Oligonucleotide Synthesis, RNA Raw Materials & Modification

2'-O-Propargyl-A (Bz) CE Phosphoramidite

Oligonucleotide Synthesis, RNA Raw Materials & Modification

製品番号CH65073CAS番号171486-59-2純度>=98%

製品画像はありません

製品概要

クイックビュー

製品ファミリー: Oligonucleotide Synthesis, RNA Raw Materials & Modification
分子式: C50H54N7O8P
分子量: 912.0
純度: >=98%

2'-O-Propargyl-A (Bz) CE Phosphoramidite is a click-handle RNA building block: 5'-O-(4,4'-dimethoxytrityl)-N6-benzoyl-2'-O-(prop-2-yn-1-yl)adenosine 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite. It is identified by CAS 171486-59-2, molecular formula C50H54N7O8P, molecular weight 912.0, PubChem CID 102119200, and InChIKey ZNKFQCJEZKZIPC-XOMUZYEBSA-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 N6-benzoyl base group is removed at final deprotection.

別名

5'-O-DMT-N6-Bz-2'-O-propargyladenosine 3'-CE phosphoramidite; 2'-O-(2-propynyl)-adenosine amidite

同定情報と仕様

Catalog No.	CH65073
CAS No.	171486-59-2
Molecular Formula	C50H54N7O8P
Molecular Weight	912.0
PubChem CID	102119200
InChIKey	ZNKFQCJEZKZIPC-XOMUZYEBSA-N
Purity	>=98%

保管条件

-20 C

技術属性

Monomer class: 2'-O-propargyl CE phosphoramidite
Nucleobase: Adenine
Conjugation handle: Terminal alkyne
Base protection: N6-benzoyl
Packaging: 5 mg; 10 mg; 25 mg; 50 mg; 100 mg; 200 mg; 250 mg; 500 mg; 1 g; 2 g; 5 g; 10 g; 100 g; Custom packaging on request
Water content: <=0.5%
Physical form: white to off-white powder
Stability: >=4 years

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 N6-benzoyl 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 102119200
PubChem · CID 102119200

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).

Is the propargyl group a protecting group that gets removed?

No. Unlike the 5'-DMT (removed each cycle) or the N6-benzoyl base group (removed at final deprotection), the 2'-O-propargyl ether is a permanent modification that stays on the finished oligonucleotide as the click handle.