Oligonucleotide Synthesis, RNA Raw Materials & Modification

2'-O-Propargyl-C (Ac) CE Phosphoramidite

Oligonucleotide Synthesis, RNA Raw Materials & Modification

製品番号CH65074CAS番号1498305-51-3純度98%

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製品概要

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製品ファミリー: Oligonucleotide Synthesis, RNA Raw Materials & Modification
分子式: C44H52N5O9P
分子量: 825.9
純度: 98%

2'-O-Propargyl-C (Ac) CE Phosphoramidite is a click-handle RNA building block: 5'-O-(4,4'-dimethoxytrityl)-N4-acetyl-2'-O-(prop-2-yn-1-yl)cytidine 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite. It is identified by CAS 1498305-51-3, molecular formula C44H52N5O9P, molecular weight 825.9, PubChem CID 170899159, and InChIKey JIMYWWYYWAHJAD-ZMHKPELYSA-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. The monomer couples through a standard 3'-phosphoramidite (3'→5' linkages), the 5'-DMT is removed each cycle, and the N4-acetyl base group is removed at final deprotection.

別名

5'-O-DMT-N4-Ac-2'-O-propargylcytidine 3'-CE phosphoramidite; 2'-O-(2-propynyl)-cytidine amidite

同定情報と仕様

Catalog No.	CH65074
CAS No.	1498305-51-3
Molecular Formula	C44H52N5O9P
Molecular Weight	825.9
PubChem CID	170899159
InChIKey	JIMYWWYYWAHJAD-ZMHKPELYSA-N
Purity	98%

保管条件

-20 C

技術属性

Monomer class: 2'-O-propargyl CE phosphoramidite
Nucleobase: Cytosine
Conjugation handle: Terminal alkyne
Base protection: N4-acetyl
Packaging: 100 mg; 250 mg; 500 mg; 1 g; 5 g; 10 g; 100 g; 1 kg; Custom packaging on request
Physical form: white, off-white to faint yellow powder

用途情報

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; the 5'-DMT is removed each cycle and the N4-acetyl base-protecting group is removed during final deprotection.

公開情報源

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 170899159
PubChem · CID 170899159

よくある質問

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).

Why is the cytosine acetyl-protected?

The N4-acetyl group masks the cytosine exocyclic amine during synthesis and is removed at final deprotection. The 5'-DMT is removed each coupling cycle, while the 2'-O-propargyl ether stays on the finished oligonucleotide as the click handle.