Oligonucleotide Synthesis, RNA Raw Materials & Modification

5'-(E)-VP-2'-OMe-U Phosphoramidite

Oligonucleotide Synthesis, RNA Raw Materials & Modification

产品编号CH65121CAS号2172373-55-4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: C32H52N4O13P2
分子量: 762.7
纯度: 99% (HPLC)

5'-(E)-VP-2'-OMe-U Phosphoramidite is a 5'-terminal building block for a 5'-(E)-vinylphosphonate phosphate-mimic motif: a 2'-O-methyluridine 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 2172373-55-4, molecular formula C32H52N4O13P2, molecular weight 762.7, and PubChem CID 172639621.

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. Uracil has no exocyclic amine, so no base protecting group is needed. Cited 2'-OMe literature provides RNA-binding and nuclease-stability context for the 2'-O-methyl group, and the protected vinylphosphonate amidite format is cited for solid-phase synthesis.

同义词

5'-(E)-vinylphosphonate-2'-OMe-U 3'-CE phosphoramidite; 5'-VP-2'-OMe-rU amidite (5'-terminal)

身份与规格

Catalog No.	CH65121
CAS No.	2172373-55-4
Molecular Formula	C32H52N4O13P2
Molecular Weight	762.7
PubChem CID	172639621
InChIKey	AJJPYIXDIHURAB-FQIYNDLNSA-N
Purity	99% (HPLC)

储存条件

-20 C

技术属性

Monomer class: 5'-(E)-vinylphosphonate phosphoramidite
Nucleobase: Uracil
Sugar modification: 2'-O-methyl
Terminal motif: 5'-(E)-vinylphosphonate
Packaging: 10 mg; 100 mg; 250 mg; 500 mg; 1 g; 5 g; 10 g; 25 g; 50 g; 100 g; 500 g; 1 kg; 2 kg; 5 kg; 25 kg; Custom packaging on request
Solution concentration: 10 mM in DMSO; 1 mL presentation
Water content: <=0.5%
Physical form: white to off-white powder
Stability: >=4 years

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; uracil needs no base protection.

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 172639621
PubChem · CID 172639621

常见问题

Why is this monomer a 5'-terminal residue, and why does it need no base protection?

The vinylphosphonate occupies the 5'-position (in place of the usual 5'-DMT), so it is added last, at the 5'-end. Uracil has no reactive exocyclic amine, so no base protecting group is required.