2'-O-Propargyl-A (Bz) CE Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Résumé du produit
Aperçu rapide
- Famille de produits
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- FM
- C50H54N7O8P
- PM
- 912.0
- Pureté
- >=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.
Synonymes
5'-O-DMT-N6-Bz-2'-O-propargyladenosine 3'-CE phosphoramidite; 2'-O-(2-propynyl)-adenosine amidite
Identité et spécifications
| Catalog No. | CH65073 |
| CAS No. | 171486-59-2 |
| Molecular Formula | C50H54N7O8P |
| Molecular Weight | 912.0 |
| PubChem CID | 102119200 |
| InChIKey | ZNKFQCJEZKZIPC-XOMUZYEBSA-N |
| Purity | >=98% |
Conditions de stockage
-20 C
Caractéristiques techniques
- 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
Contexte d’application
- 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.
Ressources techniques associées
Sources publiques
- 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
- Composé PubChem 102119200
PubChem · CID 102119200
Questions fréquentes
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.
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