5'-(E)-VP-2'-OMe-A (Bz) Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Résumé du produit
Aperçu rapide
- Famille de produits
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- FM
- C40H57N7O12P2
- PM
- 889.9
- Pureté
- 99% (HPLC)
5'-(E)-VP-2'-OMe-A (Bz) Phosphoramidite is a 5'-terminal building block for a 5'-(E)-vinylphosphonate phosphate-mimic motif: a 2'-O-methyl-N6-benzoyladenosine carrying a protected 5'-(E)-vinylphosphonate group at the 5'-position and a 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite. Its PubChem-backed identity includes CAS 2419895-65-9, molecular formula C40H57N7O12P2, molecular weight 889.9, and PubChem CID 172878654.
Cited literature describes 5'-(E)-vinylphosphonate (5'-VP) as a metabolically stable mimic of the natural 5'-monophosphate, where the bridging 5'-oxygen is replaced by a vinyl carbon. Because the 5'-position carries the vinylphosphonate in place of the usual 5'-DMT, this monomer is the 5'-terminal residue, added last. Cited 2'-OMe literature provides RNA-binding and nuclease-stability context for the 2'-O-methyl group, and N6-benzoyl protection is removed during final deprotection. The protected vinylphosphonate amidite format is cited for solid-phase synthesis.
Synonymes
5'-(E)-vinylphosphonate-2'-OMe-A(Bz) 3'-CE phosphoramidite; 5'-VP-2'-OMe-rA(Bz) amidite (5'-terminal)
Identité et spécifications
| Catalog No. | CH65120 |
| CAS No. | 2419895-65-9 |
| Molecular Formula | C40H57N7O12P2 |
| Molecular Weight | 889.9 |
| PubChem CID | 172878654 |
| InChIKey | DCUPCJOKPAHCLB-OZKJWBRJSA-N |
| Purity | 99% (HPLC) |
Conditions de stockage
below -20 C
Caractéristiques techniques
- Monomer class
- 5'-(E)-vinylphosphonate phosphoramidite
- Nucleobase
- Adenine
- Sugar modification
- 2'-O-methyl
- Terminal motif
- 5'-(E)-vinylphosphonate
- Packaging
- 10 mg; 25 mg; 50 mg; 100 mg; 1 g; 10 g; 50 g; 100 g; 500 g; 1 kg; 2 kg; 5 kg; 10 kg; 25 kg; Custom packaging on request
- Water content
- <=0.5%
- Physical form
- white to off-white powder
Contexte d’application
- 5'-phosphate mimic context: provides a 5'-(E)-vinylphosphonate at the 5'-terminus, described in cited literature as a metabolically stable 5'-phosphate mimic.
- 5'-terminal residue: the vinylphosphonate occupies the 5'-position (in place of 5'-DMT), so this monomer is added last in the synthesis.
- 2'-OMe modification: cited 2'-OMe literature provides RNA-binding and nuclease-stability context; N6-benzoyl protection 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 172878654
PubChem · CID 172878654
Questions fréquentes
Why is this monomer a 5'-terminal residue, and why are there two phosphorus atoms?
The vinylphosphonate occupies the 5'-position (in place of the usual 5'-DMT), so it is added last, at the 5'-end. The two phosphorus atoms are the vinylphosphonate group and the 3'-phosphoramidite coupling group.
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