
3-Azidopropanoic acid-PFP ester | CAS 1240801-10-8
| Catalog Number | R14-0301 |
| Category | Azides |
| Molecular Formula | C9H4F5N3O2 |
| Molecular Weight | 281.1 |
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Product Introduction
3-Azidopropanoic acid-PFP ester is an azidopropanoic acid linker that contains an activated PFP ester. The azide group can undergo copper-catalyzed Click Chemistry reactions with alkynes, DBCO and BCN to form triazole linkages. The activated PFP ester can react with amine groups to form stable amide bonds. They are also less susceptible toward undergoing hydrolysis.
Chemical Information
Product Specification
Application
Computed Properties
Patents
Chemical Information
| Synonyms | 3-Azidopropionic acid pentafluorophenyl ester |
| Purity | 98% |
| IUPAC Name | (2,3,4,5,6-pentafluorophenyl) 3-azidopropanoate |
| SMILES | C(CN=[N+]=[N-])C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F |
| InChI | InChI=1S/C9H4F5N3O2/c10-4-5(11)7(13)9(8(14)6(4)12)19-3(18)1-2-16-17-15/h1-2H2 |
| InChIKey | FRSRZMNVGWVIJB-UHFFFAOYSA-N |
Product Specification
| Storage | -20 °C |
Application
3-Azidopropanoic acid-PFP ester is an azide-functionalized carboxylic acid derivative equipped with a pentafluorophenyl (PFP) ester, making it a versatile click-chemistry handle for biomolecular labeling workflows. As a PFP ester, it is commonly used to form stable amide linkages with primary amines under standard bioconjugation conditions, while the pendant azide provides a bioorthogonal “click” group for subsequent strain-promoted or copper-catalyzed azide-alkyne cycloaddition. This combination is frequently leveraged in molecular imaging, diagnostic reagent development, and materials functionalization where a controllable conjugation site and a downstream click handle are both required.
1. Amine-Targeted Bioconjugation
3-Azidopropanoic acid-PFP ester is widely used to introduce an azide-bearing spacer onto proteins, peptides, and other amine-containing biomolecules via PFP-ester coupling. Researchers select this reagent when they need a robust conjugation step that leaves an azide group accessible for later click attachment of fluorophores, affinity tags, or reporter scaffolds. The resulting azide-functional conjugates are commonly used as intermediate building blocks for modular probe assembly, enabling consistent labeling strategies across different targets such as antibodies, enzyme conjugates, and affinity ligands.
2. Modular Probe Assembly
3-Azidopropanoic acid-PFP ester supports modular construction of multicomponent chemical biology tools by installing an azide handle that can be clicked to complementary partners. In practice, this enables sequential workflows where an azide-bearing biomolecule is first prepared, then reacted with alkyne-functional imaging dyes, biotin analogs, polymeric reporters, or other detection moieties to generate final probes with defined composition. The reagent’s azide functionality is particularly valuable for workflows that require orthogonal coupling steps, allowing the click stage to be tuned to the desired readout chemistry without re-optimizing the initial bioconjugation.
3. Molecular Imaging Reagent Development
3-Azidopropanoic acid-PFP ester is used in the development of imaging reagents where azide-tagged biomolecular components serve as platforms for attaching imaging reporters. Typical use cases include preparing azide-functional antibodies or binding proteins that are subsequently clicked to imaging-active ligands, fluorescent reporters, or other signal-generating constructs used in microscopy and molecular imaging assay development. This two-step design helps separate the amine-targeted installation of the azide spacer from the final attachment of the imaging reporter, improving flexibility when screening reporter chemistries and labeling densities.
4. Surface and Materials Functionalization
3-Azidopropanoic acid-PFP ester is also applied to functionalize surfaces and biomaterials that present primary amines, such as amine-terminated polymers, hydrogel matrices, and modified solid supports. By coupling through the PFP ester functionality, the reagent introduces azide groups into material architectures, enabling subsequent click-based immobilization of ligands, crosslinkers, or detection probes. This approach is frequently adopted in assay development and materials chemistry to create stable, modular interfaces where the azide content can be used to control downstream attachment of fluorescent or affinity components.
Computed Properties
| XLogP3 | 3 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 5 |
| Exact Mass | 281.02236719 g/mol |
| Monoisotopic Mass | 281.02236719 g/mol |
| Topological Polar Surface Area | 40.7Ų |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Complexity | 363 |
| 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-2022130046-A1 | N-1 branched imidazoquinolines, conjugates thereof, and methods | 2020-12-16 |
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