5'-(E)-VP-2'-OMe-A (Bz) Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Product summary
Quick view
- Product family
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- MF
- C40H57N7O12P2
- MW
- 889.9
- Purity
- 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.
Synonyms
5'-(E)-vinylphosphonate-2'-OMe-A(Bz) 3'-CE phosphoramidite; 5'-VP-2'-OMe-rA(Bz) amidite (5'-terminal)
Identity and specifications
| 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) |
Storage conditions
below -20 C
Technical attributes
- 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
Application context
- 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.
Related technical resources
Oligonucleotide Modification
Sugar, base, backbone, terminal, and conjugation modifications for ASO, siRNA, guide RNA, aptamer, and research or labeling oligo projects.
Oligonucleotide Synthesis
Support for modified monomers, supports, sulfurizing reagents, cap analogs, and related oligo synthesis inputs.
Public references
- 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 Compound 172878654
PubChem · CID 172878654
Frequently Asked Questions
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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