BCN-PEG3
BCN-PEG3 is a highly versatile bioorthogonal click chemistry modification that combines a reactive bicyclo[6.1.0]nonyne (BCN) cyclooctyne with a flexible PEG3 (triethylene glycol) spacer. The strained BCN moiety reacts rapidly and selectively with azide-functionalized molecules through strain-promoted azide-alkyne cycloaddition (SPAAC), producing stable triazole linkages without the need for a copper catalyst. This catalyst-free reaction is particularly advantageous for conjugating sensitive biomolecules, therapeutic oligonucleotides, and living cells where copper may be cytotoxic.
The PEG3 spacer provides greater flexibility and hydrophilicity than direct BCN attachment while remaining relatively compact. The additional spacing improves accessibility of the BCN group, reduces steric hindrance during conjugation, and can enhance reaction efficiency with larger biomolecules such as antibodies, proteins, peptides, enzymes, polymers, lipids, and nanoparticles. The PEG3 linker also improves aqueous solubility while minimizing nonspecific interactions.
BCN-PEG3 reacts efficiently with a broad range of azide-containing molecules, including Azido C6, Azido PEG linkers, azide-modified peptides, proteins, fluorescent dyes, lipids, polymers, glycans, and nanoparticles. The resulting triazole linkage is chemically stable and compatible with physiological buffers, making BCN-PEG3 an excellent choice for both research and therapeutic development.
Bio-Synthesis offers custom BCN-PEG3-modified oligonucleotides for DNA, RNA, PNA, LNA, siRNA, antisense oligonucleotides (ASOs), aptamers, molecular beacons, CRISPR guide RNAs, and other synthetic nucleic acids. BCN-PEG3 may be incorporated at the 5′ terminus, 3′ terminus, or selected internal positions and is compatible with numerous additional modifications including fluorophores, quenchers, biotin, thiol modifiers, amino modifiers, GalNAc, cholesterol, PEG linkers, peptide conjugates, antibody conjugates, lipid conjugates, and nanoparticle conjugates.
Typical applications include:
- Copper-free SPAAC click chemistry
- Antibody-oligonucleotide conjugates (AOCs)
- Protein-oligonucleotide conjugates
- Peptide conjugation
- Fluorescent dye conjugation
- Nanoparticle functionalization
- Aptamer conjugation
- DNA nanotechnology
- Cell surface labeling
- Targeted therapeutic research
Each modified oligonucleotide is synthesized using high-quality solid-phase phosphoramidite chemistry and is available with optional HPLC or PAGE purification. Comprehensive analytical characterization includes HPLC, LC-MS, MALDI-TOF, UV spectroscopy, and additional quality control testing to verify sequence identity, purity, and successful incorporation of the BCN-PEG3 modification.
| Property |
Typical Value |
| Modification |
BCN-PEG3 |
| Reactive Group |
BCN (Bicyclo[6.1.0]nonyne) |
| Spacer |
PEG3 (Triethylene glycol) |
| Click Chemistry |
SPAAC (Copper-free) |
| Reaction Partner |
Azide-functionalized molecules |
| Catalyst Required |
None |
| Typical Attachment |
5′ end, 3′ end, or internal modification |
| Compatible Oligos |
DNA, RNA, PNA, LNA, siRNA, ASO, Aptamers |
| Typical Applications |
SPAAC conjugation, protein conjugation, antibody conjugation, fluorescent labeling, nanoparticle functionalization |
Product Information
cyclooctyne click chemistry modification
-20°C To -70°C
Oligonucleotides are stable in solution at 4°C for up to 2 weeks. Properly reconstituted material stored at -20°C should be stable for at least 6 months. Dried DNA (when kept at 20°C) in a nuclease-free environment should be stable for years.
References/Citations:
- Jewett JC, Bertozzi CR. Cu-free click cycloaddition reactions in chemical biology. Chemical Society Reviews. 2010;39:1272-1279. DOI: 10.1039/B901970G
- Dommerholt J, Rutjes FPJT, van Delft FL. Strain-promoted 1,3-dipolar cycloaddition of cycloalkynes and organic azides. Topics in Current Chemistry. 2016;374:16. DOI: 10.1007/s41061-016-0039-6
- Sletten EM, Bertozzi CR. Bioorthogonal chemistry: Fishing for selectivity in a sea of functionality. Angewandte Chemie International Edition. 2009;48(38):6974-6998. DOI: 10.1002/anie.200900942
- Hermanson GT. Bioconjugate Techniques. 3rd ed. Academic Press; 2013.
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