
Iodoacetamide-PEG3-azide
| Catalog Number | R14-0119 |
| Category | Azides |
| Molecular Formula | C10H19IN4O4 |
| Molecular Weight | 386.2 |
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Product Introduction
Iodoacetamide-PEG3-azide
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Synonyms | N-(2-{2-[2-(2-azidoethoxy)ethoxy]ethoxy}ethyl)-2-iodoacetamide |
| Purity | 98% |
| IUPAC Name | N-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl]-2-iodoacetamide |
| SMILES | C(COCCOCCOCCN=[N+]=[N-])NC(=O)CI |
| InChI | InChI=1S/C10H19IN4O4/c11-9-10(16)13-1-3-17-5-7-19-8-6-18-4-2-14-15-12/h1-9H2,(H,13,16) |
| InChIKey | MVKSZBZLUGCWFA-UHFFFAOYSA-N |
| Solubility | DMSO, DCM, DMF |
Product Specification
| Storage | -20 °C |
Application
Iodoacetamide-PEG3-azide is a PEG-linked azide click chemistry reagent that combines an iodoacetamide electrophile with an azide handle for subsequent bioorthogonal conjugation. As a bifunctional linker, it is commonly used to introduce an azide functionality onto nucleophilic biomolecule sites via thiol-reactivity, enabling downstream Cu-free or Cu-catalyzed azide-alkyne cycloaddition workflows. The PEG3 spacer supports aqueous solubility and helps reduce steric constraints, making the reagent well suited for generating azide-bearing probes for molecular imaging, diagnostics research, and modular biomaterial functionalization.
1. Thiol-Tagged Probe Labeling
Iodoacetamide-PEG3-azide is widely used to install azide groups onto thiol-containing biomolecules and labeling reagents, including cysteine- or thiol-terminated peptides, proteins, and antibody fragments used in assay development. The iodoacetamide moiety reacts with accessible sulfhydryl groups to create a stable thioether linkage, while the PEG3 spacer improves conjugate handling in aqueous buffers. Researchers then use the resulting azide-functionalized constructs as modular building blocks for attaching fluorophores, affinity tags, or imaging moieties through click chemistry, supporting streamlined probe generation for biochemical characterization and platform optimization.
2. Surface and Hydrogel Functionalization
Iodoacetamide-PEG3-azide is commonly applied in biomaterials workflows to introduce azide functionalities onto thiol-reactive surfaces and polymer networks prior to click-based patterning or coupling. In hydrogel and coating development, thiol-bearing substrates can be functionalized with the iodoacetamide chemistry to yield azide-presenting materials that are compatible with orthogonal conjugation strategies using alkyne-bearing crosslinkers or ligands. The PEG3 linker helps maintain surface accessibility of the azide handle, which is important for reproducible attachment densities and for enabling spatially controlled conjugation in materials research, including scaffold functionalization for extracellular matrix mimicry and multi-component material assembly.
3. Fluorophore and Imaging Conjugates
Iodoacetamide-PEG3-azide serves as a practical azide-introduction reagent for generating imaging-grade conjugates from thiol-containing targeting vectors and labeling intermediates. By converting sulfhydryl sites into azide-bearing handles, the reagent supports subsequent attachment of alkyne-functional dyes, affinity probes, or imaging reporters using click chemistry under conditions chosen for the compatibility of the assembled components. The PEG3 spacing is particularly useful when preparing fluorescent conjugates where steric accessibility influences labeling efficiency and signal stability in complex labeling workflows used for microscopy, bioimaging assay development, and molecular visualization tool creation.
4. Targeted Affinity Reagent Platforms
Iodoacetamide-PEG3-azide is frequently used to build azide-functional affinity reagents from thiol-containing binders, such as engineered binding proteins, antibody derivatives, or affinity peptides used in research reagent libraries. Conjugation workflows typically start by installing azide handles at defined thiol sites, after which alkyne-bearing components can be appended to generate multivalent binders, detection reagents, or capture probes. This modular approach aligns with how many diagnostic-research and molecular biology groups develop reagent panels, enabling rapid swapping of reporters and surface chemistries while maintaining a consistent conjugation strategy across different binder formats.
Computed Properties
| XLogP3 | 0.7 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 13 |
| Exact Mass | 386.04510 g/mol |
| Monoisotopic Mass | 386.04510 g/mol |
| Topological Polar Surface Area | 71.2Ų |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Complexity | 274 |
| 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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