5-ap-ddUTP (Amino-dideoxy-UTP)
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Produktübersicht
Kurzüberblick
- Produktfamilie
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- MF
- C12H18N3O13P3
- MW
- 505.20
- Reinheit
- 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.
Synonyme
5-(3-aminopropargyl)-2',3'-dideoxyuridine-5'-triphosphate; amino-ddUTP
Identität und Spezifikationen
| Catalog No. | CH66019 |
| CAS No. | 114748-59-3 |
| Molecular Formula | C12H18N3O13P3 |
| Molecular Weight | 505.20 |
| PubChem CID | 11071202 |
| InChIKey | HOYCULDIPQRPFI-VHSXEESVSA-N |
| Purity | 98% |
Lagerbedingungen
-20 C
Technische Merkmale
- 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
Anwendungskontext
- 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.
Zugehörige technische Ressourcen
Öffentliche Quellen
- 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-Verbindung 11071202
PubChem · CID 11071202
Häufig gestellte Fragen
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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