3'-NH-Trt-2',3'-ddA (Bz) 5'-CE Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Produktübersicht
Kurzüberblick
- Produktfamilie
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- MF
- C45H49N8O4P
- MW
- 796.9
- Reinheit
- >=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.
Synonyme
3'-amino-3'-deoxy-2'-deoxyadenosine(Bz) 5'-CE phosphoramidite, 3'-N-trityl; N3'->P5' phosphoramidate A(Bz) building block
Identität und Spezifikationen
| Catalog No. | CH65128 |
| CAS No. | 195375-64-5 |
| Molecular Formula | C45H49N8O4P |
| Molecular Weight | 796.9 |
| PubChem CID | 10557285 |
| InChIKey | WFMJBNBVXHQESI-YWGGCHKGSA-N |
| Purity | >=98% |
Lagerbedingungen
-18 C
Technische Merkmale
- 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
Anwendungskontext
- 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.
Zugehörige technische Ressourcen
Öffentliche Quellen
- 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-Verbindung 10557285
PubChem · CID 10557285
Häufig gestellte Fragen
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.
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