
TAMRA azide, 6-isomer | CAS 1192590-89-8
| Catalog Number | F07-0014 |
| Category | TAMRA Dyes |
| Molecular Formula | C28H28N6O4 |
| Molecular Weight | 512.6 |
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Product Introduction
TAMRA azide, 6-isomer is a linker of TAMRA which is a xanthene dye with orange emission. The addition of the azide groups allows for it to be reacted with alkynes, DBCO and BCN for copper-catalyzed Click Chemistry. This dye comes in a 5- and 6-isomer.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Synonyms | 5-TAMRA-Azide; 6-Carboxytetramethylrhodamine Azide |
| Purity | 95% |
| IUPAC Name | 4-(3-azidopropylcarbamoyl)-2-[3-(dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]benzoate |
| SMILES | CN(C)C1=CC2=C(C=C1)C(=C3C=CC(=[N+](C)C)C=C3O2)C4=C(C=CC(=C4)C(=O)NCCCN=[N+]=[N-])C(=O)[O-] |
| InChI | InChI=1S/C28H28N6O4/c1-33(2)18-7-10-21-24(15-18)38-25-16-19(34(3)4)8-11-22(25)26(21)23-14-17(6-9-20(23)28(36)37)27(35)30-12-5-13-31-32-29/h6-11,14-16H,5,12-13H2,1-4H3,(H-,30,35,36,37) |
| InChIKey | LCCOWUGYZJZMIT-UHFFFAOYSA-N |
| Solubility | DMF, DMSO, alcohols |
Product Specification
| Fluorescence Quantum Yield | 0.10 |
| Excitation | 541 |
| Emission | 567 |
| Storage | -20 °C |
Application
TAMRA azide, 6-isomer is a TAMRA-based fluorescent azide designed for copper-catalyzed azide-alkyne cycloaddition (CuAAC) labeling. As an azide handle, it enables efficient installation of a bright red/orange fluorophore onto biomolecules, polymers, and surfaces bearing alkyne groups, supporting downstream fluorescence imaging and quantitative assay development.
1. Biomolecule Labeling
TAMRA azide, 6-isomer is used by chemical biology and proteomics researchers to introduce a TAMRA fluorophore onto proteins, peptides, and other biomolecules that have been functionalized with terminal alkynes. In practice, this supports fluorescent labeling for tracking conjugate formation, assessing labeling stoichiometry, and visualizing biomolecular interactions in solution or on membranes. The azide functionality makes it straightforward to prepare fluorescent conjugates for microscopy workflows and fluorescence-based readouts where TAMRA emission is compatible with standard filter sets and plate reader channels.
2. Fluorescent Probe Construction
TAMRA azide, 6-isomer is commonly incorporated into fluorescent probe and reagent libraries where a TAMRA reporting group is required on a defined molecular scaffold. Researchers use it to build labeling reagents for oligonucleotides, affinity ligands, and modular probe constructs by clicking the TAMRA azide onto alkyne-bearing partners. This approach is frequently selected for generating calibration materials and imaging reagents that maintain a consistent fluorophore identity across probe variants, enabling comparative studies in fluorescence microscopy, gel-based fluorescence analysis, and assay development.
3. Surface And Polymer Functionalization
TAMRA azide, 6-isomer is applied in biomaterials and materials research to fluorescently tag surfaces, hydrogels, and polymer networks that contain alkyne functional groups. By installing TAMRA via click chemistry, teams can map coating uniformity, monitor surface modification steps, and generate fluorescently labeled materials for imaging of cell-material interfaces. This labeling strategy is also used to prepare fluorescent standards for process development and to support microscopy-based characterization of functionalized substrates.
4. Cell Imaging Labeling Studies
TAMRA azide, 6-isomer is used in cellular imaging studies where researchers label biomolecules or biomolecule-derived structures after alkyne functionalization. The resulting TAMRA conjugates enable fluorescence visualization of labeled targets under conventional fluorescence microscopy conditions, supporting experiments such as localization studies and workflow validation for multistep labeling schemes. In typical use, the click-installed TAMRA signal provides a robust fluorescent tag for tracking labeled components during sample preparation, washing, and imaging.
Computed Properties
| XLogP3 | 4.2 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 7 |
| Exact Mass | 512.21720340 g/mol |
| Monoisotopic Mass | 512.21720340 g/mol |
| Topological Polar Surface Area | 99.1Ų |
| Heavy Atom Count | 38 |
| Formal Charge | 0 |
| Complexity | 1060 |
| 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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