2'-O-Propargyl Guanosine (2'-O-Propargyl G)
2′-O-Propargyl Guanosine (2′-O-Propargyl G) is a modified RNA nucleotide in which the natural 2′-hydroxyl group of ribose is replaced with a propargyl (–CH₂–C≡CH) substituent. The terminal alkyne provides a chemically selective bioorthogonal handle for post-synthetic functionalization while preserving the guanine nucleobase for standard base pairing with cytosine.
This modification is widely used in click chemistry because the terminal alkyne reacts efficiently with azide-containing molecules through copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). Following incorporation into RNA during solid-phase synthesis, the oligonucleotide can be conjugated to fluorophores, biotin, PEG, peptides, lipids, nanoparticles, antibodies, carbohydrates, and numerous other functional molecules.
Compared with terminal alkyne modifications placed at the 5′ or 3′ end, 2′-O-Propargyl G allows site-specific internal labeling, enabling precise placement of functional groups within the RNA sequence. This is particularly valuable for mechanistic studies, RNA imaging, structural biology, biosensors, and therapeutic oligonucleotide development.
Bio-Synthesis offers custom 2′-O-Propargyl G-modified RNA oligonucleotides for:
- RNA probes
- siRNA
- miRNA
- Aptamers
- sgRNA and CRISPR guide RNAs
- Antisense oligonucleotides
- Ribozymes
- RNA structural studies
- Therapeutic RNA research
Typical applications include:
- Copper-catalyzed click chemistry (CuAAC)
- Bioorthogonal labeling
- Fluorescent RNA preparation
- Biotin conjugation
- PEGylation
- Peptide conjugation
- Lipid conjugation
- RNA imaging
- RNA pull-down assays
- Biosensor development
- Nanotechnology
- Therapeutic oligonucleotide conjugation
Technical Notes
- Chemistry type:RNA phosphoramidite for solid-phase oligonucleotide synthesis.
- Not an NHS reagent.
- Primary reaction: CuAAC click chemistry with azide-containing molecules.
Typical Specifications
| Property |
Specification |
| Modification |
2′-O-Propargyl Guanosine |
| Abbreviation |
2′-O-Propargyl G (2′-O-Propargyl-rG) |
| Modification Type |
2′-O Sugar Modification |
| Reactive Group |
Terminal alkyne |
| Click Chemistry |
CuAAC (Copper-catalyzed azide-alkyne cycloaddition) |
| Base Pairing |
Pairs with cytosine (C) |
| Typical Placement |
Internal RNA position |
| Compatible Oligonucleotides |
RNA, siRNA, miRNA, sgRNA, aptamers, ASOs |
| Typical Applications |
Click chemistry, fluorescent labeling, biotinylation, PEGylation, peptide conjugation, RNA imaging, pull-down assays, biosensors |
Product Information
2'-O-Propargyl Guanosine (2'-O-Propargyl G)
2′-Modified RNA, Click Chemistry
-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:
- Jao CY, Salic A. Exploring RNA transcription and turnover in vivo by using click chemistry. Proceedings of the National Academy of Sciences USA. 2008;105(41):15779-15784.
- Gramlich PME, Warncke S, Gierlich J, Carell T. Click-click-click: single to triple modification of DNA. Angewandte Chemie International Edition. 2008;47:3442-3444.
- Kolb HC, Finn MG, Sharpless KB. Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angewandte Chemie International Edition. 2001;40:2004-2021.
- Hermanson GT. Bioconjugate Techniques. 3rd Edition. Academic Press; 2013.
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