.
3. Flow Cytometry Labeling
TAMRA alkyne, 5-isomer is frequently incorporated into flow cytometry labeling strategies by first generating azide-containing biomolecule conjugates and then performing click labeling with the TAMRA alkyne reporter. This workflow is used to produce red-fluorescent conjugates for cell staining experiments, including labeling of cell-surface components, receptor-binding reagents, or assay reagents used to monitor biomolecular interactions by fluorescence intensity. Because the dye is introduced through a defined click step, it is often chosen when researchers want reproducible labeling of azide-functional constructs prior to instrument readout.
4. Biomaterial Surface Functionalization
TAMRA alkyne, 5-isomer is applied in biomaterials research to create fluorescently traceable surfaces and coatings through click chemistry on azide-functionalized materials. Scientists use TAMRA labeling to monitor material distribution, adsorption, and interface behavior in microscopy and fluorescence-based characterization studies. The alkyne reporter is also leveraged to generate fluorescent polymer conjugates and surface-tethered probes that can be used to track biomolecule attachment or visualize contact between engineered materials and biological components in vitro.
Computed Properties
| XLogP3 | 3.1 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Exact Mass | 467.18450629 g/mol |
| Monoisotopic Mass | 467.18450629 g/mol |
| Topological Polar Surface Area | 84.7Ų |
| Heavy Atom Count | 35 |
| Formal Charge | 0 |
| Complexity | 1000 |
| 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 |
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| WO-2020223368-A1 | Methods and systems for integrated on-chip single-molecule detection | 2019-04-29 |
| EP-3963091-A1 | Methods and systems for integrated on-chip single-molecule detection | 2019-04-29 |
| WO-2019195633-A1 | Methods of generating nanoarrays and microarrays | 2018-04-04 |
| CN-112236528-A | Methods of producing nanoarrays and microarrays | 2018-04-04 |
| EP-3775196-A1 | Methods of generating nanoarrays and microarrays | 2018-04-04 |
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