Oligonucleotide Synthesis, RNA Raw Materials & Modification

3'-NH-Trt-2',3'-ddA (dmf) 5'-CE Phosphoramidite

Oligonucleotide Synthesis, RNA Raw Materials & Modification

产品编号CH65124CAS号1644649-86-4纯度99.98%

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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: C41H50N9O3P
分子量: 747.9
纯度: 99.98%

3'-NH-Trt-2',3'-ddA (dmf) 5'-CE Phosphoramidite is a building block for N3'→P5' phosphoramidate oligonucleotide chemistry: a 3'-tritylamino-2',3'-dideoxyadenosine with N6-dimethylformamidine protection and a 5'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite. Its PubChem-backed identity includes CAS 1644649-86-4, molecular formula C41H50N9O3P, molecular weight 747.9, PubChem CID 123695624, and InChIKey GYBKIQYITQGOTA-UHFFFAOYSA-N.

Unlike a standard amidite, the 3'-position carries a trityl-protected primary amine in place of the 3'-hydroxyl, and the phosphoramidite is on the 5'-position as a reverse amidite. During synthesis, the incoming monomer's 5'-phosphoramidite couples to the 3'-amino group of the growing chain, forming a P-N phosphoramidate bond (an N3'→P5' linkage) instead of the natural phosphodiester. Cited phosphoramidate literature reports nuclease-hydrolysis, duplex-stability, and RNA-like C3'-endo conformation context for this backbone class. The dmf group protects the adenine N6 amine and is removed during final deprotection.

同义词

3'-amino-3'-deoxy-2'-deoxyadenosine(dmf) 5'-CE phosphoramidite, 3'-N-trityl; N3'->P5' phosphoramidate A building block

身份与规格

Catalog No.	CH65124
CAS No.	1644649-86-4
Molecular Formula	C41H50N9O3P
Molecular Weight	747.9
PubChem CID	123695624
InChIKey	GYBKIQYITQGOTA-UHFFFAOYSA-N
Purity	99.98%

储存条件

-20 C

技术属性

Monomer class: 3'-NH-Trt reverse CE phosphoramidite
Nucleobase: Adenine
Base protection: N6-dimethylformamidine
Linkage role: N3'-to-P5' phosphoramidate
Grade: analytical grade
Packaging: 10 mg; 50 mg; 100 mg; 250 mg; 1 g; 5 g; 10 g; 50 g; 100 g; 500 g; 1 kg; 20 kg; Custom packaging on request
Physical form: solid
Stability: powder: 3 years; in solvent: 1 year

应用背景

N3'→P5' phosphoramidate linkage: the 3'-amino group couples to the next residue's 5'-phosphorus, forming a P-N phosphoramidate bond in place of a phosphodiester.
Reverse (5'-)amidite: the phosphoramidite is on the 5'-position and the 3'-amine is trityl-protected, so chain assembly runs in the 5'→3' sense for this chemistry.
Backbone literature context: cited N3'→P5' phosphoramidate literature reports nuclease-hydrolysis, duplex-stability, and RNA-like C3'-endo conformation context; the dmf group protects the adenine N6 amine.

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 123695624
PubChem · CID 123695624

常见问题

What is an N3'→P5' phosphoramidate?

It is a modified backbone linkage in which the phosphorus joins the 3'-nitrogen of one nucleoside to the 5'-oxygen of the next (a P-N bond), instead of the natural 3'-oxygen phosphodiester. It is built from 3'-amino-3'-deoxy nucleosides like this one.