C8-Alkyne-dUTP
Modified triphosphate for incorporation in PCR reaction
 
                        | Size | Catalog No. | Price | 
|---|---|---|
| 1 µmol | BCT-05-S | € 100,00 | 
| 5 µmol | BCT-05-L | € 300,00 | 
Chemical Properties
- 
                                                        Molecular Formula
                                                        C17H23N2O14P3 
- 
                                                        Shelf Life
                                                        12 months unopened after receipt 
- 
                                                        Storage Conditions
                                                        -20 °C 
- 
                                                        Molecular Weight
                                                        572.29 g/mol 
- 
                                                        Purity
                                                        ≥ 95% (HPLC) 
- 
                                                        Physical State
                                                        100 mM clear colorless 
 solution in water (pH 7.5)
- 
                                                        CAS Number
                                                        1004297-65-7 (free acid) 
- 
                                                        Absorption (max)
                                                        λmax = 292 nm 
- 
                                                        Ɛ (max)
                                                        11.000 cm-1M-1 
Product Information
A Click-Functionalized Nucleotide for DNA Labeling and Post-Synthetic Modification
C8-Alkyne-dUTP is a modified deoxyuridine triphosphate (dUTP) featuring a C8 alkyne group at the C5 position of the uracil base. It enables site-specific DNA labeling via Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC), supporting a wide range of downstream applications in molecular biology, diagnostics, and nanobiotechnology.
The Molecular Engine for DNA Functionalization and Bioorthogonal Chemistry
C8-Alkyne-dUTP introduces a chemically orthogonal alkyne moiety into DNA during enzymatic synthesis. This modification allows for precise post-synthetic conjugation with azide-bearing molecules, including fluorophores, biotin, peptides, and other functional groups. It is designed to overcome limitations in traditional nucleotide labeling strategies and expand the toolkit for DNA-based technologies.
Challenges in DNA Labeling and Modification
Prior to the development of click-functionalized nucleotides, researchers faced several limitations:
- Polymerase Compatibility
 Many modified nucleotides were poorly tolerated by DNA polymerases, resulting in inefficient incorporation.
- Limited Functional Labeling Options
 Conventional dUTPs lacked reactive groups for selective post-synthetic modification.
- Non-Specific Conjugation Chemistry
 Labeling often relied on NHS esters or maleimides, which lacked positional control and reproducibility.
C8-Alkyne-dUTP as a Bioorthogonal Solution
- Click-Ready Functionality
 The terminal alkyne group enables selective and efficient CuAAC reactions with azide-functionalized probes under mild conditions.
- High Incorporation Efficiency
 The C8 modification is positioned on the nucleobase, away from the polymerase active site, allowing incorporation by Taq, KOD, Vent, Pwo, and Deep Vent exo- polymerases.
- Versatile Post-Synthesis Labeling
 Once incorporated, the alkyne-modified base can be conjugated to a wide range of azide-bearing molecules without disrupting DNA structure or function.

Applications in Research and Biotechnology
- DNA Labeling
 Enables site-specific modifications for imaging, purification, and molecular tracking.
- Biotinylation and Affinity Tagging
 Facilitates streptavidin-based capture and purification of labeled DNA strands.
- PCR and Primer Extension
 Compatible with enzymatic incorporation for advanced genetic studies.
- DNA Nanotechnology
 Supports spatially controlled modification of DNA origami and nanostructures.
- Oligonucleotide–Drug Conjugates
 Enables site-specific attachment of small molecules or peptides for therapeutic and diagnostic use.
- Gene Silencing
 Enhances triplex-forming oligonucleotides (TFOs) with improved stability and gene-targeting efficiency.
- DNA Hydrogel Functionalization
 Allows post-synthetic modification of DNA hydrogels via CuAAC without compromising mechanical properties.
- Aptamer Discovery
 Used in Click-Particle Display for screening base-modified aptamers with enhanced binding properties.
- dNTP Quantification
 Provides a safer alternative to radioisotope-based assays using fluorophore conjugation.
LITERATURE
Synthesis of Highly Modified DNA by a Combination of PCR with Alkyne-Bearing Triphosphates and Click Chemistry, J. Gierlich et al., 2007, Chem. – A Eur. J., Vol. 13, p. 9486–9494.
https://doi.org/10.1002/chem.200700502
Directed DNA Metallization, G. A. Burley et al., 2006, J. Am. Chem. Soc., Vol. 128, p. 1398–1399.
https://doi.org/10.1021/ja055517v
Fluorescent labelling of in situ hybridisation probes through the copper-catalysed azide-alkyne cycloaddition reaction, S. Hesse et al., 2016, Chromosome Research, Vol. 24(3), p. 299–307.
https://doi.org/10.1007/s10577-016-9522-z
Enzymatic Synthesis of Chemical Nuclease Triplex-Forming Oligonucleotides with Gene-Silencing Applications, B. McGorman et al., 2022, Nucleic Acids Research, Vol. 50(10), p. 5467–5481.
https://doi.org/10.1093/nar/gkac438
Revolutionizing DNA: advanced modification techniques for next-gen nanotechnology, P. Panda et al., 2024, Nucleosides, Nucleotides & Nucleic Acids, 1–32.
https://doi.org/10.1080/15257770.2024.2432992
Modified Nucleosides, Nucleotides and Nucleic Acids via Click Azide-Alkyne Cycloaddition for Pharmacological Applications, D. Perrone et al., 2021, Molecules, Vol. 26(11), 3100.
https://doi.org/10.3390/molecules26113100
FAQ
- 
                                                    Is C8-Alkyne-dUTP compatible with standard DNA polymerases?                                                    
                                                    Yes. It is efficiently incorporated by Taq, KOD, Vent, Pwo, and Deep Vent exo- polymerases. 
- 
                                                    What types of molecules can be conjugated post-synthetically?                                                    
                                                    Azide-functionalized fluorophores, biotin, peptides, sugars, and small molecules. 
- 
                                                    Does the modification affect DNA structure or function?                                                    
                                                    No. The alkyne group is positioned to preserve DNA integrity and polymerase activity. 
- 
                                                    Can it be used in DNA origami or hydrogel systems?                                                    
                                                    Yes. It supports spatially controlled modification in nanostructures and hydrogels. 
- 
                                                    Is it suitable for aptamer screening?                                                    
                                                    Yes. It is used in Click-Particle Display for generating chemically modified aptamers. 
