Oligonucleotide Synthesis, RNA Raw Materials & Modification

5-ap-ddUTP (Amino-dideoxy-UTP)

Oligonucleotide Synthesis, RNA Raw Materials & Modification

产品编号CH66019CAS号114748-59-3纯度98%

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产品概述

快速信息

产品系列: Oligonucleotide Synthesis, RNA Raw Materials & Modification
分子式: C12H18N3O13P3
分子量: 505.20
纯度: 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.

同义词

5-(3-aminopropargyl)-2',3'-dideoxyuridine-5'-triphosphate; amino-ddUTP

身份与规格

Catalog No.	CH66019
CAS No.	114748-59-3
Molecular Formula	C12H18N3O13P3
Molecular Weight	505.20
PubChem CID	11071202
InChIKey	HOYCULDIPQRPFI-VHSXEESVSA-N
Purity	98%

储存条件

-20 C

技术属性

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

应用背景

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.

公开来源

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 化合物 11071202
PubChem · CID 11071202

常见问题

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.