Oligonucleotide Synthesis, RNA Raw Materials & Modification

5'-(E)-VP-2'-OMe-A (Bz) Phosphoramidite

Oligonucleotide Synthesis, RNA Raw Materials & Modification

产品编号CH65120CAS号2419895-65-9纯度99% (HPLC)

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产品概述

快速信息

产品系列: Oligonucleotide Synthesis, RNA Raw Materials & Modification
分子式: C40H57N7O12P2
分子量: 889.9
纯度: 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.

同义词

5'-(E)-vinylphosphonate-2'-OMe-A(Bz) 3'-CE phosphoramidite; 5'-VP-2'-OMe-rA(Bz) amidite (5'-terminal)

身份与规格

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)

储存条件

below -20 C

技术属性

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

应用背景

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.

公开来源

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 化合物 172878654
PubChem · CID 172878654

常见问题

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.