2'-O-Propargyl-G (iBu) CE Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Résumé du produit
Aperçu rapide
- Famille de produits
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- FM
- C47H56N7O9P
- PM
- 894.0
- Pureté
- >=98%
2'-O-Propargyl-G (iBu) CE Phosphoramidite is a click-handle RNA building block: 5'-O-(4,4'-dimethoxytrityl)-N2-isobutyryl-2'-O-(prop-2-yn-1-yl)guanosine 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite. It is identified by CAS 171486-61-6, molecular formula C47H56N7O9P, molecular weight 894.0, PubChem CID 137126455, and InChIKey AGWGPRXHCUPJJO-VCGWOZLGSA-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 N2-isobutyryl base group is removed at final deprotection.
Synonymes
5'-O-DMT-N2-iBu-2'-O-propargylguanosine 3'-CE phosphoramidite; 2'-O-(2-propynyl)-guanosine amidite
Identité et spécifications
| Catalog No. | CH65075 |
| CAS No. | 171486-61-6 |
| Molecular Formula | C47H56N7O9P |
| Molecular Weight | 894.0 |
| PubChem CID | 137126455 |
| InChIKey | AGWGPRXHCUPJJO-VCGWOZLGSA-N |
| Purity | >=98% |
Conditions de stockage
below -20 C
Caractéristiques techniques
- Monomer class
- 2'-O-propargyl CE phosphoramidite
- Nucleobase
- Guanine
- Conjugation handle
- Terminal alkyne
- Base protection
- N2-isobutyryl
- 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; 1 kg; Custom packaging on request
- Physical form
- white, off-white to faint yellow powder
- Stability
- powder 3 years; in solvent 1 year
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 N2-isobutyryl 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 137126455
PubChem · CID 137126455
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 guanine isobutyryl-protected?
The N2-isobutyryl group masks the guanine 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.
Produits similaires
Besoin d’aide pour sélectionner un matériau ?
CHEMOS peut examiner l’adéquation produit, la structure cible, les questions de voie, les attentes analytiques et les besoins d’approvisionnement du projet.