Oligonucleotide Synthesis, RNA Raw Materials & Modification

2'-O-Propargyl-U CE Phosphoramidite

Oligonucleotide Synthesis, RNA Raw Materials & Modification

产品编号CH65076CAS号171486-62-7纯度99.98%

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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: C42H49N4O9P
分子量: 784.8
纯度: 99.98%

2'-O-Propargyl-U CE Phosphoramidite is a click-handle RNA building block: 5'-O-(4,4'-dimethoxytrityl)-2'-O-(prop-2-yn-1-yl)uridine 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite. It is identified by CAS 171486-62-7, molecular formula C42H49N4O9P, molecular weight 784.8, PubChem CID 102390146, and InChIKey SKUHDLBLPLSZJC-CYSIDSPMSA-N.

The 2'-O-propargyl group is a permanent 2'-O-ether that carries a terminal alkyne (C≡CH) — it is not a protecting group. That terminal alkyne is a "click" handle: oligonucleotides bearing a terminal alkyne can be labeled after synthesis by the copper-catalyzed azide-alkyne cycloaddition (CuAAC) with azide-bearing reporters. Uracil has no exocyclic amine, so no base protecting group is needed; the monomer couples through a standard 3'-phosphoramidite (3'→5' linkages) and the 5'-DMT is removed each cycle.

同义词

5'-O-DMT-2'-O-propargyluridine 3'-CE phosphoramidite; 2'-O-(2-propynyl)-uridine amidite

身份与规格

Catalog No.	CH65076
CAS No.	171486-62-7
Molecular Formula	C42H49N4O9P
Molecular Weight	784.8
PubChem CID	102390146
InChIKey	SKUHDLBLPLSZJC-CYSIDSPMSA-N
Purity	99.98%

储存条件

-20 C

技术属性

Monomer class: 2'-O-propargyl CE phosphoramidite
Nucleobase: Uracil
Conjugation handle: Terminal alkyne
Base protection: None required
Packaging: 10 mg; 50 mg; 100 mg; 250 mg; 500 mg; 1 g; 5 g; 10 g; 100 g; 1 kg; Custom packaging on request
Physical form: solid
Stability: powder 3 years; in solvent 1 year

应用背景

Internal click handle: the 2'-O-propargyl ether places a terminal alkyne at the 2'-position for post-synthetic conjugation.
CuAAC labeling: the terminal alkyne reacts with azide-bearing reporters (dyes, biotin, other tags) by the copper-catalyzed azide-alkyne cycloaddition (click chemistry).
3'→5' coupling monomer: the 3'-phosphoramidite couples to form 3'→5' linkages and the 5'-DMT is removed each cycle. Uracil needs no base protecting group.

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 102390146
PubChem · CID 102390146

常见问题

What does the 2'-O-propargyl group provide?

It is a permanent 2'-O-ether that carries a terminal alkyne. The alkyne is a 'click' handle: after synthesis, the oligonucleotide can be conjugated to azide-bearing reporters (dyes, biotin, etc.) by the copper-catalyzed azide-alkyne cycloaddition (CuAAC).

Does the 2'-O-propargyl-U amidite need a base protecting group?

No. Uracil has no reactive exocyclic amine, so it needs no base protection. The monomer carries a 5'-O-DMT group (removed each cycle) and a 3'-phosphoramidite coupling group; the 2'-O-propargyl ether stays on the finished oligonucleotide as the click handle.