
TAMRA Picolyl Azide
| Catalog Number | F07-0011 |
| Category | TAMRA Dyes |
| Molecular Formula | C42H48N8O9 |
| Molecular Weight | 808.9 |
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Product Introduction
TAMRA Picolyl Azide is an advanced fluorescent probe that incorporates a copper-chelating motif to raise the effective concentration of Cu(I) at the reaction site. The rate of CuAAC reaction depends on concentrations of all reagents, including copper, thus the raise of the effective copper concentration at the reaction site dramatically increase the rate of CuAAC reaction without the need to increase concentration of azide reagent and copper. This probe is compatible with various excitation sources including mercury arc, tungsten and xenon arc lamps, the 544 nm line of the Helium-Neon laser and the 532 nm green laser line.
In addition, the use of TAMRA Picolyl Azide instead of conventional TAMRA Azide allows for at least a tenfold reduction in the concentration of the copper catalyst without sacrificing the efficiency of labeling.
In summary, the introduction of a picolyl moiety into an azide probe leads to a substantial increase in the sensitivity of alkyne detection. This will be of special value for the detection of low abundance targets or where significant increase in signal intensity is desired.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Synonyms | 5-TAMRA Picolyl Azide |
| IUPAC Name | 5-[2-[2-[2-[2-[3-[[6-(azidomethyl)pyridin-3-yl]amino]-3-oxopropoxy]ethoxy]ethoxy]ethoxy]ethylcarbamoyl]-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=C(C=C4)C(=O)NCCOCCOCCOCCOCCC(=O)NC5=CN=C(C=C5)CN=[N+]=[N-])C(=O)[O-] |
| InChI | InChI=1S/C42H48N8O9/c1-49(2)31-8-11-34-37(24-31)59-38-25-32(50(3)4)9-12-35(38)40(34)33-10-5-28(23-36(33)42(53)54)41(52)44-14-16-56-18-20-58-22-21-57-19-17-55-15-13-39(51)47-30-7-6-29(45-26-30)27-46-48-43/h5-12,23-26H,13-22,27H2,1-4H3,(H2-,44,47,51,52,53,54) |
| InChIKey | XWKGVUAUNNBNEO-UHFFFAOYSA-N |
| Solubility | DMSO, DMF, MeOH |
Product Specification
| Excitation | 553 |
| Emission | 575 |
| Storage | -20 °C |
Application
TAMRA Picolyl Azide is a TAMRA-based fluorescent azide designed for copper-free and/or copper-catalyzed azide-alkyne cycloaddition workflows in chemical biology. The picolyl azide functionality enables efficient incorporation of the dye into biomolecules, linkers, and surfaces, while the TAMRA fluorophore provides strong visible fluorescence for imaging and assay development.
1. Biomolecule Click Labeling
TAMRA Picolyl Azide is used by chemical biology and glycobiology groups to install a TAMRA fluorophore onto biomolecules carrying complementary alkyne handles, including peptides, proteins, and other engineered constructs. Researchers commonly use the resulting triazole-linked conjugates for fluorescence microscopy, fluorescence imaging of labeled samples, and quantitative fluorescence readouts in labeling optimization studies. The azide handle supports straightforward downstream probe construction for tracking biomolecule localization, monitoring conjugation efficiency, and generating fluorescent standards for assay development.
2. Surface And Material Functionalization
TAMRA Picolyl Azide is applied in biomaterials and surface chemistry workflows where fluorescent tagging of functionalized materials is required. By clicking the azide onto alkyne-functionalized polymers, hydrogels, or solid supports, teams create fluorescently traceable surfaces for studying material-biomolecule interactions, coating uniformity, and transport or adsorption behavior. This approach is frequently used in materials research labs and industrial R&D settings to produce labeled scaffolds and reference materials for imaging-based characterization and process development.
3. Fluorescent Probe Construction
TAMRA Picolyl Azide serves as a dye-building block for fluorescent probe development, particularly when a TAMRA reporter needs to be appended to a larger recognition or targeting scaffold via click chemistry. Probe developers use the azide to generate modular conjugates that can be incorporated into affinity reagents, imaging reagents, or multi-component labeling schemes where the TAMRA signal provides a convenient optical readout. In fluorescence-based screening and assay development, the reagent supports rapid assembly of probe variants for evaluating labeling performance and signal behavior in instrument-compatible formats.
4. Oligonucleotide And Linker Conjugates
TAMRA Picolyl Azide is also used to prepare fluorescent oligonucleotide conjugates and defined dye-linker constructs for nucleic acid workflows. Laboratories incorporate the TAMRA reporter into alkyne-bearing oligonucleotide scaffolds or synthetic linkers to enable visualization of labeled strands, tracking of hybridization-related steps, and fluorescence-based monitoring of conjugate handling. This application is common in nucleic acid analysis method development where a stable, click-derived fluorescent tag is needed for consistent optical reporting across experimental batches.
Computed Properties
| XLogP3 | 3 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 13 |
| Rotatable Bond Count | 21 |
| Exact Mass | 808.35442514 g/mol |
| Monoisotopic Mass | 808.35442514 g/mol |
| Topological Polar Surface Area | 178Ų |
| Heavy Atom Count | 59 |
| Formal Charge | 0 |
| Complexity | 1560 |
| 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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