2'-O-Propargyl-C (Ac) CE Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Résumé du produit
Aperçu rapide
- Famille de produits
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- FM
- C44H52N5O9P
- PM
- 825.9
- Pureté
- 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.
Synonymes
5'-O-DMT-N4-Ac-2'-O-propargylcytidine 3'-CE phosphoramidite; 2'-O-(2-propynyl)-cytidine amidite
Identité et spécifications
| Catalog No. | CH65074 |
| CAS No. | 1498305-51-3 |
| Molecular Formula | C44H52N5O9P |
| Molecular Weight | 825.9 |
| PubChem CID | 170899159 |
| InChIKey | JIMYWWYYWAHJAD-ZMHKPELYSA-N |
| Purity | 98% |
Conditions de stockage
-20 C
Caractéristiques techniques
- 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
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 N4-acetyl 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 170899159
PubChem · CID 170899159
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).
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.
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