5-ap-ddUTP (Amino-dideoxy-UTP)
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Product summary
Quick view
- Product family
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- MF
- C12H18N3O13P3
- MW
- 505.20
- Purity
- 98%
5-ap-ddUTP is 5-(3-aminopropargyl)-2',3'-dideoxyuridine-5'-triphosphate: a 2',3'-dideoxy UTP (a chain terminator) carrying a primary amine on a propargyl (alkyne) linker at the C5 of uracil. Key identifiers include CAS 114748-59-3, molecular formula C12H18N3O13P3, and molecular weight 505.20 (PubChem CID 11071202).
2',3'-dideoxynucleoside triphosphates act as specific chain-terminating inhibitors of DNA polymerase — the basis of Sanger dideoxy sequencing: once one is incorporated, the missing 3'-OH stops further extension. The C5 primary amine is a labelling handle for attaching a dye, so this reagent serves as a building block for labeled dye-terminators.
Synonyms
5-(3-aminopropargyl)-2',3'-dideoxyuridine-5'-triphosphate; amino-ddUTP
Identity and specifications
| Catalog No. | CH66019 |
| CAS No. | 114748-59-3 |
| Molecular Formula | C12H18N3O13P3 |
| Molecular Weight | 505.20 |
| PubChem CID | 11071202 |
| InChIKey | HOYCULDIPQRPFI-VHSXEESVSA-N |
| Purity | 98% |
Storage conditions
-20 C
Technical attributes
- Nucleotide class
- Chain-terminating ddNTP
- Nucleobase
- Uracil
- Base modification
- 5-(3-Aminopropargyl)
- Reactive handle
- Primary amine
- Packaging
- 1 mg; 25 mg; 50 mg; 100 mg; 250 mg; Custom packaging on request
- Solution concentration
- 100 mM
- Physical form
- solid; white to off-white
- Stability
- 12 months after delivery; cumulative ambient exposure up to 1 week possible
Application context
- Chain terminator: a 2',3'-dideoxy-UTP that stops DNA-polymerase extension when incorporated (the basis of Sanger sequencing).
- Amine label handle: the C5 aminopropargyl group lets a dye be attached, giving a labeled terminator.
- Dye-terminator building block: used to prepare fluorescent ddNTP terminators for sequencing.
Related technical resources
Oligonucleotide Modification
Sugar, base, backbone, terminal, and conjugation modifications for ASO, siRNA, guide RNA, aptamer, and research or labeling oligo projects.
Oligonucleotide Synthesis
Support for modified monomers, supports, sulfurizing reagents, cap analogs, and related oligo synthesis inputs.
Public references
- Sustainability Challenges and Opportunities in Oligonucleotide Manufacturing
Journal of Organic Chemistry, 2021
Product-family technical context
- Solid-phase supports for oligonucleotide synthesis
Current Protocols in Nucleic Acid Chemistry, 2013
Product-family technical context
- Deoxynucleoside phosphoramidites—A new class of key intermediates for deoxypolynucleotide synthesis
Tetrahedron Letters, 1981
Product-family technical context
- Synthesis of deoxyoligonucleotides on a polymer support
Journal of the American Chemical Society, 1981
Product-family technical context
- PubChem Compound 11071202
PubChem · CID 11071202
Frequently Asked Questions
What is 5-ap-ddUTP used for?
It is a 2',3'-dideoxy-UTP chain terminator with a C5 aminopropargyl amine handle. As a dideoxy nucleotide it stops DNA-polymerase extension (the basis of Sanger sequencing); the amine allows a dye to be attached, making it a building block for labeled dye-terminators.
Why does the dideoxy nucleotide terminate synthesis?
A 2',3'-dideoxynucleotide lacks the 3'-hydroxyl needed to form the next internucleotide bond. Once a polymerase incorporates it, extension stops — the principle behind dideoxy (Sanger) sequencing.
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