2'-Deoxyadenosine (Bz) CE Reverse Phosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Product summary
Quick view
- Product family
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- MF
- C47H52N7O7P
- MW
- 857.9
- Purity
- >=98.0% (HPLC)
2'-Deoxyadenosine (Bz) CE Reverse Phosphoramidite is the reverse-orientation 2'-deoxyadenosine building block for DNA synthesis: N6-benzoyl-2'-deoxyadenosine with a 3'-O-(4,4'-dimethoxytrityl) group and a 5'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite group. CH65050 is identified by CAS 140712-82-9, molecular formula C47H52N7O7P, molecular weight 857.9, PubChem CID 17998961, and InChIKey JMABKCCHUAJFJE-AKWFTNRHSA-N.
Unlike a standard amidite (DMT on 5', phosphoramidite on 3'), the reverse amidite has the DMT on the 3'-hydroxyl and the phosphoramidite on the 5'-hydroxyl, so chain elongation proceeds in the 5'→3' direction. The acid-labile 3'-DMT is removed each cycle, and the N6-benzoyl base group is removed at final deprotection.
Synonyms
reverse DMT-dA(Bz) phosphoramidite; 3'-O-DMT-N6-benzoyl-2'-deoxyadenosine 5'-CE phosphoramidite
Identity and specifications
| Catalog No. | CH65050 |
| CAS No. | 140712-82-9 |
| Molecular Formula | C47H52N7O7P |
| Molecular Weight | 857.9 |
| PubChem CID | 17998961 |
| InChIKey | JMABKCCHUAJFJE-AKWFTNRHSA-N |
| Purity | >=98.0% (HPLC) |
Storage conditions
-20 C
Technical attributes
- Monomer class
- Reverse DNA CE phosphoramidite
- Nucleobase
- Adenine
- DMT position
- 3'-O
- Coupling position
- 5'-O phosphoramidite
- Grade
- N (Normal)
- Packaging
- 100 mg; 250 mg; 500 mg; 1 g; 2 g; 5 g; 10 g; 100 g; Custom packaging on request
- Water content
- <=0.5%
- Physical form
- white to off-white powder
- Stability
- same in solution as standard dA phosphoramidite
Application context
- 5'→3' DNA coupling monomer: the 5'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite is the reactive coupling group, so oligonucleotides grow in the 5'→3' direction (reverse of standard synthesis).
- 3'-DMT protection: the acid-labile 4,4'-dimethoxytrityl group is on the 3'-hydroxyl and is removed at the start of each chain-elongation cycle.
- N6-benzoyl base protection: the benzoyl group masks the adenine exocyclic amine during synthesis and is removed at final deprotection.
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 17998961
PubChem · CID 17998961
Frequently Asked Questions
What makes this a 'reverse' phosphoramidite?
In a standard amidite the DMT is on the 5'-hydroxyl and the phosphoramidite on the 3'-hydroxyl. Here they are swapped — 3'-DMT and 5'-phosphoramidite — so the oligonucleotide is assembled in the 5'→3' direction instead of the usual 3'→5'.
How does it relate to the standard 2'-deoxyadenosine (Bz) phosphoramidite?
It has the same N6-benzoyl-2'-deoxyadenosine core but the DMT and phosphoramidite are on the opposite hydroxyls (3' vs 5'). The standard (3'-phosphoramidite) dA(Bz) amidite is cataloged separately.
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