Oligonucleotide Synthesis, RNA Raw Materials & Modification

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

Oligonucleotide Synthesis, RNA Raw Materials & Modification

製品番号CH65128CAS番号195375-64-5純度>=98%

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製品概要

クイックビュー

製品ファミリー: Oligonucleotide Synthesis, RNA Raw Materials & Modification
分子式: C45H49N8O4P
分子量: 796.9
純度: >=98%

3'-NH-Trt-2',3'-ddA (Bz) 5'-CE Phosphoramidite is a building block for N3'→P5' phosphoramidate oligonucleotide chemistry: a 3'-tritylamino-2',3'-dideoxyadenosine with N6-benzoyl protection and a 5'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite. It is the N6-benzoyl counterpart of the N6-dimethylformamidine (dmf) variant. Its PubChem-backed identity includes CAS 195375-64-5, molecular formula C45H49N8O4P, molecular weight 796.9, PubChem CID 10557285, and InChIKey WFMJBNBVXHQESI-YWGGCHKGSA-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. N6-benzoyl protects the adenine amine and is removed during final deprotection.

別名

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

同定情報と仕様

Catalog No.	CH65128
CAS No.	195375-64-5
Molecular Formula	C45H49N8O4P
Molecular Weight	796.9
PubChem CID	10557285
InChIKey	WFMJBNBVXHQESI-YWGGCHKGSA-N
Purity	>=98%

保管条件

-18 C

技術属性

Monomer class: 3'-NH-Trt reverse CE phosphoramidite
Nucleobase: Adenine
Base protection: N6-benzoyl
Linkage role: N3'-to-P5' phosphoramidate
Packaging: 500 mg; 1 g; 5 g; 10 g; 25 g; 50 g; 100 g; 500 g; 1 kg; 5 kg; 25 kg; Custom packaging on request

用途情報

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; N6-benzoyl protects the adenine amine.

公開情報源

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 10557285
PubChem · CID 10557285

よくある質問

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.

How does this differ from the dmf-protected adenosine version?

This is the N6-benzoyl (Bz)-protected adenosine building block; the other variant uses an N6-dimethylformamidine (dmf) group on the adenine amine. Both are N3'→P5' phosphoramidate building blocks and differ in the base protecting group.