
Sulfo DBCO-PEG4-TFP ester
| Catalog Number | R01-0419 |
| Category | Cycloalkyne Dyes (DBCO) |
| Molecular Formula | C39H41F4N3O12S |
| Molecular Weight | 851.8 |
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Product Introduction
Sulfo DBCO-PEG4-TFP ester is a heterobifunctional crosslinker that features a dibenzocyclooctyne (DBCO) moiety and a tetrafluorophenyl (TFP) ester, linked by a polyethylene glycol (PEG) spacer. The DBCO group participates in strain-promoted azide-alkyne cycloaddition (SPAAC), enabling copper-free click chemistry reactions with azide-functionalized molecules, while the TFP ester reacts efficiently with primary amines under mild conditions, facilitating bioconjugation and surface modification. This reagent is commonly incorporated into labeling chemistry and polymer functionalization applications, where its PEG spacer enhances solubility and reduces steric hindrance, supporting versatile conjugation strategies in bioorthogonal chemistry contexts.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| IUPAC Name | 1-[[3-(2-azatricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl)-3-oxopropyl]amino]-1-oxo-3-[3-[2-[2-[2-[3-oxo-3-(2,3,5,6-tetrafluorophenoxy)propoxy]ethoxy]ethoxy]ethoxy]propanoylamino]propane-2-sulfonic acid |
| SMILES | C1C2=CC=CC=C2C#CC3=CC=CC=C3N1C(=O)CCNC(=O)C(CNC(=O)CCOCCOCCOCCOCCC(=O)OC4=C(C(=CC(=C4F)F)F)F)S(=O)(=O)O |
| InChI | InChI=1S/C39H41F4N3O12S/c40-29-23-30(41)37(43)38(36(29)42)58-35(49)13-16-55-18-20-57-22-21-56-19-17-54-15-12-33(47)45-24-32(59(51,52)53)39(50)44-14-11-34(48)46-25-28-7-2-1-5-26(28)9-10-27-6-3-4-8-31(27)46/h1-8,23,32H,11-22,24-25H2,(H,44,50)(H,45,47)(H,51,52,53) |
| InChIKey | ZUVGKZIBBJJSQX-UHFFFAOYSA-N |
Product Specification
| Storage | -20 °C |
Application
Sulfo DBCO-PEG4-TFP ester is a water-soluble, PEG4-spaced cyclooctyne (DBCO) click chemistry reagent that pairs strain-promoted azide–alkyne cycloaddition (SPAAC) labeling with a reactive TFP ester for acylation of primary amines. The amphiphilic sulfonate handle and PEG spacer support efficient handling in aqueous buffers, while the TFP ester enables rapid installation of the DBCO functionality onto amine-containing biomolecules and surfaces. This combination makes Sulfo DBCO-PEG4-TFP ester a widely used intermediate for building modular conjugates for chemical biology, imaging probe development, and functional biomaterials.
1. Bioconjugation With Amines
Sulfo DBCO-PEG4-TFP ester is commonly used to functionalize proteins, peptides, and other amine-bearing biomolecules with a DBCO handle, enabling subsequent SPAAC coupling to azide-tagged partners such as fluorophores, affinity tags, or nucleic-acid probes. The PEG4 spacing helps reduce steric constraints between the conjugated biomolecule and the click-reactive DBCO group, which is beneficial for maintaining binding or recognition behavior of the labeled construct. Researchers in chemical biology and molecular imaging frequently choose this reagent when they need a stable, aqueous-compatible route to install cyclooctyne functionality without relying on copper catalysts.
2. Surface And Material Functionalization
Sulfo DBCO-PEG4-TFP ester is well suited for modifying amine-present surfaces and biomaterials, including functionalized polymers, hydrogel matrices, and activated coatings where TFP esters react with surface-exposed primary amines. Once immobilized, the DBCO-bearing material can be used to capture azide-functional molecules via SPAAC, supporting downstream assembly of patterned interfaces, immobilized affinity reagents, and multivalent labeling schemes. Biomaterials and diagnostics developers often leverage the sulfonate and PEG spacer to improve dispersion and reduce nonspecific interactions during aqueous conjugation workflows.
3. Fluorophore And Probe Assembly
Sulfo DBCO-PEG4-TFP ester is frequently used as a precursor for generating imaging and sensing reagents that require a DBCO-modified scaffold prior to final labeling. By first attaching the DBCO functionality to an amine-containing targeting component (such as a labeled peptide carrier or a polymeric scaffold), the subsequent azide–DBCO click step can be used to introduce fluorophores, quencher groups, or other reporter moieties with high modularity. This workflow is attractive in molecular imaging and diagnostic reagent development because it separates the amine-acylation step from the final reporter installation, improving flexibility across probe formats.
4. Multivalent Targeting Platforms
Sulfo DBCO-PEG4-TFP ester supports the construction of multivalent conjugates where multiple DBCO sites are installed onto a macromolecular carrier or targeting ligand through TFP-ester acylation of accessible amines. The resulting DBCO-functional intermediate can then be reacted with azide-bearing components to create higher-order architectures, including crosslinked networks, branched conjugates, and combinatorial labeling sets. Chemical biology groups use this approach to tune the density and arrangement of reactive handles on large biomolecular assemblies, enabling efficient downstream click-based decoration while maintaining aqueous compatibility.
Computed Properties
| XLogP3 | 1.5 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 16 |
| Rotatable Bond Count | 24 |
| Exact Mass | 851.23470757 g/mol |
| Monoisotopic Mass | 851.23470757 g/mol |
| Topological Polar Surface Area | 205Ų |
| Heavy Atom Count | 59 |
| Formal Charge | 0 |
| Complexity | 1530 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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