3'-NH-Trt-2',3'-ddA (Bz) 5'-CE Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Product summary
Quick view
- Product family
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- MF
- C45H49N8O4P
- MW
- 796.9
- Purity
- >=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.
Synonyms
3'-amino-3'-deoxy-2'-deoxyadenosine(Bz) 5'-CE phosphoramidite, 3'-N-trityl; N3'->P5' phosphoramidate A(Bz) building block
Identity and specifications
| Catalog No. | CH65128 |
| CAS No. | 195375-64-5 |
| Molecular Formula | C45H49N8O4P |
| Molecular Weight | 796.9 |
| PubChem CID | 10557285 |
| InChIKey | WFMJBNBVXHQESI-YWGGCHKGSA-N |
| Purity | >=98% |
Storage conditions
-18 C
Technical attributes
- 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
Application context
- 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.
Related technical resources
Oligonucleotide Modification
Sugar, base, backbone, terminal, and conjugation modifications for ASO, siRNA, guide RNA, aptamer, and research or labeling oligo projects.
Oligonucleotide Synthesis
Support for modified monomers, supports, sulfurizing reagents, cap analogs, and related oligo synthesis inputs.
Public references
- 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 Compound 10557285
PubChem · CID 10557285
Frequently Asked Questions
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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