
DBCO-PEG3-amine
| Catalog Number | R01-0289 |
| Category | Cycloalkyne Dyes (DBCO) |
| Molecular Formula | C27H33N3O5 |
| Molecular Weight | 479.57 |
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Product Introduction
DBCO-PEG3-amine is a reagent that features a dibenzocyclooctyne (DBCO) moiety, which participates in strain-promoted azide-alkyne cycloaddition (SPAAC) reactions, enabling copper-free click chemistry applications. The compound incorporates a polyethylene glycol (PEG) spacer with three ethylene glycol units, enhancing solubility and reducing steric hindrance during bioconjugation processes. Its terminal amine group allows for further functionalization or conjugation to biomolecules, supporting applications in surface modification, polymer functionalization, and linker design.
Chemical Information
Product Specification
Application
Computed Properties
Patents
Chemical Information
| Synonyms | DBCO-C4-PEG3-amine |
| Purity | >90% |
| IUPAC Name | N-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethyl]-4-(2-azatricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl)-4-oxobutanamide |
| SMILES | C1C2=CC=CC=C2C#CC3=CC=CC=C3N1C(=O)CCC(=O)NCCOCCOCCOCCN |
| InChI | InChI=1S/C27H33N3O5/c28-13-15-33-17-19-35-20-18-34-16-14-29-26(31)11-12-27(32)30-21-24-7-2-1-5-22(24)9-10-23-6-3-4-8-25(23)30/h1-8H,11-21,28H2,(H,29,31) |
| InChIKey | ZDMKBOWJBWTBIN-UHFFFAOYSA-N |
| Solubility | DCM, THF, acetonitrile, DMF and DMSO |
| Appearance | Light yellow oil |
Product Specification
| Storage | -20 °C |
Application
DBCO-PEG3-amine is a cyclooctyne-based click chemistry reagent designed for strain-promoted azide–alkyne cycloaddition (SPAAC) with azide-bearing partners under catalyst-free conditions. The molecule combines a DBCO (dibenzocyclooctyne) reactive handle with a short, flexible PEG3 spacer and a terminal primary amine, which is commonly used to introduce orthogonal functionality after click conjugation. This dual functionality supports robust labeling, surface functionalization, and downstream coupling workflows in chemical biology, biomaterials, and molecular imaging tool development.
1. PEGylated Surface Functionalization
DBCO-PEG3-amine is widely used to functionalize azide-presenting surfaces and scaffolds, where the PEG spacer helps control conjugation density and improves accessibility of the terminal amine for subsequent chemistry. Researchers incorporate this reagent into coating and patterning workflows to generate amine-bearing interfaces that can be further modified with activated carboxylates, NHS-esters, or other electrophiles. The DBCO handle enables rapid SPAAC attachment to azide-functional substrates, making it a practical choice for preparing reusable materials and standardized conjugation platforms for analytical and materials research.
2. Bioconjugation Linker Building Blocks
DBCO-PEG3-amine serves as a convenient linker intermediate for constructing multi-functional bioconjugates, particularly when a click-installed PEG spacer and a primary amine are needed for orthogonal downstream attachment. In chemical biology workflows, the terminal amine supports coupling to dyes, affinity tags, or other reactive moieties after the initial SPAAC step, enabling modular probe assembly without relying on metal catalysts. This reagent is commonly selected for building probe libraries and conjugation series where consistent spacing and reactive handle availability are important for reproducible labeling and characterization.
3. Molecular Imaging Probe Preparation
DBCO-PEG3-amine is used in the preparation of azide-functional imaging reagents and fluorescent or luminescent probe constructs, where the PEG3 spacer can reduce steric hindrance and help maintain probe responsiveness to labeling chemistry. After SPAAC installation onto azide-bearing targeting or reporter components, the terminal amine provides a convenient handle for attaching imaging dyes, chelators, or reporter groups through standard amide-forming or amine-reactive chemistries. Teams developing molecular imaging toolkits often favor this reagent because it supports a streamlined, modular build process for generating chemically defined probe conjugates.
4. Diagnostic Reagent and Assay Materials
DBCO-PEG3-amine is applied to the fabrication of assay reagents and diagnostic research materials that require controlled immobilization and secondary functionalization. Azide-containing capture elements, polymer supports, or bead-based platforms can be clicked with DBCO-PEG3-amine to install a PEG spacer and expose a terminal amine, which then enables attachment of additional binding ligands, reporters, or surface chemistries. This approach is frequently used in reagent development settings to create customizable assay surfaces and multiplexable conjugate formats with consistent linker architecture.
Computed Properties
| XLogP3 | 0.7 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 14 |
| Exact Mass | 479.24202116 g/mol |
| Monoisotopic Mass | 479.24202116 g/mol |
| Topological Polar Surface Area | 103Ų |
| Heavy Atom Count | 35 |
| Formal Charge | 0 |
| Complexity | 718 |
| 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 |
|---|---|---|
| US-2021386866-A1 | Antibody-drug conjugates containing an anti-mesothelin antibody and uses thereof | 2020-06-05 |
| US-2021308276-A1 | Heteroaryl sulfone-based conjugation handles, methods for their preparation, and their use in synthesizing antibody drug conjugates | 2016-08-03 |
| US-2020069717-A1 | Nucleotide derivatives and methods of use thereof | 2016-05-23 |
| WO-2017205336-A1 | Nucleotide derivatives and methods of use thereof | 2016-05-23 |
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